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Journal articles on the topic 'Pyridazinone Synthesis'

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Published: 4 June 2021

Last updated: 2 February 2022

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1

Deeb, Ali, Besher Bayoumy, Fathy Yasine, and Rida Fikry. "Pyridazine Derivatives and Related Compounds, Part 4. Pyrrolo[2,3-c]pyridazines and Furo[2,3-c]pyndazines, Synthesis and Some Reactions." Zeitschrift für Naturforschung B 47, no. 3 (March 1, 1992): 418–23. http://dx.doi.org/10.1515/znb-1992-0320.

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Ethyl 5-amino-3,4-diphenyl-7H-pyrrolo[2,3-c]pyridazine-6-carboxylate (1), ethyl 5-aminofuro[ 2,3-c]pyridazine-6-carboxylate (2) and 5-aminofuro[2,3-c]pyridazine-6-carboxamide (3), are obtained from 4-cyano-5,6-diphenyl-3(2H)-pyridazinone. 5-Acetamido and 5-chloroacetamido derivatives prepared from 1, undergo cyclization on heating to form 2-substituted pyridazino[4',3':4,5]pyrrolo[3,2-d]oxazin-4(5H)-one (5a, b). The reaction of 1 and 2 with hydrazine gave 6-carbohydrazide derivatives (7 a, b). Compound 3 undergoes condensation with acetyl chloride, chloroacetyl chloride, benzoyl chloride, formamide and carbon disulphide to furnish the corresponding pyrimido[4',5' :4,5]furo[2,3-c]pyridazin-4(3 H)-one derivatives. The reaction of 1 with o-aminophenol gave 3,4-diphenyl-11-oxo-10,11-dihydro-12H -pyridazino[ 4',3' :4,5]pyrrolo[3,2-b][1,5]benzoxazepine.

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2

Rimaz, Mehdi, Jabbar Khalafy, and Peyman Najafi Moghadam. "A Regioselective One-Pot, Three Component Synthesis of 6-Aryl-4-cyano-3(2H)-pyridazinones in Water." Australian Journal of Chemistry 63, no. 9 (2010): 1396. http://dx.doi.org/10.1071/ch09602.

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A series of 4-cyano-3(2H)-pyridazinones bearing different aryl substituents in the 6-position of the pyridazinone ring was synthesized regioselectively using a novel efficient one-pot three component reaction of alkyl 2-cyanoacetates with arylglyoxals in the presence of hydrazine hydrate at room temperature in water.

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3

Hovakimyan, S. A., A. V. Babakhanyan, V. S. Voskanyan, V. E. Karapetian, G. A. Panosyan, and S. T. Kocharian. "Synthesis of Pyridazinone Derivatives." Chemistry of Heterocyclic Compounds 40, no. 8 (August 2004): 1047–51. http://dx.doi.org/10.1023/b:cohc.0000046696.37815.62.

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4

Tao, Jing. "Synthesis of Aldehyde Hydrazones Containing Pyridazinone." Advanced Materials Research 361-363 (October 2011): 2008–11. http://dx.doi.org/10.4028/www.scientific.net/amr.361-363.2008.

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The reaction of 1,4,5,6-tetrahydro-6-pyridazinone-3-carboxylic acid hydrazides (1) and 1,6-dihydro-6-pyridazinone-3-carboxylic acid hydrazides (2) with four kind of substituted 3-formyl chromones (3a-3d) and five kind of 1-phenyl-3-aryl-4-formylpyrazoles (3e-3i) afforded the new compounds aldehyde hydrazones (4a-4i) and (5a-5i). Their structures were established by IR, 1H NMR and elemental analysis.

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5

Asif, Mohammad. "Some Conventional and Convenient Process for Functionalization of 6-Phenyl-4,5-Dihydropyridazinone Compounds." Asian Journal of Chemistry and Pharmaceutical Sciences 1, no. 1 (November 21, 2016): 41. http://dx.doi.org/10.18311/ajcps/2016/8375.

