Journal articles: 'Hydrazone'

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Kaur, Aneet Kamal, Renu Bala, Poonam Kumari, Sumit Sood, and Karan Singh. "Microwave Assisted Vilsmeier-Haack Reaction on Substituted Cyclohexanone Hydrazones: Synthesis of Novel 4,5,6,7-Tetrahydroindazole Derivatives." Letters in Organic Chemistry 16, no. 3 (February 11, 2019): 170–75. http://dx.doi.org/10.2174/1570178615666180917101637.

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Vilsmeier-Haack reaction is one of the most important chemical reactions used for formylation of electron-rich arens. Even though Vilsmeier-Haack reaction was studied on a wide variety of hydrazones of enolizable ketones, literature lacks the examples of the use of 4-substituted cyclohexanones as a substrate. The cyclization potential of hydrazones of cyclic keto compounds is still interested topic of investigation. In the present study, the reaction of various hydrazines with 4-substituted cyclohexanones was proceeded and the resulted hydrazones in crude form were treated with Vilsmeier- Haack reagent using both conventional as well as microwave methods. The reaction of phenyl hydrazine with 4-phenylcyclohexanone yielded the corresponding tetrahydro-1H-carbazole instead of hydrazone during solvent evaporation at 40ºC. By keeping the temperature of water bath to 0ºC, the corresponding hydrazone was isolated in crude form which was immediate treated with POCl3/DMF for 10 min at 90ºC using microwave irradiation method afforded novel 4,5,6,7-tetrahydroindazole derivative. Using this optimized condition, the substrate scope for the synthesis of tetrahydroindazole derivatives was explored and synthesized total 6 final compounds. The microwave assisted synthesis of tetrahydroindazoles from 4-substituted cyclohexanones has been reported for the first time under mild conditions in good yield. Easy work up procedure, high yielding, shortened reaction times, clean and ecofriendly are the main advantages of this protocol.

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Popiołek, Łukasz. "Updated Information on Antimicrobial Activity of Hydrazide–Hydrazones." International Journal of Molecular Sciences 22, no. 17 (August 30, 2021): 9389. http://dx.doi.org/10.3390/ijms22179389.

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Hydrazide–hydrazones possess a wide spectrum of bioactivity, including antibacterial, antitubercular, antifungal, anticancer, anti-inflammatory, anticonvulsant, antidepressant, antiviral, and antiprotozoal properties. This review is focused on the latest scientific reports regarding antibacterial, antimycobacterial, and antifungal activities of hydrazide–hydrazones published between 2017 and 2021. The molecules and their chemical structures presented in this article are the most active derivatives, with discussed activities having a hydrazide–hydrazone moiety as the main scaffold or as a side chain. Presented information constitute a concise summary, which may be used as a practical guide for further design of new molecules with antimicrobial activity.

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Al-Shiekh, Mariam A., Hanady Y. Medrassi, Mohamed H. Elnagdi, and Ebtisam A. Hafez. "Substituted Hydrazonals as Building Blocks in Heterocyclic Synthesis: A New Route to Arylhydrazonocinnolines." Journal of Chemical Research 2007, no. 7 (July 2007): 432–36. http://dx.doi.org/10.3184/030823407x234617.

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2-heteroylhydrazonopropanals 2a–e and 3-oxo-2-arylhydrazonopropanals 2f–k were prepared via coupling of enaminones 1 with aromatic diazonium salts. Compounds 2a–c condensed with hydrazine hydrate to yield the corresponding hydrazones 3a–c which afford on cyclisation the cinnoline derivatives 6a–c, while condensation of 2g, j with hydrazine hydrate directly yielded the pyrazole derivatives 4g–j. Condensation of 2a–c, f, g with phenyl hydrazine gave the corresponding phenyl hydrazone derivatives 7a–c, f, g. Structures of 2a, h and 3a were assessed by single crystal X-ray analyses.

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Edrees, Mastoura M. "Synthesis of 4-hydrazinopyrazolo[3,4-d]pyrimidines and their Reactions with Carbonyl Compounds." Journal of Chemical Research 37, no. 1 (January 2013): 6–10. http://dx.doi.org/10.3184/174751912x13543818811749.

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Synthesis of a new 4-hydrazinopyrazolo[3,4- d]pyrimidine was achieved via heating (4,6-dithioxo-1 H-pyrazolo[3,4- d] pyrimidin-3-yl)acetonitrile with hydrazine hydrate. Reactions of the latter product with thiophene-2-carbaldehyde and ethyl hydrazonoacetoacetate analogues afforded the corresponding hydrazone and pyrazole derivatives, respectively. Similarly, condensation of 2-[6-(benzylsulfanyl)-4-hydrazino-1 H-pyrazolo[3,4- d]pyrimidin-3-yl]acetonitrile with thiophene-2-carbaldehyde and ethyl hydrazonoacetoacetate analogues gave the respective hydrazone and pyrazolone derivatives. Alkylation reactions of 2-[4,6-bis(benzylsulfanyl)-1 H-pyrazolo[3,4- d]pyrimidin-3-yl]acetonitrile with arylamines gave the respective 4-( N-arylamino)-6-benzylsulfanylpyrazolo[3,4- d]pyrimidine derivatives.

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Pogonin, Aleksandr E., George A. Gamov, Maksim N. Zavalishin, and Valentin A. Sharnin. "CONFORMATIONAL BEHAVIOR OF HYDRAZONE DERIVED FROM PYRIDOXAL 5’-PHOSPHATE AND ISONIAZID." IZVESTIYA VYSSHIKH UCHEBNYKH ZAVEDENIY KHIMIYA KHIMICHESKAYA TEKHNOLOGIYA 61, no. 12 (December 12, 2018): 101–7. http://dx.doi.org/10.6060/ivkkt.20186112.5846.

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The hydrazones derived from pyridoxal or pyridoxal 5’-phosphate and heterocyclic hydrazides are of interest due to their potential biological activity and metal sensing properties. These characteristics of hydrazones could be dependent on the conformation equilibria of molecule since the most stable conformer could differ from the one with the highest affinity towards biomolecule or metal ion. In the present contribution, deprotonated hydrazone formed by pyridoxal 5’-phosphate and isoniazid (PLP-INH3-) was studied by means of quantum chemistry. Three rotations leading to eight conformers are possible for this hydrazone; however, four of those species obtained by rotation of pyridine ring of isoniazid residue are degenerated. The geometry of different non-degenerated rotation conformers of the hydrazine (differing by the mutual arrangement of carbonyl group of the isoniazid residue and oxygen in 3’-site of PLP moiety) was optimized using density functional theory (B3LYP/6-311++G(d,p)). Activation barriers were evaluated. Changes in energy and geometry of conformers as well as transition states are discussed. Quantitative QTAIM (Quantum Theory of Atoms in Molecules) analysis was performed in order to check the intermolecular hydrogen bonding existence. The species capable of forming the complex with the metal ions differs from the most stable (according to the total energy values) conformer. The preliminary prediction of biological activity of PLP-INH3- hydrazone and the docking for the hydrazone and G-protein-coupled receptor kinase were performed and the preferable conformation for ligand binding to the kinase active site was found.

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Alheety, Nuaman. "Synthesis, Characterization and Antimicrobial Activity Study of Some New Substituted Benzoxazole Derivatives." Baghdad Science Journal 16, no. 3 (September 1, 2019): 616. http://dx.doi.org/10.21123/bsj.2019.16.3.616.

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This research included the preparation of 2-mercaptobenzoxazole (N1) by the reaction of ortho-aminophenol with carbon disulfide in an alcoholic potassium hydroxide solution. The 2-mercapto benzoxazole (N1) was then treated with hydrazine to obtain the 2-hydrazino benzoxazole (N2). A number of hydrazones (N3-N5) were prepared through the reaction of N2 with different benzaldehydes. The compound (N6) was also prepared whereby the ring closing of hydrazone (N3) using chloroacetylchloride, while the compound (N7) was prepared by treating 2-hydrazino benzoxazole with acetylacetone. When the compound (N1) was treated with formaldehyde, it afforded the compound (N8). Also, the N9 was obtained from the reaction of N1 with chloroacetic acid in the presence of alcoholic potassium hydroxide. The prepared compounds were characterized using physico-chemical and spectroscopic methods such as melting point, infrared spectroscopy (IR) and the proton nuclear magnetic resonance (1H-NMR). Thereafter, some of the compounds were selected for in vitro antibacterial activity and one of these compounds showed an inhibition effect against gram positive only which is very important because it is considered as specific antibacterial drug.