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The pyridazinone derivatives, particularly those bearing substituted different group or atom at a different position, have attracted considerable attention due to their characteristic pharmacological and other anticipated activities. These activities promoted the synthesis of a large number of substituted pyridazinone derivatives in order to explore the usefulness of this heterocyclic system. In the present review, various synthetic methods have been studied for the synthesis of substituted pyridazinone derivatives. The behaviour of the pyridazinone toward formaldehyde/piperidine, ethyl chloroacetate, chloroacetic acid, benzene sulfonyl chloride, bromine/acetic acid and aromatic aldehydes has also been studied. However, the reactions of the chloro derivative resulting from the reaction of pyridazinone with phosphorus oxychloride (POCl<sub>3</sub>). The behavior of chloropyridazine toward hydrazines, thiourea, sodium azide, anthranilic acid, aromatic amines and sulfa compounds have also been taken into consideration. Thethiopyridazinone derivativeswere prepared from the reaction of pyridazinone with phosphorus pentasulphide (P<sub>2</sub>S<sub>5</sub>). All the structures of were established on the based of spectroscopic data.<p> </p><p><strong> </strong></p>

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6

Wasfy, Ashraf A. F., Mohamed M. H. Arief, Mahassen S. Amine, Shafey G. Donia, and Aly A. Aly. "γ-Oxo Carboxylic Acids in Heterocyclic Synthesis, III. Synthesis of Biologically Active 4-Benzylamino-6-(5,5-dioxodibenzothiophen- 2-yl)-2,3,4,5-tetrahydropyridazin-3-ones." Zeitschrift für Naturforschung B 57, no. 6 (June 1, 2002): 668–76. http://dx.doi.org/10.1515/znb-2002-0613.

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α-Benzylamino-β-(5,5-dioxodibenzothiophen-2-carbonyl)propionic acid (1) has been synthesized by treating the corresponding β-aroylacrylic acid with benzylamine in dry benzene. On treatment with hydrazine hydrate the keto acid 1 furnishes the corresponding pyridazinone derivative 2. The behaviour of 2 towards carbon electrophiles, namely, ethyl chloroacetate, acrylonitrile, formaldehyde and secondary amines (under Mannich reaction conditions), aromatic aldehydes and carbon nucleophiles, namely, POCl3/PCl3 and P2S5 has been investigated. The 3-chloropyridazine derivative 13 reacts with hydrazine hydrate to give the 3-hydrazino derivative 14. On treatment with ethyl acetoacetate and/or acetylacetone the hydrazine 14 undergoes cyclization to afford pyrazolone derivative 16 and 3-(3,5-dimethylpyrazol- 1-yl)pyridazine derivative 17, respectively. On reaction with acetylhydrazine in boiling butanol and/or sodium azide in DMF the 3-chloropyridazine derivative 13 affords the triazolo[4,3-b]pyridazine 18 and the tetrazolo[1,5-b]pyridazine 19, respectively. The anti-microbial activity of the synthesized derivatives has been investigated.

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7

Samanta, Kartick Chandra, Mohd Asif, Pooja, Vikas Garg, Priyanka Sharma, and Ravinder Singh. "Synthesis of Different Substituted Pyridazinone Derivatives and Their Anticonvulsant Activity." E-Journal of Chemistry 8, no. 1 (2011): 245–51. http://dx.doi.org/10.1155/2011/873470.

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6-Phenyl(3᾽-imino-benzylidene)-2,3,4,5-tetrahydro pyridazin-3-one derivatives were synthesized from 6-(3᾽-aminophenyl)-2,3,4,5-tetrahydro pyridazin-3-one by reaction with different aldehydes. The respective pyridazinone was prepared by cyclization of appropriateβ-(aminophenyl) propionic acid with hydrazine hydrate. The pyridazinone derivatives were tested for anticonvulsant activity by MES (maximal electro shock) method and found that few of them have shown significant anticonvulsant activity.

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8

Ismail, Magda M. F., Dalia H. S. Soliman, Mona H. Abd Elmoniem, and Ghehad A. R. Abdel Jaleel. "Synthesis, Molecular Modeling of Novel Substituted Pyridazinones and their Vasorelaxant Activities." Medicinal Chemistry 17, no. 2 (December 30, 2020): 171–86. http://dx.doi.org/10.2174/1573406416666200327191100.

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Background: Hypertension, one of the most common cardiovascular diseases that can cause coronary disease, stroke, myocardial infarction, and sudden death, it is the major contributor to cardiac failure as well as renal insufficiency. Objectives: As there are many cardio-active pyridazinone-base derivatives in clinical use, therefore, we aimed to synthesize a new series of pyridazin-3-ones and evaluate their vasorelaxant activity. Methods: A new series of synthesized compounds were carried out first by the synthesis of 6- flouroarylpyridazinones by cyclization of 3-(4-flourobenzoyl) propionic acid with hydrazine hydrate or arylhydrazines to provide the corresponding pyridazinone derivatives 2a-d. Mannich reaction was performed using morpholine or piperidine formaldehyde to obtain compounds 3a,b. On the other hand, reaction of 2a with various chloroacetamide intermediates, in dimethylformamide and potassium carbonate as a catalyst, afforded the target compounds 5a-c. The aromatic acid hydrazide intermediates 6a-g were prepared in 50-90% yield, by reacting to the prepared esters with hydrazine hydrate under reflux in ethanol. The two compounds 8a,b were prepared via condensation of 7a,b with ethyl chloroacetate in dry acetone. Finally, the target 2,4,6-trisubstituted pyridazinones 9a-c derivatives were obtained by the reaction of 7a with the appropriate aromatic aldehyde or substituted acetophenones. The new compounds were then evaluated for their vasorelaxant properties using isolated thoracic rat aortic rings. In addition, a homology model was built and molecular modeling simulation of these compounds into the active sites of the newly created α1a-adrenoceptor model was performed in order to predict and rationalize their affinities toward this receptor. Results: Among these compounds; 5a was the most potent, it exhibited approximately two-times the activity of prazosin (IC50 = 0.250, 0.487 mmol, respectively) also, fourteen compounds were more potent than prazosin.

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9

TAKAYA, MASAHIRO. "Studies on Pyridazinone Derivatives. XI. Synthesis and Antifungal Activity of Amino Derivatives of Pyridazinone." YAKUGAKU ZASSHI 107, no. 10 (1987): 819–22. http://dx.doi.org/10.1248/yakushi1947.107.10_819.

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10

HUSAIN, ASIF, AFTAB AHMAD, ANIL BHANDARI, and VEERMA RAM. "SYNTHESIS AND ANTITUBERCULAR ACTIVITY OF PYRIDAZINONE DERIVATIVES." Journal of the Chilean Chemical Society 56, no. 3 (2011): 778–80. http://dx.doi.org/10.4067/s0717-97072011000300013.

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11

Allart-Simon, Ingrid, Aurélie Moniot, Nicolo Bisi, Miguel Ponce-Vargas, Sandra Audonnet, Marie Laronze-Cochard, Janos Sapi, Eric Hénon, Frédéric Velard, and Stéphane Gérard. "Pyridazinone derivatives as potential anti-inflammatory agents: synthesis and biological evaluation as PDE4 inhibitors." RSC Medicinal Chemistry 12, no. 4 (2021): 584–92. http://dx.doi.org/10.1039/d0md00423e.

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12

Corsano, Stefano, Giovannella Strappaghetti, Rossana Scapicchi, and Olimpia Scalise. "Synthesis and bronchospasmolytic properties of some pyridazinone derivatives." Bioorganic & Medicinal Chemistry Letters 3, no. 12 (December 1993): 2713–16. http://dx.doi.org/10.1016/s0960-894x(01)80748-4.

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13

Siddiqui, Anees A., Ravinesh Mishra, and Mohammad Shaharyar. "Synthesis, characterization and antihypertensive activity of pyridazinone derivatives." European Journal of Medicinal Chemistry 45, no. 6 (June 2010): 2283–90. http://dx.doi.org/10.1016/j.ejmech.2010.02.003.

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14

Cherkalin, M. S., A. V. Kolobov, E. I. Chernoburova, M. A. Shchetinina, and I. V. Zavarzin. "Synthesis of steroid compounds containing a pyridazinone moiety." Russian Chemical Bulletin 67, no. 11 (November 2018): 2144–47. http://dx.doi.org/10.1007/s11172-018-2343-9.