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7

Groziak, Michael P., and Paul D. Robinson. "The Structural Basis for Hydrolysis Resistance in the Esters of (2-Formylphenyl)boronic Acid 2,4-Dinitrophenylhydrazones." Collection of Czechoslovak Chemical Communications 67, no. 7 (2002): 1084–94. http://dx.doi.org/10.1135/cccc20021084.

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Under conditions that typically afford bicyclic boron heterocycles directly, (2-formylphenyl)boronic acids react with 2,4-dinitrophenylhydrazine in ethanol to give highly waterresistant diethyl boronate esters. Two such 2,4-dinitrophenylhydrazones were prepared and their X-ray crystal structures determined. Contrary to a previous suggestion that their unusual stability is due to an intramolecular N→B coordination giving a six-membered BN2C3 ring system based on a (Z)-hydrazone, these compounds instead were found to be (E)-hydrazones internally stabilized by a weak intramolecular interaction between nitrogen and boron from within a five-membered ring. Further study revealed that the electron deficiency of the starting hydrazine reagent plays a key role in determining the structure of the hydrazone isolated, and that the water-resistant boronate esters can be hydrolyzed under forcing conditions to the boronic acids.

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Ünver, Hakan, Burak Berber, Rasime Demirel, and Ayşe T. Koparal. "Design, Synthesis, Anti-Proliferative, Anti-microbial, Anti-Angiogenic Activity and In Silico Analysis of Novel Hydrazone Derivatives." Anti-Cancer Agents in Medicinal Chemistry 19, no. 13 (December 11, 2019): 1658–69. http://dx.doi.org/10.2174/1871520619666190318125824.

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Background: Cancer is the second leading cause of death globally. Hydrazone and hydrazone derivatives have high activity, and for this reason, these compound are greatly used by researchers to synthesize new anti-cancer drug. The aim of this research work is to synthesize novel anticancer agents. Methods: New hydrazone derivatives were synthesized via a reaction between 3-formylphenyl methyl carbonate and benzhydrazide, 4-methylbenzoic hydrazide, 4-tert-butylbenzoic hydrazide, 4-nitrobenzoic hydrazide and 3- methoxybenzoic hydrazide, and were successfully characterized using elemental analysis, 1H-NMR, 13C-NMR, FT-IR and LC-MS techniques. The synthesized compounds were evaluated for their antimicrobial (some grampositive and -negative bacteria, filamentous fungi and yeasts), anti-proliferative (T47D and HCC1428-breast cancer cells) and anti-angiogenic (HUVEC-endothelial cells) activities. The anti-proliferative activities of the hydrazone compounds R1-R5 were studied on these cell lines by MTT assay. The anti-angiogenic potential of the compounds was determined by the endothelial tube formation assay. To identify structural features related to the anti-proliferative activity of these compounds, 2D-QSAR was performed. Results: The results indicated that compound R3 exhibited strong anti-angiogenic and anti-proliferative activity on breast cancer cell lines and healthy cell lines. Also, this compound; possessing a tertiary butyl moiety on the hydrazine, exhibited the highest inhibitory effect against all tested microorganisms; in particular, it inhibited Candida albicans at a lower concentration than ketoconazole. Among the investigated compounds, those bearing methyl, tertiary butyl (compound R2, R3) and methoxy (compound R5) moiety were found to be more successful anticandidal derivatives than standard antifungal antibiotics. The QSAR analysis suggested that the tumor specificity of the hydrazone correlated with their molecular weight, lipophilicity, molar refractivity, water solubility, DipolHybrid:(MOPAC) and ExchangeEnergy:(MOPAC). Absorption, Distribution, Metabolism and Elimination (ADME) analysis of the hydrazone compounds showed that they have favorable pharmacokinetic and drug-likeness properties. The ADME results clarify that R3 is the best compound in terms of pharmacokinetic properties. In contrast to other compounds; target prediction analysis of the compound R3 showed inhibitory activity on estrogen-related receptor alpha transcription factor (ESRRA). The target prediction analysis was supported by molinspiration bioactivity score. Conclusion: The R3 compound is considered to be an important candidate for future studies with its suitability for the Lipinski’s rule of five for drug-likeness, and effective in vitro and in silico results.

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Jasril, E. Juwiyatri, S. N. Fauza, and N. Afriana. "Synthesis, in vitro Antioxidant Activity, and Toxicity Evaluation of Hydrazone Derivatives Naphthalene-1-ylmethylene hydrazine." Journal of Physics: Conference Series 2049, no. 1 (October 1, 2021): 012050. http://dx.doi.org/10.1088/1742-6596/2049/1/012050.

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Abstract Hydrazone is a versatile organic compound that has a basic structure (-NHN=CH-) called the azomethine group. This structure is responsible for the physical and chemical of hydrazone, which makes this compound has variety bioactivities such as antioxidant, antitumor, and anticancer. In this work, two hydrazone derivatives from 1-naphthaldehyde and hydrazine (phenylhydrazine/hydrazine hydrate) have been synthesized under microwave irradiation. Their antioxidant activity and toxicity were evaluated by DPPH and BSLT method, respectively. Structures of the synthesized compounds were confirmed based on spectroscopic data included UV, FTIR, HRMS, and 1H-NMR. Based on the DPPH assay, hydrazone from phenylhydrazine has strong antioxidant (IC50 28.90 μg/mL) but inactive antioxidant for hydrazine hydrate (IC50 >1000 μg/mL). However, both compounds have a high toxicity effect on Artemia Salina Leach with each LC50 1.45 and 47.20 μg/mL, hence they have the potential to be developed into anticancer drugs.

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10

Wu, Shouting, Xi Liang, Fang Luo, Hua Liu, Lingyi Shen, Xianjiong Yang, Yali Huang, et al. "Synthesis, Crystal Structure and Bioactivity of Phenazine-1-carboxylic Acylhydrazone Derivatives." Molecules 26, no. 17 (September 1, 2021): 5320. http://dx.doi.org/10.3390/molecules26175320.

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A phenazine-1-carboxylic acid intermediate was synthesized from the reaction of aniline and 2-bromo-3-nitro-benzoic acid. It was then esterified and reacted with hydrazine hydrate to afford phenazine-1-carboxylic hydrazine. Finally, 10 new hydrazone compounds 3a–3j were obtained by the condensation reaction of phenazine-1-carboxylic acid hydrazide and the respective aldehyde-containing compound. The structures were characterized by 1H and 13C NMR spectroscopy, MS and single crystal X-ray diffraction. The antitumor activity of the target compounds in vitro (HeLa and A549) was determined by thiazolyl blue tetrazolium bromide. The results showed that compound (E)-N′-(2-hydroxy-4-(2-(piperidine-1-yl) ethoxy) benzyl) phenazine-1-carbonyl hydrazide 3d exhibited good cytotoxic activity.

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Fatullayeva, P. A. "COMPLEXES OF METALS WITH HYDRAZONE HYDRAZIDE SALICYLIC ACID." Chemical Problems 19, no. 2 (2021): 79–83. http://dx.doi.org/10.32737/2221-8688-2021-2-79-83.

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Complexes of Cu (II), Ni (II), and Co (II) with hydrazone derivatives of salicylic acid hydrazide and 3,5-di-tert-butyl salicylic aldehyde (LH) were synthesized and the structure of these compounds studied by means of elemental analysis methods, IR and electronic spectroscopy, magnetochemistry and thermal analysis. It revealed that the complexes are monomeric and have a composition [MLXSoI] where M is a metal ion, L is a ligand, X is an inorganic anion, and Sol is a solvent molecule. LH- in the complexes behaves like a monoanionic tridentate ligand. It found that the resulting complexes exhibit noticeable inhibitory and urease activity.