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15

TAKAYA, MASAHIRO. "Studies on Pyridazinone Derivatives. XII. Synthesis and Analgesic Activity of 2-Phenyl-3(2H)-pyridazinone Derivatives." YAKUGAKU ZASSHI 107, no. 11 (1987): 910–13. http://dx.doi.org/10.1248/yakushi1947.107.11_910.

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16

Deeb, Ali Abdel Hamid, Fatma Abdel Rahman El-Mariah, and Heba Kamal Abd El-Mawgoud. "Pyridazine and its related compounds: Part 38. Pyrimido[1,2-b]pyridazinone, synthesis and some reactions." European Journal of Chemistry 6, no. 2 (June 30, 2015): 204–10. http://dx.doi.org/10.5155/eurjchem.6.2.204-210.1252.

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17

Saeed, Makarem M., Nadia A. Khalil, Eman M. Ahmed, and Kholoud I. Eissa. "Synthesis and anti-inflammatory activity of novel pyridazine and pyridazinone derivatives as non-ulcerogenic agents." Archives of Pharmacal Research 35, no. 12 (December 2012): 2077–92. http://dx.doi.org/10.1007/s12272-012-1205-5.

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18

Youssef, A. SA, M. I. Marzouk, H. MF Madkour, A. MA El-Soll, and M. A. El-Hashash. "Synthesis of some heterocyclic systems of anticipated biological activities via 6-aryl-4-pyrazol-1-yl-pyridazin-3-one." Canadian Journal of Chemistry 83, no. 3 (March 1, 2005): 251–59. http://dx.doi.org/10.1139/v05-045.

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6-Aryl-4-pyrazol-1-yl-pyridazin-3-one (1) reacted with a PCl5POCl3 mixture to give the 3-chloropyridazine derivative 3. Reaction of 3 with 2-hydroxybenzoylhydrazide and semicarbazide hydrochloride afforded 4 and 5. Reaction of 1 with ethyl chloroacetate gave 8. Reaction of 8 with hydrazine hydrate yielded the hydrazide 9. The hydrazide 9 condensed with the acetylenic ketones and esters 10a10d and acetylacetone to give the adducts 11a, 11b, 12, 13, and 14. Reacting 1 with formaldehyde and piperidine, morpholine, or piperazine, 3-bromopropanoic acid, acetic anhydride, p-toluenesulphonyl chloride, succinyl chloride, oxalyl chloride, ethanolamine, or ethyl chloroacetate gave the adducts 1522. The structures of all newly synthesized compounds were evidenced from their spectral and microanalytical data. Key words: 6-aryl-4-pyrazol-1-yl-pyridazinone derivative, 6-aryl-3-chloropyridazine derivative, 3,6-diaryl-1,2,4-triazino[4,3-b]pyridazine derivative, 6-aryl-3-ethoxycarbonylmethoxypyridazine derivative, 6-aryl-3-(ω-benzoylacetophenone)hydrazinocarbonylmethoxypyridazine.

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19

Zhou, Yuefen, Lian-Sheng Li, Jingjing Zhao, Peter Dragovich, Nebojsa Stankovic, Thomas Bertolini, Douglas Murphy, et al. "Synthesis of New Pyridazinone Derivatives: 2,6-Disubstituted 5-Hydroxy-3(2H)-pyridazinone-4-carboxylic Acid Ethyl Esters." Synthesis 2007, no. 21 (November 2007): 3301–8. http://dx.doi.org/10.1055/s-2007-990823.

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20

Darwish, Elham S., Mahmoud A. Abdelrahman, and Abdellatif M. Salaheldin. "Enamines in Heterocyclic Synthesis: A Novel Simple and Efficient Route to Condensed Pyridazines." Zeitschrift für Naturforschung B 66, no. 6 (June 1, 2011): 597–602. http://dx.doi.org/10.1515/znb-2011-0607.

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An efficient and easy preparation of enamine derivatives, via active methyl and methylene compounds by in situ-generated 1-(diethoxymethyl)piperidine, produced from the mixture of triethyl orthoformate/piperidine/DMF, are described. Some new pyridazinone derivatives have been synthesized from the reaction of enamines with hydrazine hydrate and cyanoacid hydrazide.

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21

Husain, Asif, Sushma Drabu, Nitin Kumar, M. Mumtaz Alam, and Aftab Ahmad. "Synthesis and biological evaluation of some new pyridazinone derivatives." Journal of Enzyme Inhibition and Medicinal Chemistry 26, no. 5 (January 27, 2011): 742–48. http://dx.doi.org/10.3109/14756366.2010.548810.

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22

Mantu, Dorina, Costel Moldoveanu, Alina Nicolescu, Calin Deleanu, and Ionel I. Mangalagiu. "A facile synthesis of pyridazinone derivatives under ultrasonic irradiation." Ultrasonics Sonochemistry 16, no. 4 (April 2009): 452–54. http://dx.doi.org/10.1016/j.ultsonch.2008.11.012.

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23

Meyer, E., A. C. Joussef, H. Gallardo, and L. de B. P. de Souza. "Synthesis of New 4,5‐Dihydro‐3(2H)‐pyridazinone Derivatives." Synthetic Communications 34, no. 5 (December 31, 2004): 783–93. http://dx.doi.org/10.1081/scc-120028351.

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24

El Rayes, Samir Mohamed, Ibrahim A. I. Ali, and Walid Fathalla. "Convenient Synthesis of Some Novel Pyridazinone‐Bearing Triazole Moieties." Journal of Heterocyclic Chemistry 56, no. 1 (November 19, 2018): 51–59. http://dx.doi.org/10.1002/jhet.3369.

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25

Abouzid, Khaled, Maha Abdel Hakeem, Omnya Khalil, and Yosria Maklad. "Pyridazinone derivatives: Design, synthesis, and in vitro vasorelaxant activity." Bioorganic & Medicinal Chemistry 16, no. 1 (January 2008): 382–89. http://dx.doi.org/10.1016/j.bmc.2007.09.031.

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26

Allerton, Charlotte M. N., Mark D. Andrews, Julian Blagg, David Ellis, Edel Evrard, Martin P. Green, Kevin K. C. Liu, et al. "Design and synthesis of pyridazinone-based 5-HT2C agonists." Bioorganic & Medicinal Chemistry Letters 19, no. 19 (October 2009): 5791–95. http://dx.doi.org/10.1016/j.bmcl.2009.07.136.

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27

Thota, Sridhar, and Ranju Bansal. "Synthesis of new pyridazinone derivatives as platelet aggregation inhibitors." Medicinal Chemistry Research 19, no. 8 (July 24, 2009): 808–16. http://dx.doi.org/10.1007/s00044-009-9232-6.

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28

Alagöz, Mehmet Abdullah, Zeynep Özdemir, Mehtap Uysal, Simone Carradori, Marialucia Gallorini, Alessia Ricci, Susi Zara, and Bijo Mathew. "Synthesis, Cytotoxicity and Anti-Proliferative Activity against AGS Cells of New 3(2H)-Pyridazinone Derivatives Endowed with a Piperazinyl Linker." Pharmaceuticals 14, no. 3 (February 25, 2021): 183. http://dx.doi.org/10.3390/ph14030183.

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Novel twenty-three 3(2H)-pyridazinone derivatives were designed and synthesized based on the chemical requirements related to the anti-proliferative effects previously demonstrated within this scaffold. The introduction of a piperazinyl linker between the pyridazinone nucleus and the additional (un)substituted phenyl group led to some compounds endowed with a limited cytotoxicity against human gingival fibroblasts (HGFs) and good anti-proliferative effects against gastric adenocarcinoma cells (AGS) as evaluated by MTT and LDH assays, using doxorubicin as a positive control. Successive analyses revealed that the two most promising representative compounds (12 and 22) could exert their effects by inducing oxidative stress as demonstrated by the hydrogen peroxide release and the morphological changes (cell blebbing) revealed by light microscopy analysis after the haematoxylin-eosin staining. Moreover, to further assess the apoptotic process induced by compounds 12 and 22, Bax expression was measured by flow cytometry. These findings enlarged our knowledge of the structural requirements in this scaffold to display valuable biological effects against cancerous cell lines.