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12

KushalNath Mishra, Shambaditya Goswami, Kumudhavalli M.V, Kamal Saini, Nikita Pal, Nilesh Sharma, and Pragya Pandey. "Hydrazones and their metal complexes: A short review on their biological potentia." International Journal of Research in Pharmaceutical Sciences 11, SPL4 (December 21, 2020): 1440–47. http://dx.doi.org/10.26452/ijrps.v11ispl4.4319.

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Hydrazones belong to complexes are beneficial in different fields for their essential role in the development of a range of stable complexes in the coordination chemistry. Different researchers have reported the various medicinal properties of hydrazones. Hydrazone and its metal complexes are useful for the detection of some organic components from pharmaceutical formulations. These metallic compounds act as a catalyst for conducting various chemical reactions and help in making different chemical complexes that are effective against bacteria, fungi, and many other microbes. Aromatic hydrazone derivatives can measure the concentration of low molecular weight aldehyde and ketone complexes. Hydrazones possess numerous medicinal properties, including antimicrobial, anti-cancer, antidepressant, anti-tubercular, anti-viral, etc. For the new drug discovery, hydrazones/azomethines are considered to be an important class of compound. From molecular biology to pharmaceutical formulation, organic chemistry, new drug development process, the importance of hydrazone and its metal complexes is immense. The present review aims to highlight the reported biological activities related to hydrazones for the last decade.

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Kalaiarasi, N., and S. Manivarman. "Spectral characterization, microbial activities and toxicity study of some newly synthesized hydrazone derivatives." International Journal of Advanced Chemistry 5, no. 2 (June 22, 2017): 54. http://dx.doi.org/10.14419/ijac.v5i2.7739.

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Hydrazone derivatives of 2-Thioxodihyropyrimidine-2-dione were synthesized by addition of thiobarbituric acid with phenyl hydrazine, dinitrophenyl hydrazine, semicarbazide, thiosemicarbazide and benzohydrazide respectively. Structures of these synthesized compounds are characterized by means of UV, IR, Proton-NMR, Carbon- NMR. Finally the hydrazone derivatives synthesized are screened for biological activities namely antibacterial and antifungal activities. Also in addition the toxicity studies of the compounds are also performed.

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Gavara, Laurent, Federica Verdirosa, Alice Legru, Paola Sandra Mercuri, Lionel Nauton, Laurent Sevaille, Georges Feller, et al. "4-(N-Alkyl- and -Acyl-amino)-1,2,4-triazole-3-thione Analogs as Metallo-β-Lactamase Inhibitors: Impact of 4-Linker on Potency and Spectrum of Inhibition." Biomolecules 10, no. 8 (July 23, 2020): 1094. http://dx.doi.org/10.3390/biom10081094.

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To fight the increasingly worrying bacterial resistance to antibiotics, the discovery and development of new therapeutics is urgently needed. Here, we report on a new series of 1,2,4-triazole-3-thione compounds as inhibitors of metallo-β-lactamases (MBLs), which represent major resistance determinants to β-lactams, and especially carbapenems, in Gram-negative bacteria. These molecules are stable analogs of 4-amino-1,2,4-triazole-derived Schiff bases, where the hydrazone-like bond has been reduced (hydrazine series) or the 4-amino group has been acylated (hydrazide series); the synthesis and physicochemical properties thereof are described. The inhibitory potency was determined on the most clinically relevant acquired MBLs (IMP-, VIM-, and NDM-types subclass B1 MBLs). When compared with the previously reported hydrazone series, hydrazine but not hydrazide analogs showed similarly potent inhibitory activity on VIM-type enzymes, especially VIM-2 and VIM-4, with Ki values in the micromolar to submicromolar range. One of these showed broad-spectrum inhibition as it also significantly inhibited VIM-1 and NDM-1. Restoration of β-lactam activity in microbiological assays was observed for one selected compound. Finally, the binding to the VIM-2 active site was evaluated by isothermal titration calorimetry and a modeling study explored the effect of the linker structure on the mode of binding with this MBL.

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Asif, Mohammad, and Asif Husain. "Analgesic, Anti-Inflammatory, and Antiplatelet Profile of Hydrazones Containing Synthetic Molecules." Journal of Applied Chemistry 2013 (December 17, 2013): 1–7. http://dx.doi.org/10.1155/2013/247203.

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Hydrazones are present in many of the bioactive compounds with wide interest because of their diverse pharmacological applications. Hydrazones possess wide variety of biological activities such as anticonvulsant, antidepressant, analgesic, anti-inflammatory, antiplatelet, antimicrobial, anticancer, antihypertensive, anthelmintic, antidiabetic, antiparasitic, and other anticipated activities. This created an interest for researchers towards synthesized variety of hydrazone derivatives for different biological activities. Therefore many researchers have synthesized hydrazone derivatives as target structures for their biological activities. This is paper focuses on the analgesic, anti-inflammatory, and antiplatelet activities of hydrazones.

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Ristić, Milenko, Biljana Dekić, Niko Radulović, and Marija Aksić. "Synthesis, complete assignment of 1H- and 13C-NMR spectra and antioxidant activity of new azine derivative bearing coumarin moiety." Bulletin of Natural Sciences Research 11, no. 1 (2021): 9–16. http://dx.doi.org/10.5937/bnsr11-31265.

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In this research, the synthesis of a new azine derivative with coumarin moiety was performed in three reaction steps, starting from 4-hydroxycoumarin. The first step in synthesis was the acetylation of 4-hydroxycoumarin to yield 3-acetyl-4-hydroxycoumarin and then the obtained 3-acetyl-4-hydroxycoumarin was reacted with hydrazine hydrate and give a corresponding hydrazone. Condensation of the hydrazone with 4-ethoxy-3methoxybenzaldehyde afforded the target compound 1-[1-(4-hydroxy-2-oxo-2H-chromen-3-yl)-ethylidene]-2-(4etoxy-3-methoxybenzylidene)-hydrazine in a good yield. The resulting azine derivative is fully spectrally characterized, including complete assignment of 1Hand 13C-NMR spectra, as well as 2D NMR (1H1H COSY, NOESY, HSQC and HMBC) spectra. The antioxidant activity of corresponding hydrazone and target compound was evaluated by DPPH method where hydrazone derivative displayed a significant and target azine good antioxidant activity, with IC50 (mM) values 11.69 and 216.60, respectively.

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Gera, Ankur, Chander Mohan, and Sandeep Arora. "Synthesis of Phthaloylglycyl Hydrazide Derivatives: Selective Protection of Phthalimide Group from Hydrazinolysis." Current Organic Synthesis 15, no. 6 (August 29, 2018): 839–45. http://dx.doi.org/10.2174/1570179415666180601083256.

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Background: N-phthalimide amino acid hydrazide is a class of compounds that have the potential therapeutic use. In general, hydrazinolysis of N-substituted amino acid(s) ester removes the ester group and yields the corresponding hydrazide. However, in case if N-substitution group is phthalimide, phthalimide group is cleaved and not the ester group. The resulted compound, therefore, is amino acid ester rather than Nphthalimide amino acid hydrazide. The above class of compounds, because of susceptibility of phthalimide group to hydrazinolysis, has previously been synthesized by a lengthy three-step procedure. Objective: N-phthaloylglycyl hydrazide was synthesized by using new efficient, simplified, one step process. Hydrazone derivatives from substituted benzaldehydes, and substituted furaldehyde were also synthesized. Method: N-phthaloylglycyl hydrazide was synthesized from the corresponding carboxylic acid using 1-Ethyl- 3-(3-dimethylaminopropyl)carbodiimide (EDC) as a coupling agent and hydroxybenzotriazole (HOBt) as an activator. Hydrazone derivatives were synthesized by condensation of N-phthaloylglycyl hydrazide with substituted benzaldehyde/substituted furaldehydes. All the compounds were characterized by IR, 1H-NMR, 13CNMR, mass spectroscopy and elemental analysis. Results: The presence of EDC/HOBt resulted in hydrazinolysis of the carboxylic acid group and not the phthalimide group. N-phthaloylglycyl hydrazide was synthesized in good yield. Conclusion: We report the improved process of the synthesis of N-phthaloylglycyl hydrazide. This is the first report where stability of phthaloyl amino acid compound to hydrazine is demonstrated. The reaction may be explored for the reaction schemes where stability of phthalimide group to hydrazinolysis is required.