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29

Für, Csilla Sepsey, Gergő Riszter, János Gerencsér, Áron Szigetvári, Miklós Dékány, László Hazai, György Keglevich, and Hedvig Bölcskei. "Synthesis of Spiro[cycloalkane-pyridazinones] with High Fsp3 Character." Letters in Drug Design & Discovery 17, no. 6 (June 29, 2020): 731–44. http://dx.doi.org/10.2174/1570180816666190710130119.

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Background: owadays, in course of the drug design and discovery much attention is paid to the physicochemical parameters of a drug candidate, in addition to their biological activity. Disadvantageous physicochemical parameters can hinder the success of a drug candidate. Objective: Lovering et al. introduced the Fsp3 character as a measure of carbon bond saturation, which is related to the physicochemical paramethers of the drug. The pharmaceutical research focuses on the synthesis of compounds with high Fsp3 character. Methods: To improve the physicochemical properties (clogP, solubility, more advantageous ADME profile, etc.) of drug-candidate molecules one possibility is the replacement of all-carbon aromatic systems with bioisoster heteroaromatic moieties, e.g. with one or two nitrogen atom containing systems, such as pyridines and pyridazines, etc. The other option is to increase the Fsp3 character of the drug candidates. Both of these aspects were considered in the design the new spiro[cycloalkanepyridazinones], the synthesis of which is described in the present study. Results: Starting from 2-oxaspiro[4.5]decane-1,3-dione or 2-oxaspiro[4.4]nonane-1,3-dione, the corresponding ketocarboxylic acids were obtained by Friedel-Crafts reaction with anisole or veratrole. The ketocarboxylic acids were treated by hydrazine, methylhydrazine or phenylhydrazine to form the pyridazinone ring. N-Alkylation reaction of the pyridazinones resulted in the formation of further derivatives with high Fsp3 character. Conclusion: A small compound library was obtained incorporating compounds with high Fsp3 characters, which predicts advantageous physico-chemical parameters (LogP, ClogP and TPSA) for potential applications in medicinal chemistry.

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30

Zhang, Luye, Yang Zhang, Chongnan Bao, Peng Yang, Erdong Li, Yaqi Meng, Fei Cui, et al. "Synthesis and Antitumor Activity of Novel 1,3-Disubstituted Pyridazinone Derivatives." Chinese Journal of Organic Chemistry 40, no. 3 (2020): 794. http://dx.doi.org/10.6023/cjoc201908012.

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31

Kojima, Akihiko, and Yasushi Kohno. "A mild and efficient synthesis of a chiral pyridazinone derivative." Tetrahedron 69, no. 5 (February 2013): 1658–62. http://dx.doi.org/10.1016/j.tet.2012.11.072.

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32

Tóth, György, Sándor Molnár, Tivadar Tamás, and Ildikó Borbély. "An Efficient Synthesis of 4,5-Dihydro-3(2H)-pyridazinone Derivatives." Synthetic Communications 27, no. 20 (October 1, 1997): 3513–23. http://dx.doi.org/10.1080/00397919708007072.

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33

Gokçe, Mehtap, Deniz Dogruer, and Mustafa Fethi Sahin. "Synthesis and antinociceptive activity of 6-substituted-3-pyridazinone derivatives." Il Farmaco 56, no. 3 (April 2001): 233–37. http://dx.doi.org/10.1016/s0014-827x(01)01037-0.

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34

Khaidem, Somila, S. Sarveswari, Richa Gupta, and V. Vijayakumar. "ChemInform Abstract: Synthesis and Biological Evaluation of Some Pyridazinone Derivatives." ChemInform 43, no. 39 (August 30, 2012): no. http://dx.doi.org/10.1002/chin.201239254.

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35

Siddiqui, Anees A., Ravinesh Mishra, and Mohammad Shaharyar. "ChemInform Abstract: Synthesis, Characterization and Antihypertensive Activity of Pyridazinone Derivatives." ChemInform 41, no. 39 (September 2, 2010): no. http://dx.doi.org/10.1002/chin.201039156.

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36

Partap, Sangh, Md Jawaid Akhtar, Mohammed Shahar Yar, Mohd Zaheen Hassan, and Anees Ahmad Siddiqui. "Pyridazinone hybrids: Design, synthesis and evaluation as potential anticonvulsant agents." Bioorganic Chemistry 77 (April 2018): 74–83. http://dx.doi.org/10.1016/j.bioorg.2018.01.001.

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37

Mohamed, Nadia Ragab, Manal Mohamed Talaat El-Saidi, Yasser Mahmoud Ali, and Mohamed Hilmy Elnagdi. "Microwaves in organic synthesis: Facile synthesis of biologically active pyridazinone and iminopyridazine derivatives." Journal of Heterocyclic Chemistry 44, no. 6 (November 2007): 1333–37. http://dx.doi.org/10.1002/jhet.5570440615.

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38

Aly Nada, Afaf, Nadia Ragab Mohamed, Asma Mohamed Mahran, and Ayman Wahba Erian. "The Utility of Phosphonium Ylides in Heterocyclic Synthesis: Synthesis of Pyridazinone and Tetrahydrocinnolinone Derivatives." Journal of Chemical Research, no. 7 (1997): 236. http://dx.doi.org/10.1039/a700368d.

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39

El Malah, Tamer, Hany F. Nour, Oussama Dehbi, Farouk M. E. Abdel-Megeid, Abeer Essam El-Din Mahmoud, Mamdouh Moawad Ali, and Salwa M. Soliman. "Click Synthesis, Anticancer Activity and Molecular Docking Studies on Pyridazinone Scaffolds." Current Organic Chemistry 22, no. 23 (December 17, 2018): 2300–2307. http://dx.doi.org/10.2174/1385272822666181029111943.

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40

ZHANG, Jie-bing, Xiao-yun CHAI, Shi-chong YU, Zhuo-liang GU, and Guo-hua ZHOU. "Synthesis of pyridazinone derivatives and study of their antiplatelet aggregation activity." Academic Journal of Second Military Medical University 29, no. 7 (January 8, 2010): 821–24. http://dx.doi.org/10.3724/sp.j.1008.2009.00821.

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41

Gong, Yong, J. Kent Barbay, Alexey B. Dyatkin, Tamara A. Miskowski, Edward S. Kimball, Stephen M. Prouty, M. Carolyn Fisher, et al. "Synthesis and Biological Evaluation of Novel Pyridazinone-Based α4Integrin Receptor Antagonists." Journal of Medicinal Chemistry 49, no. 11 (June 2006): 3402–11. http://dx.doi.org/10.1021/jm060031q.

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42

Yoshida, Noriyuki, Masahiro Aono, Takeshi Tsubuki, Katsuya Awano, and Tomoshige Kobayashi. "Enantioselective synthesis of a chiral pyridazinone derivative by lipase-catalyzed hydrolysis." Tetrahedron: Asymmetry 14, no. 5 (March 2003): 529–35. http://dx.doi.org/10.1016/s0957-4166(03)00030-2.

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Partap, Sangh, Mohammad Shahar Yar, Md Zaheen Hassan, Md Jawaid Akhtar, and Anees A. Siddiqui. "Design, Synthesis, and Pharmacological Screening of Pyridazinone Hybrids as Anticonvulsant Agents." Archiv der Pharmazie 350, no. 10 (September 1, 2017): 1700135. http://dx.doi.org/10.1002/ardp.201700135.

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Zou, Xiajuan, and Guiyu Jin. "Synthesis of pyridazinone-substituted 1,3,4-thiadiazoles, -1,3,4-oxadiazoles and -1,2,4-triazoles." Journal of Heterocyclic Chemistry 38, no. 4 (July 2001): 993–96. http://dx.doi.org/10.1002/jhet.5570380431.

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Tao, Jing, Duo-Zhi Wang, and Ling-Hua Cao. "Synthesis of 5-(6-Pyridazinone-3-yl)-2-Glycosylamino-1,3,4-Oxadiazoles." Journal of the Chinese Chemical Society 54, no. 5 (October 2007): 1287–92. http://dx.doi.org/10.1002/jccs.200700181.