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Li, Chao-Jun, Jianlin Huang, Xi-Jie Dai, Haining Wang, Ning Chen, Wei Wei, Huiying Zeng, et al. "An Old Dog with New Tricks: Enjoin Wolff–Kishner Reduction for Alcohol Deoxygenation and C–C Bond Formations." Synlett 30, no. 13 (June 13, 2019): 1508–24. http://dx.doi.org/10.1055/s-0037-1611853.

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The Wolff–Kishner reduction, discovered in the early 1910s, is a fundamental and effective tool to convert carbonyls into methylenes via deoxygenation under strongly basic conditions. For over a century, numerous valuable chemical products have been synthesized by this classical method. The reaction proceeds via the reversible formation of hydrazone followed by deprotonation with the strong base to give an N-anionic intermediate, which affords the deoxygenation product upon denitrogenation and protonation. By examining the mechanistic pathway of this century old classical carbonyl deoxygenation, we envisioned and subsequently developed two unprecedented new types of chemical transformations: a) alcohol deoxygenation and b) C–C bond formations with various electrophiles including Grignard-type reaction, conjugate addition, olefination, and diverse cross-coupling reactions.1 Introduction2 Background3 Alcohol Deoxygenation3.1 Ir-Catalyzed Alcohol Deoxygenation3.2 Ru-Catalyzed Alcohol Deoxygenation3.3 Mn-Catalyzed Alcohol Deoxygenation4 Grignard-Type Reactions4.1 Ru-Catalyzed Addition of Hydrazones with Aldehydes and Ketones4.2 Ru-Catalyzed Addition of Hydrazone with Imines4.3 Ru-Catalyzed Addition of Hydrazone with CO2 4.4 Fe-Catalyzed Addition of Hydrazones5 Conjugate Addition Reactions5.1 Ru-Catalyzed Conjugate Addition Reactions5.2 Fe-Catalyzed Conjugate Addition Reactions6 Cross-Coupling Reactions6.1 Ni-Catalyzed Negishi-type Coupling6.2 Pd-Catalyzed Tsuji–Trost Alkylation Reaction7 Other Reactions7.1 Olefination7.2 Heck-Type Reaction7.3 Ullmann-Type Reaction8 Conclusion and Outlook

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Krátký, Martin, Katarína Svrčková, Quynh Anh Vu, Šárka Štěpánková, and Jarmila Vinšová. "Hydrazones of 4-(Trifluoromethyl)benzohydrazide as New Inhibitors of Acetyl- and Butyrylcholinesterase." Molecules 26, no. 4 (February 13, 2021): 989. http://dx.doi.org/10.3390/molecules26040989.

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Based on the broad spectrum of biological activity of hydrazide–hydrazones, trifluoromethyl compounds, and clinical usage of cholinesterase inhibitors, we investigated hydrazones obtained from 4-(trifluoromethyl)benzohydrazide and various benzaldehydes or aliphatic ketones as potential inhibitors of acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE). They were evaluated using Ellman’s spectrophotometric method. The hydrazide–hydrazones produced a dual inhibition of both cholinesterase enzymes with IC50 values of 46.8–137.7 µM and 19.1–881.1 µM for AChE and BuChE, respectively. The majority of the compounds were stronger inhibitors of AChE; four of them (2-bromobenzaldehyde, 3-(trifluoromethyl)benzaldehyde, cyclohexanone, and camphor-based 2o, 2p, 3c, and 3d, respectively) produced a balanced inhibition of the enzymes and only 2-chloro/trifluoromethyl benzylidene derivatives 2d and 2q were found to be more potent inhibitors of BuChE. 4-(Trifluoromethyl)-N’-[4-(trifluoromethyl)benzylidene]benzohydrazide 2l produced the strongest inhibition of AChE via mixed-type inhibition determined experimentally. Structure–activity relationships were identified. The compounds fit physicochemical space for targeting central nervous systems with no apparent cytotoxicity for eukaryotic cell line together. The study provides new insights into this CF3-hydrazide–hydrazone scaffold.

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Abdelmohsen, Shawkat A., and Talaat I. El Emary. "SYNTHESIS, CHARACTERIZATION AND ANTIMICROBIAL ACTIVITY OF NOVEL PYRAZOLO[3,4-b]PYRIDINES AND THEIR SPIRO-HETEROCYCLIC DERIVATIVES." JOURNAL OF ADVANCES IN CHEMISTRY 10, no. 7 (January 22, 2014): 2901–15. http://dx.doi.org/10.24297/jac.v10i7.6802.

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The present work describes the synthesis of a novel series of heterocyclic moieties derived from 5-acetylpyrazolo[3,4-b]pyridine (1). The formation of chalcones (2a-d) was utilized to synthesize pyrazoline, isoxazoline and pyrimidine derivatives (3-10). Thiosemicarbazone and semicarbazone (11, 17) were utilized to synthesize other new triazolethiones, thiadiazole and selenadiazole derivatives (11-19). Some new spiro derivatives (22-25) were synthesized by the reaction of chalcone (21) of 1 and isatine with hydrazines, hydroxyl amines and thiourea. Also, The reaction of 1 with cyanoacetyl hydrazine gave the hydrazide-hydrazone derivative 26, which was allowed to react with aromatic aldehydes and α-cyanocinnamonitrile to afford coumarine and substituted pyridine derivatives (28, 29). The structures of all the new compounds have been established on the basis of their analytical and spectral data. Twenty two of the synthesized compounds were also evaluated for their antibacterial and antifungal activity against various strains of bacteria and fungi and most are found to possess promising antimicrobial activity when compared with Chloramphenicol and Clotrimazole

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Ji, Heng, Hui-qiong Ni, Peng Zhi, Zi-wei Xi, Wei Wang, Jian-jun Shi, and Yong-miao Shen. "Visible-light mediated directed perfluoroalkylation of hydrazones." Organic & Biomolecular Chemistry 15, no. 28 (2017): 6014–23. http://dx.doi.org/10.1039/c7ob01144j.

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A convenient and efficient protocol was reported to access a series of perfluoroalkylated aromatic aldehyde hydrazones. Aliphatic aldehyde hydrazones and N-monosubstituted hydrazones which are unreactive in previously reported hydrazone perfluoroalkylation reactions now take part in the reaction.

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22

Hamed, Atef A., Hesham F. Bader, and El-Sayed H. El-Ashry. "4′, x-Seco And 4′,x-4′,5′-Diseco C-Nucleosides From 2-Hydrazino-(3H)- Thieno [2,3-D] Pyrimidin-4-Ones." Zeitschrift für Naturforschung B 56, no. 8 (August 1, 2001): 826–36. http://dx.doi.org/10.1515/znb-2001-0817.

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Cyclization of 2-hydrazino-5,6-dimethyl-3H-thieno[2,3-d]pyrimidin-4-one (1) with acetic acid gave 3,6,7-trimethyl-l,2,4-triazolo[3,4-a]thieno[2,3-d] pyrimidin-5-one (5) whose Dimroth rearrangement gave 2,6,7-trimethyl-l,2,4-triazolo[3,4-a]thieno[2,3-d]pyrimidin-5-one (11). Alternatively, 5 was obtained from the dehydrogenative cyclization of acetaldehyde 5,6- dimethyl-4-3H-oxo-thieno[2,3-d]pyrimidin-2-yl hydrazone (7). Reaction of 1 and 2 with a number of sugars gave the respective hydrazones 19 and 20. Those of the D-glucose exist in the cyclic pyranosyl structure in addition to minor amounts of the acyclic structure. Dehydrogenative cyclization of the sugar hydrazones gave the respective fused tricyclic compounds 25 and 26

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23

Chandrasekhar, Vadapalli, Venkatasubbaiah Krishnan, Arunachalampillai Athimoolam, and Gurusamy Thangavelu Senthil Andavan. "New hybrid inorganic-organic polymers containing cyclophosphazenes as pendant groups: Cyclophosphazene ligands containing hydrazone linkages and their conversion to polymers." Canadian Journal of Chemistry 80, no. 11 (November 1, 2002): 1415–20. http://dx.doi.org/10.1139/v02-099.

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The reaction of the cyclotriphosphazene N3P3Cl5[O-C6H4-p-C6H4-p-CH=CH2] (2) with 10 equiv of N-methylhydrazine proceeds in a regio-specific manner to afford the multi-functional hydrazide N3P3[N(Me)NH2]5[O- C6H4-p-C6H4-p-CH=CH2] (3). Condensation of 3 with o-hydroxy benzaldehyde or pyridine-2-carboxaldehyde affords the corresponding hydrazones N3P3[N(Me)N=CH-C6H4-o-OH]5[O-C6H4-p-C6H4-p-CH=CH2] (4) and N3P3[N(Me)N=CH-C6H4N]5[O-C6H4-p-C6H4-p-CH=CH2] (5), respectively. These hydrazones can be homopolymerized to afford polymers 6 and 7 containing multi-site coordinating cyclophosphazenes as pendant groups.Key words: cyclophosphazene, hydrazone, pendant polymers, hybrid polymers, polymeric ligands.

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24

Hishmat, O. H., S. S. Mabrouk, A. M. M. Nasef, N. M. A. Shayeb, and S. A. Ismail. "Derivatives of Khellinonequinone and their Aflatoxigenic Activity." Zeitschrift für Naturforschung B 43, no. 3 (March 1, 1988): 343–46. http://dx.doi.org/10.1515/znb-1988-0318.

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Nitration of khellinone leads to the formation of a small amount of 3-nitrokhellinone and 5-acetyl-6-hydroxybenzofuran-4.7-dione (khellinonequinone) as a main product. The latter compound reacts with primary amines to give the corresponding imino compounds. Reaction of khellinone with o-phenylenediamine involves condensation followed by cyclisation. While on the other hand treating with phenyl hydrazines gives the phenyl hydrazone. The pyrazolobenzofuran derivative was obtained by the action of hydrazine hydrate on khellinonequinone. Finally the reaction with malononitrile leads to the formation of the ylidene derivative. Two quinone derivatives showed a weak effect on mycelial growth and aflatoxin formation.

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25

Hajipour, Abdol Reza, Iraj Mohammadpoor-Baltork, and Mansour Bigdeli. "A Convenient and Mild Procedure for the Synthesis of Hydrazones and Semicarbazones from Aldehydes or Ketones under Solvent-free Conditions." Journal of Chemical Research 23, no. 9 (September 1999): 570–71. http://dx.doi.org/10.1177/174751989902300926.

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26

Pisk, Jana, Ivica Đilović, Tomica Hrenar, Danijela Cvijanović, Gordana Pavlović, and Višnja Vrdoljak. "Effective methods for the synthesis of hydrazones, quinazolines, and Schiff bases: reaction monitoring using a chemometric approach." RSC Advances 10, no. 63 (2020): 38566–77. http://dx.doi.org/10.1039/d0ra06845d.

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27

Patra, Debashis, Subhabrata Paul, Indira Majumder, Nayim Sepay, Sachinath Bera, Rita Kundu, Michael G. B. Drew, and Tapas Ghosh. "Exploring the effect of substituent in the hydrazone ligand of a family of μ-oxidodivanadium(v) hydrazone complexes on structure, DNA binding and anticancer activity." Dalton Transactions 46, no. 46 (2017): 16276–93. http://dx.doi.org/10.1039/c7dt03585c.

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28

Hrnčiar, Pavel, and Eva Švanygová. "Reactions of 2-Acyl-1,3-indandiones with Nitrogen Nucleophiles." Collection of Czechoslovak Chemical Communications 59, no. 12 (1994): 2734–40. http://dx.doi.org/10.1135/cccc19942734.

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Reactions of 2-acyl-1,3-indandiones with nitrogen nucleophiles were studied rarely. The question, if they react with carbonyl carbon of acyl group or indandione skeleton, has not been answered unambiguously. To make clear the question which carbonyl carbon of 2-acyl-1,3-indandiones enters the reaction with nitrogen nucleophiles we carried out the reactions with 2-acetyl- (Ia), 2-propionyl- (Ib), 2-pivaloyl- (Ic), and 2-benzoyl-1,3-indandione (Id). We used different 2-acyl-1,3-indandiones with the aim to find out if the character of acyl group affects the course of reaction. We used ethoxyamine, primary amines, phenylhydrazine, hydrazine and methylhydrazine as nucleophile reactants. The reactions were carried out in methanol at reflux at 10% excess of nitrogen base. The reactions with phenylhydrazine, hydrazine and methylhydrazine were performed with twofold excess of nitrogen base. The separation of reaction products was carried out by chromatography on silica gel. We found that 2-acyl-1,3-indandiones I react with ethoxyamine both at the acylcarbonyl carbon to produce 2-(1-ethoxyiminoalkyl)-1,3-indandiones II and the carbonyl carbon of indandione skeleton to give rise 3-(ethoxyimino)-2-acyl-1-indanones III. In all cases, the carbonyl carbon of acyl group was preferred (the observed ratio of products II to III was 6 - 8 : 1). From the reaction of 2-acyl-1,3-indandiones with primary amines only the products IV of reaction with the acylcarbonyl carbon were isolated. The hydrazines used reacted with 2-acyl-1,3-indandiones also at carbonyl carbon of acyl group in the first step to produce hydrazones. However, the products isolated in most cases were formed by the attack of hydrazone nitrogen at carbonyl carbon of indandione skeleton giving rise to derivatives of indeno[2,3-d]pyrazole-4-one V. It is interesting that 2-acetyl-1,3-indandione and 2-propionyl-1,3-indandione, reacting with phenylhydrazine and hydrazine, yielded only corresponding hydrazones VI.

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29

Abidov, Musa T. "Pharmacological aspects of hydrazides and hydrazide derivatives." Health Promotion & Physical Activity 2, no. 3 (June 30, 2017): 9–21. http://dx.doi.org/10.5604/01.3001.0010.7718.

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Intense search for new antimicrobials, including anti-tuberculosis drugs, is dictated by the phenomenon of bacterial multidrug resistance. Hydrazides are considered the key intermediate and valuable starting material for some novel biologically active compounds. Over 70% of recently reported synthetic hydrazide derivatives are evaluated for antimicrobial and/or antifungal activity. The most frequently applied hydrazide is an anti- tuberculosis drug isoniazid/isonicotinic acid hydrazide (NIH). Hydrazide chemicals are sharing a common functional group characterized by a nitrogen- to-nitrogen covalent bond with four substituents with at least one of them being an acyl group, whereas the related hydrazines do not carry an acyl group. Hydrazides can be further classified by atom attached to the oxygen: carbohydrazides, sulfonohydrazides, phosphonic dihydrazides, hydrazone-hydrazides and phthalhydrazides. In addition to their antibacterial and antifungal activities, hydrazide derivatives have recently attracted continuing interest because of their anti-inflammatory properties. A phthalhydrazide derivative tamerit/galavit has been successfully introduced for human therapies.

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30

Ain, Noor ul, Tariq Mahmood Ansari, M. Rehan H. Shah Gilani, Guobao Xu, Gaolin Liang, Rafael Luque, Mabkhoot Alsaiari, and Mohammed Jalalah. "Facile and straightforward synthesis of Hydrazone derivatives." Journal of Nanomaterials 2022 (March 11, 2022): 1–6. http://dx.doi.org/10.1155/2022/3945810.

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This study was undertaken to report the swift, facile and convenient synthesis of novel hydrazones obtained by condensation reaction between 2-Amino-3-formylchromone and hydrazine derivatives. Various characterization techniques such as MALDI Mass, FTIR, 1HNMR and 13CNMR spectrum analysis was done to determine the chemical structure of these novel six hydrazones. Furthermore, UV-Vis and fluorescence spectra was studied to calculate λmax and εmax. These hydrazones are quite useful for their facile synthesis and chemical structure. Such hydrazones require separate clinical research to find their applications in biomedical fields.

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31

Dinda, Soumitra, Tamanna Sultana, Suhana Sultana, Sarat Chandra Patra, Arup Kumar Mitra, Subhadip Roy, Kausikisankar Pramanik, and Sanjib Ganguly. "Ruthenocycles of benzothiazolyl and pyridyl hydrazones with ancillary PAHs: synthesis, structure, electrochemistry and antimicrobial activity." New Journal of Chemistry 44, no. 26 (2020): 11022–34. http://dx.doi.org/10.1039/d0nj01447h.