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Tao, Jing, Duo-Zhi Wang, and Ling-Hua Cao. "Synthesis of 5-(6-Pyridazinone-3-yl)-2-glycosylamino-1,3,4-thiadiazoles." Journal of the Chinese Chemical Society 57, no. 5A (October 2010): 1077–80. http://dx.doi.org/10.1002/jccs.201000151.

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SONMEZ, M., I. BERBER, and E. AKBAS. "Synthesis, antibacterial and antifungal activity of some new pyridazinone metal complexes." European Journal of Medicinal Chemistry 41, no. 1 (January 2006): 101–5. http://dx.doi.org/10.1016/j.ejmech.2005.10.003.

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Gong, Yong, J. Kent Barbay, Edward S. Kimball, Rosemary J. Santulli, M. Carolyn Fisher, Alexey B. Dyatkin, Tamara A. Miskowski, Pamela J. Hornby, and Wei He. "Synthesis and SAR of pyridazinone-substituted phenylalanine amide α4 integrin antagonists." Bioorganic & Medicinal Chemistry Letters 18, no. 4 (February 2008): 1331–35. http://dx.doi.org/10.1016/j.bmcl.2008.01.022.

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Sepsey Für, Csilla, and Hedvig Bölcskei. "New Spiro[cycloalkane-pyridazinone] Derivatives with Favorable Fsp3 Character." Chemistry 2, no. 4 (October 6, 2020): 837–48. http://dx.doi.org/10.3390/chemistry2040055.

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Abstract:

The large originator pharmaceutical companies need more and more new compounds for their molecule banks, because high throughput screening (HTS) is still a widely used method to find new hits in the course of the lead discovery. In the design and synthesis of a new compound library, important points are in focus nowadays: Lipinski’s rule of five (RO5); the high Fsp3 character; the use of bioisosteric heterocycles instead of aromatic rings. With said aim in mind, we have synthesized a small compound library of new spiro[cycloalkane-pyridazinones] with 36 members. The compounds with this new scaffold may be useful in various drug discovery projects.

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Szczukowski, Łukasz, Edward Krzyżak, Adrianna Zborowska, Patrycja Zając, Katarzyna Potyrak, Krzysztof Peregrym, Benita Wiatrak, Aleksandra Marciniak, and Piotr Świątek. "Design, Synthesis and Comprehensive Investigations of Pyrrolo[3,4-d]pyridazinone-Based 1,3,4-Oxadiazole as New Class of Selective COX-2 Inhibitors." International Journal of Molecular Sciences 21, no. 24 (December 17, 2020): 9623. http://dx.doi.org/10.3390/ijms21249623.

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Abstract:

The long-term use of Non-Steroidal Anti-Inflammatory Drugs (NSAIDs) in treatment of different chronic inflammatory disorders is strongly restricted by their serious gastrointestinal adverse effects. Therefore, there is still an urgent need to search for new, safe, and efficient anti-inflammatory agents. Previously, we have reported the Mannich base-type derivatives of pyrrolo[3,4-d]pyridazinone which strongly inhibit cyclooxygenase, have better affinity to COX-2 isoenzyme and exert promising anti-oxidant activity. These findings encouraged us to perform further optimization of that structure. Herein, we present the design, synthesis, molecular docking, spectroscopic, and biological studies of novel pyrrolo[3,4-d]pyridazinone derivatives bearing 4-aryl-1-(1-oxoethyl)piperazine pharmacophore 5a,b–6a,b. The new compounds were obtained via convenient, efficient, one-pot synthesis. According to in vitro evaluations, novel molecules exert no cytotoxicity and act as selective COX-2 inhibitors. These findings stay in good correlation with molecular modeling results, which additionally showed that investigated compounds take a position in the active site of COX-2 very similar to Meloxicam. Moreover, all derivatives reduce the increased level of reactive oxygen and nitrogen species and prevent DNA strand breaks caused by oxidative stress. Finally, performed spectroscopic and molecular docking studies demonstrated that new compound interactions with bovine serum albumin (BSA) are moderate, formation of complexes is in one-to-one ratio, and binding site II (subdomain IIIA) is favorable.

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