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The antimicrobial activity of ruthenocycles of pyridyl and benzothiazolyl hydrazones has been investigated. The study established that such activity is comparatively higher for the complex containing benzothiazolyl hydrazone.

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32

Dammene Debbih, Ouafa, Assia Sid, Rafika Bouchene, Sofiane Bouacida, Wissam Mazouz, and Noureddine Gherraf. "Two hydrazones derived from 1-aryl-3-(p-substituted phenyl)prop-2-en-1-one: synthesis, crystal structure, Hirshfeld surface analysis andin vitrobiological properties." Acta Crystallographica Section C Structural Chemistry 74, no. 6 (May 22, 2018): 703–14. http://dx.doi.org/10.1107/s2053229618006812.

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Two chalcones were synthesized by the aldolic condensation of enolizable aromatic ketones with substituted benzaldehydes under Claisen–Schmidt reaction conditions and then treated with 2,4-dinitrophenylhydrazine to yield their corresponding hydrazones. The two (E,Z)-2,4-dinitrophenylhydrazone structures, namely (Z)-1-(2,4-dinitrophenyl)-2-[(E)-3-(4-methylphenyl)-1-phenylallylidene]hydrazine, C22H18N4O4, (H1), and (Z)-1-[(E)-3-(4-chlorophenyl)-1-(naphthalen-1-yl)allylidene]-2-(2,4-dinitrophenyl)hydrazine, C25H17ClN4O4, (H2), were isolated by recrystallization and characterized by FT–IR, UV–Vis, single-crystal and powder X-ray diffraction methods. The UV–Vis spectra of the hydrazones have been studied in two organic solvents of different polarity. It was found that (H2) has a molar extinction coefficient larger than 40000. Single-crystal X-ray diffraction analysis reveals that the molecular zigzag chains of (H1) and (H2) are interconnected through noncovalent contacts. A quantitative analysis of the intermolecular interactions in the crystal structures has been performed using Hirshfeld surface analysis. All the synthesized chalcones and hydrazones were evaluated for their antibacterial and antioxidant activities. Results indicate that the studied compounds show significant activity against Gram negativeEscherichia colistrain and the chalcone 3-(4-methylphenyl)-1-phenylprop-2-en-1-one, (C1), was the most effective. In addition, only hydrazone (H1) displayed a moderate DPPH (2,2-diphenyl-1-picryl hydrazyl) scavenging efficiency.

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33

Abo-Ghalia, Mohamed H., Abd El-Galil E. Amr, and Mohamed M. Abdalah. "Synthesis of Some New (Nα-Dipicolinoyl)-bis-L-leucyl-DL-norvalyl Linear tetra and Cyclic octa Bridged Peptides as New Antiinflammatory Agents." Zeitschrift für Naturforschung B 58, no. 9 (September 1, 2003): 903–10. http://dx.doi.org/10.1515/znb-2003-0912.

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In continuation to our search for new amino acid and peptide based anti-inflammatory agents, the suggestion, synthesis, structure elucidation of some Nα -bis-dipicolinoyl amino acids, linear tetra and cyclic octa bridged peptides 1-9, of which four are new compounds 6-9, were herein realized. Accordingly, Nα -bis-dipicolinoyl-L-leucine methyl ester 1, the corresponding acid 2, its bis-DL-norvalyl methyl ester homologue 3, the acid 4 and hydrazide 5 analogues were conventionally prepared.The tetrachlorophthalic acid hydrazine conjugate 6, anisaldehyde hydrazone 7, the benzenetetracarboxylic acid and naphthalenetetracarboxylic acid bis-L-leucyl-DL-norvalyl cyclic octa bridged peptides 8 and 9 respectively, were newly synthesized via condensation of the hydrazide 5 with the corresponding aldehyde or anhydride.The chromatographic, IR, NMR and mass spectral analysis confirmed the identities of the synthesized compounds.Comparable to the two reference antiinflammatory drugs indomethacin® and voltaren® (100%), the determined antiinflammatory potency of the candidates (carrageenan® induced paw edema in rats) revealed a general significant activity (66 - 94%), except for the practically inactive 6 (∼1.5 % activity).In particular, the potency of the (Nα -dipicolinoyl)-bis-L-leucyl-DL-norvalyl anisaldehyde hydrazone 7 was of 94 and 87%, comparable to the reference drugs. However, 7 also showed 58% protection against ulcer formation, comparable to null for indomethacin®. Additionally, an acceptable acute toxicity was observed (LD50: 2833 mg/kg, comparable to 2700 and 2850 for indomethacin® and voltaren® respectively).

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34

Dilek, Ozlem, Zhen Lei, Kamalika Mukherjee, and Susan Bane. "Rapid formation of a stable boron–nitrogen heterocycle in dilute, neutral aqueous solution for bioorthogonal coupling reactions." Chemical Communications 51, no. 95 (2015): 16992–95. http://dx.doi.org/10.1039/c5cc07453c.

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Reaction of 2-formylphenylboronic acid with an aromatic hydrazine does not product the expected hydrazone, but rather a boron-containing aromatic heterocycle. The characteristics of the reaction are highly desirable for bioconjugations.

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35

Wu, Jiale, Jiafeng Wang, Yinglong Han, Yu Lin, Jing Wang, and Ming Bu. "Synthesis and Cytotoxic Activity of Novel Betulin Derivatives Containing Hydrazide-Hydrazone Moieties." Natural Product Communications 16, no. 10 (October 2021): 1934578X2110553. http://dx.doi.org/10.1177/1934578x211055345.

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A series of novel betulin derivatives containing hydrazide-hydrazone moieties were synthesized. All compounds were evaluated for their cytotoxicity against four human carcinoma cell lines (HepG2, A549, MCF-7 and HCT-116) and a normal human gastric epithelial cell line (GES-1). Among them, compound 6i was the most potent against HepG2 and MCF-7 cell lines, with IC50 values of 9.27 and 8.87 μM, respectively. The results suggest that the incorporation of a hydrazide-hydrazone side chain at the C-28 position of betulin is beneficial for compounds to display significant cytotoxicity. Compound 6i may be used as a promising skeleton for antitumor agents with improved efficacy.

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36

Tzankova, Diana, Lily Peikova, Stanislava Vladimirova, and Maya Georgieva. "Development and validation of RP-HPLC method for stability evaluation of model hydrazone, containing a pyrrole ring." Pharmacia 66, no. 3 (November 12, 2019): 127–34. http://dx.doi.org/10.3897/pharmacia.66.e47035.

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RP-HPLC method with UV detection was developed and validated for determination of the chemical stability and stability in close to physiological conditions of a model pyrrole hydrazone ethyl 5-(4-bromophenyl)-1-(1-(2-(4-hydroxy-3-methoxybenzylidene) hydrazineyl)-4-methyl-1-oxopentan-2-yl)-2-methyl-1H-pyrrole-3-carboxylate (D_5d), containing susceptible to hydrolysis hydrazone group. The evaluated substance was subjected to the influence of a variety of pH , representing the main physiological values of 37°C and corresponding pH values in the stomach (pH 2.0), blood (pH 7.4) and small intestine (pH 9.0). Chemical stability in a highly alkaline medium with a pH of 13.0 was also evaluated. The hydrazone I tested was found to be stable at pH 7.4 and pH 9.0 and 37 ° C and hydrolyzed under strong acidic (pH 2.0) and highly alkaline media (pH 13.0) and at the same temperature.The products of hydrolysis were identified to be the initial hydrazide and aldehyde, pointing the hydrazone group as most liable.

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37

Al-Humaidi, Jehan Y., Mohamed G. Badrey, Ashraf A. Aly, AbdElAziz A. Nayl, Mohie E. M. Zayed, Ohoud A. Jefri, and Sobhi M. Gomha. "Evaluation of the Binding Relationship of the RdRp Enzyme to Novel Thiazole/Acid Hydrazone Hybrids Obtainable through Green Synthetic Procedure." Polymers 14, no. 15 (August 3, 2022): 3160. http://dx.doi.org/10.3390/polym14153160.

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The viral RNA-dependent RNA polymerase (RdRp) complex is used by SARS-CoV-2 for genome replication and transcription, making RdRp an interesting target for developing the antiviral treatment. Hence the current work is concerned with the green synthesis, characterization and docking study with the RdRp enzyme of the series of novel and diverse hydrazones and pyrazoles. 4-Methyl-2-(2-(1-phenylethylidene)hydrazineyl)thiazole-5-carbohydrazide was prepared and then condensed with different carbonyl compounds (aldehydes and ketones either carbocyclic aromatic or heterocyclic) afforded the corresponding hydrazide-hydrazones. The combination of the acid hydrazide with bifunctional reagents such as acetylacetone, β-ketoesters (ethyl acetoacetate and ethyl benzoylacetate) resulted in the formation of pyrazole derivatives. The synthesized compounds were all obtained through grinding method using drops of AcOH. Various analytical and spectral analyses were used to determine the structures of the prepared compounds. Molecular Operating Environment (MOE®) version 2014.09 was used to estimate interactions between the prepared thiazole/hydrazone hybrids and RdRp obtained from the protein data bank (PDB: 7bv2) using enzyme-ligand docking for all synthesized derivatives and Remdesivir as a reference. Docking results with the RdRp enzyme revealed that the majority of the investigated drugs bind well to the enzyme via various types of interactions in comparison with the reference drug.

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38

Zhu, Xu, and Shunsuke Chiba. "TEMPO-mediated allylic C–H amination with hydrazones." Org. Biomol. Chem. 12, no. 26 (2014): 4567–70. http://dx.doi.org/10.1039/c4ob00839a.

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TEMPO-mediated reactions of alkenyl hydrazones afforded azaheterocycles via sp³ C–H allylic amination. The transformation is featured by a sequence of remote allylic H-radical shift and allylic homolytic substitution with hydrazone radicals.

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39

Siyal, Ali N., Saima Q. Memon, Sajida Parveen, Asma Soomro, Mazhar I. Khaskheli, and M. Y. Khuhawar. "Chemical Recycling of Expanded Polystyrene Waste: Synthesis of Novel Functional Polystyrene-Hydrazone Surface for Phenol Removal." Journal of Chemistry 2013 (2013): 1–8. http://dx.doi.org/10.1155/2013/842435.

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Expanded polystyrene (EPS) waste was chemically recycled to a novel functional polystyrene-hydrazone (PSH) surface by acetylation of polystyrene (PS) and then condensation with phenyl hydrazine. The synthesized surface was characterized by the FT-IR and elemental analysis. Synthesized novel functional PSH surface was successfully applied for the treatment of phenol-contaminated industrial wastewater by solid-phase extraction. Multivariant sorption optimization was achieved by factorial design approach. 99.93% of phenol was removed from aqueous solution. FT-IR study showed the involvement of nitrogen of hydrazone moiety of synthesized surface for the uptake of phenol through the hydrogen bonding.

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40

Khattab, Tawfik A., Ahmed A. Allam, Sarah I. Othman, May Bin-Jumah, Hanan M. Al-Harbi, and Moustafa M. G. Fouda. "Synthesis, Solvatochromic Performance, pH Sensing, Dyeing Ability, and Antimicrobial Activity of Novel Hydrazone Dyestuffs." Journal of Chemistry 2019 (February 5, 2019): 1–10. http://dx.doi.org/10.1155/2019/7814179.

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New tricyanofuran intramolecular charge transfer dyes comprising the hydrazone group were prepared and fully characterized in order to study their possible solvatochromism, dyeing ability, and antimicrobial activity. The preparation of the hydrazone dyes was achieved in relatively good yields starting from different aromatic amines. The hydrazone functional group was presented via the azo-coupling reaction of the tricyanofuran compound by the properly substituted diazonium chloride. Chemical structures of the prepared hydrazones were confirmed via nuclear magnetic resonance spectroscopy (1H- and 13C-NMR), Fourier-transform infrared spectroscopy (FT-IR), and elemental analysis (C, H, and N). The UV-visible absorption spectra of the produced sensor colorants displayed interesting solvatochromism in solvents with a different polarity, which was found to be affected by the substituents bonded to the aromatic hydrazone moiety. The pH molecular switching was investigated through tuning the intramolecular charge transfer stimulated by the reversible deprotonation/protonation process in acetonitrile solution showing color change from yellow to purple. The produced disperse dyestuffs were employed for dyeing polyester fibers to introduce acceptable color strength and colorfastness properties. Moreover, the dyes verified a weak to moderate antimicrobial activity against some selected pathogens, including S. aureus, E. coli, and Candida albicans.

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Shaji, Neethu, Sandhya M J Nair, and Shaiju S Dharan. "Coumarin Hydrazide: Chemistry, Synthesis and Pharmacological Activities - A Review." International Journal of Research and Review 9, no. 12 (December 8, 2022): 16–26. http://dx.doi.org/10.52403/ijrr.20221202.

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Coumarins are heterocyclic compound with a benzopyrone structure. Coumarins are a large group of organic compounds found in several plants even in bacteria and fungi. The biological activities of coumarins and its derivatives includes anticoagulant, anticancer, antiulcer, antifungal, anti-HIV, antimicrobial, antiosteoporosis, antioxidant and anti- inflammatory activity. Hydrazide-hydrazone derivatives act as structural sub units in many pharmacologically active compounds including coumarins to give biological activities like antimicrobial, anticancer, antifungal, anti-inflammatory, antiviral, anti-tubercular, and antiprotozoal activity. The interest in the synthesis of coumarin derivatives has been gaining importance over the last decades, reflecting the importance of such compounds in both medical and chemical research. In this review hydrazide-hydrazone derivatives of coumarins are taken into consideration and emphasised on the anticancer, antitubercular, antimicrobial, antioxidant and antidiabetic activity of these derivatives. Keywords: Coumarin, hydrazide, heterocyclic, benzopyran, antitumor, antimicrobial, antioxidant

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42

Choi, Heekyoung, Junho Ahn, Sungmin Kim, Hyungjun Kim, and Jong Hwa Jung. "Control of the mechanical strength of a bipyridine-based polymeric gel from linear nanofibre to helix with a chiral dopant." Chemical Communications 52, no. 48 (2016): 7600–7603. http://dx.doi.org/10.1039/c6cc03453e.

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A mixture of the building blocks 1 and 2 having hydrazine moieties and aldehyde moieties, respectively, formed a gel by a hydrazone reaction in the absence and presence of cyclohexane diamines as a chiral dopant and Fe²⁺.

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43

Sun, Zi-Qiang, Shun-Feng Yu, Xin-Lan Xu, Xiao-Yang Qiu, and Shu-Juan Liu. "Two Vanadium(V) Complexes Derived from Bromo and Chloro-Substituted Hydrazone Ligands: Syntheses, Crystal Structures and Antimicrobial Property." Acta Chimica Slovenica 67, no. 4 (December 15, 2020): 1281–89. http://dx.doi.org/10.17344/acsi.2020.6236.

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Two vanadium(V) complexes derived from the bromo and chloro-substituted hydrazones N’-(4-bromo-2-hydroxybenzylidene)- 2-chlorobenzohydrazide (H2L1) and N’-(3-bromo-5-chloro-2-hydroxybenzylidene)-3-methylbenzohydrazide (H2L2) with the formula [VOL1(OCH3)(CH3OH)] (1) and [VOL2(OCH3)(CH3OH)] (2) were newly synthesized and characterized by IR, UV-Vis and 1H NMR spectroscopy. The structures of H2L1 and the complexes were further confirmed by single crystal X-ray diffraction. Both vanadium complexes are mononuclear, with the metal atoms coordinated by the hydrazone ligands, methanol ligands, and methanolate ligands, and the oxo groups, forming octahedral geometry. The hydrazones and the vanadium complexes were assayed for the antimicrobial activities on Bacillus subtilis, Staphylococcus aureus, Escherichia coli, and Pseudomonas fluorescence, and the fungi Candida albicans and Aspergillus niger. The existence of the bromo and chloro groups in the hydrazone ligands may improve the antimicrobial property.

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44

Fernandez, María Alejandra, Juan Camilo Barona, Dorian Polo-Cerón, and Manuel N. Chaur. "Estudios fotoquímicos y electroquímicos de complejos lantánidos de 6-(hidroximetil)piridin- 2-carboxaldehído[2- metilpirimidina-4,6-diil] bishidrazona." Revista Colombiana de Química 43, no. 1 (October 5, 2015): 5–11. http://dx.doi.org/10.15446/rev.colomb.quim.v43n1.50540.

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<p>Herein we report the synthesis of the 6-(hydroxymethyl)pyridine-2- carboxaldehyde[2-methyl-pyrimidine- 4,6-diyl]bis-hydrazone by a condensation reaction between 6-(hydroxymethyl) picolinaldehyde with 4,6-(bis-hydrazino)-2- methylpyrimidine. This bis-hydrazone can be visualized as a two-arm system which exhibits photochemical induced [E,E]/[E,Z]/[Z,Z’] isomerizations and double coordination to metal centers. Configurational changes, upon UV light irradiation, were followed over time by 1 H NMR, establishing that isomerization, in both arms, is a consecutive reaction that follows first-order kinetics (k1 = 4.06 x 10-4 s-1 and k2 = 2.80 x 10-4 s-1). Furthermore, the synthesis of bis-hydrazone metal complexes with La (III) and Sm (III) ions was achieved; subsequently, the absorption and emission properties of these complexes were studied, determining the fluorescence quantum yields, 𝟇La= 0.2024 and 𝟇Sm= 0.1413. Electrochemical studies of the complexes were conducted by square wave voltammetry, demonstrating that the bis-hydrazone and its complexes are electroactive species between +1.5 and -2.5 V.</p>

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Nogueira, Thais Cristina Mendonça, Lucas dos Santos Cruz, Maria Cristina Lourenço, and Marcus Vinicius Nora de Souza. "Design, Synthesis and Anti-tuberculosis Activity of Hydrazones and N-acylhydrazones Containing Vitamin B6 and Different Heteroaromatic Nucleus." Letters in Drug Design & Discovery 16, no. 7 (June 27, 2019): 792–98. http://dx.doi.org/10.2174/1570180815666180627122055.

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Background: The term vitamin B6 refers to a set of six compounds, pyridoxine,pyridoxal ,and pyridoxamine and their phosphorylated forms, among which pyridoxal 5´-phosphate (PLP) is the most important and active form acting as a critical cofactor. These compounds are very useful in medicinal chemistry because of their structure and functionalities and are also used in bioinorganic chemistry as ligands for complexation with metals. Methods: In this study, a series of hydrazones 1a-g and N-acylhydrazones 2a-f containing vitamin B6 have been synthesized from commercial pyridoxal hydrochloride and the appropriate aromatic or heteroaromatic hydrazine or N-acylhydrazine. All synthesized compounds have been fully characterized and tested against Mycobacterium tuberculosis. Results: Among the N-acylhydrazones derivatives 2a-f, 2d (para- pyridine substituted Nacylhydrazone; MIC = 10.90 µM) exhibited the best activity. The ortho-pyridine derivative 2b exhibited intermediate activity (MIC = 87.32 µM), and the meta-pyridine derivative 2c was inactive. In case of the hydrazone series 1a-g, 7-chloroquinoxaline derivative 1f (MIC = 72.72 µM) showed the best result, indicating that the number of nitrogen and chlorine atoms in the radical moiety play an important role in the anti-tuberculosis activity of the quinoxaline derivatives (1f and 1g). Conclusion: The data reported herein indicates that the isoniazid derivative 2d (MIC = 10.90 µM) exhibited the best activity in the N-acylhydrazone series and; the quinoxaline nucleus derivative 1f (MIC = 72.72 µM) was the most active compound in the hydrazone series.

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46

Hebenbrock, Marian, and Jens Müller. "1H-[1,2,4]Triazolo[4,3-a]pyridin-4-ium and 3H-[1,2,4]triazolo[4,3-a]quinolin-10-ium derivatives as new intercalating agents for DNA." Zeitschrift für Naturforschung B 73, no. 11 (November 27, 2018): 885–93. http://dx.doi.org/10.1515/znb-2018-0089.

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AbstractTwo new cationic DNA intercalators, 3-phenyl-1-(6-phenylpyridin-2-yl)-1H-[1,2,4]triazolo[4,3-a]pyridin-4-ium (1a)+ and 1-phenyl-3-(6-phenylpyridin-2-yl)-3H-[1,2,4]triazolo[4,3-a]quinolin-10-ium (1b)+, were synthesized from 2-chloropyridine and 2-chloroquinoline, respectively, in a four-step procedure. Generation of the hydrazine, followed by condensation with an aldehyde to give a hydrazone and subsequent Buchwald-Hartwig amination gave a mixture of E- and Z-configured N,N-functionalized hydrazones. Finally, oxidative cyclisation gave rise to the formation of the cationic DNA intercalators, whose molecular structures were determined by single-crystal X-ray diffraction analysis of the hexafluorophosphate and tribromide salt of (1a)+ and (1b)+, respectively. The intercalative binding of (1a)PF6 and (1b)PF6 to ctDNA was confirmed by means of UV, CD and luminescence spectroscopy, determination of the DNA melting temperature and by rheology measurements.

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Liu, Yu Ting, Zhi Peng Yang, and Da Wei Yin. "Synthesis and Antibacterial Activity of Acetyl Ferrocene Hydrazine Hydrazone and its Metal Complexes." Advanced Materials Research 413 (December 2011): 459–62. http://dx.doi.org/10.4028/www.scientific.net/amr.413.459.

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Acetyl ferrocene hydrazine hydrazone and its novel metal complexes were synthesized. The structures were confirmed by elemental analysis, IR, molar conductance and thermo gravimetric analysis. The antibacterial activity was tests the result showed that the antibacterial activities of the complexes were significantly improved comparing with ligands.

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Wang, Lingyun, Xianggen Chen, and Derong Cao. "A cyanide-selective colorimetric “naked-eye” and fluorescent chemosensor based on a diketopyrrolopyrrole–hydrazone conjugate and its use for the design of a molecular-scale logic device." RSC Advances 6, no. 99 (2016): 96676–85. http://dx.doi.org/10.1039/c6ra21669b.

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A novel diketopyrrolopyrrole (DPP)–hydrazone based receptor was designed and synthesized as a selective fluorescent and colorimetric chemosensor for cyanide in aqueous media via deprotonation between the hydrazide moiety of the probe and cyanide.

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Atta-Allah, Saad R., Wael S. I. Abou-Elmagd, Kamal A. A. Kandeel, Magdy M. Hemdan, David S. A. Haneen, and Ahmed S. A. Youssef. "Synthesis and Antimicrobial Activity Evaluation of Some Novel Hydrazone, Pyrazolone, Chromenone, 2-Pyridone and 2-Pyrone Derivatives." Journal of Chemical Research 41, no. 11 (November 2017): 617–23. http://dx.doi.org/10.3184/174751917x15065183733150.

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A cyanoacetohydrazide derivative underwent a series of reactions with different nucleophilic reagents, such as hydrazine hydrate, p-chlorobenzaldehyde and salicylaldehyde, to give the condensation products. In addition, an arylidene malononitrile was reacted with different nitrogen nucleophiles, such as hydrazine hydrate, thiocarbohydrazide and cyanoacetohydrazide, to afford the hydrazine, hydrazone and pyridin-2-one derivatives, respectively. Furthermore, a pyridin-2-one derivative was reacted with different carbon electrophiles, such as carbon disulfide, p-chlorobenzaldehyde and acetic anhydride. The antimicrobial activities of some of the compounds were examined.

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Qiu, Xiao Yang, An Ran Shi, and Xiao Li Zhang. "Synthesis and Cytotoxic Activity of Salicyloyl Hydrazone Derivatives." Applied Mechanics and Materials 320 (May 2013): 522–25. http://dx.doi.org/10.4028/www.scientific.net/amm.320.522.

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Three salicyloyl hydrazone derivatives (compounds 1-3) were prepared by reacting salicyloyl hydrazine with substituted formaldehydes. Their structures were characterized by melting point, 1H-NMR, ESI-MS and elemental analyses. The cytotoxic activity of compounds 1-3 was evaluated in vitro against Hela cells (human cervical cancer cells). The results revealed that all the compounds showed cytotoxic activity, with IC50 values lower than 15 μM.

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Journal articles on the topic 'Hydrazone'

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