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Journal articles on the topic 'N-(1,3,4-oxadiazol-2-yl)benzamides'

Author: Grafiati

Published: 10 December 2022

Last updated: 29 January 2023

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1

Naclerio, George A., Nader S. Abutaleb, Marwa Alhashimi, Mohamed N. Seleem, and Herman O. Sintim. "N-(1,3,4-Oxadiazol-2-yl)Benzamides as Antibacterial Agents against Neisseria gonorrhoeae." International Journal of Molecular Sciences 22, no. 5 (2021): 2427. http://dx.doi.org/10.3390/ijms22052427.

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The Centers for Disease Control and Prevention (CDC) recognizes Neisseria gonorrhoeae as an urgent-threat Gram-negative bacterial pathogen. Additionally, resistance to frontline treatment (dual therapy with azithromycin and ceftriaxone) has led to the emergence of multidrug-resistant N. gonorrhoeae, which has caused a global health crisis. The drug pipeline for N. gonorrhoeae has been severely lacking as new antibacterial agents have not been approved by the FDA in the last twenty years. Thus, there is a need for new chemical entities active against drug-resistant N. gonorrhoeae. Trifluorometh

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2

Sravya, Gundala, Ummadi Nagarjuna, Venkatapuram Padmavathi, Galla Rajitha, Sakuri Chandi priya, and Adivireddy Padmaja. "Synthesis, Antioxidant and Anti-inflammatory Activities of 5-((styrylsulfonyl) methyl)-1,3,4-Oxadiazol / Thiadiazol-2-amine Derivatives." Letters in Drug Design & Discovery 16, no. 11 (2019): 1233–47. http://dx.doi.org/10.2174/1570180816666181102114529.

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Background: A new class of 5-(styrylsulfonylmethyl)-1,3,4-oxadiazol-2-amine and 5- (styrylsulfonylmethyl)-1,3,4-thiadiazol-2-amine derivatives were prepared by derivatization of amino function. Methods: All the synthesized compounds were tested for antioxidant and anti-inflammatory activities. Results: The 2-amino-3-chloro-N-(5-(4-methylstyrylsulfonylmethyl)-1,3,4-oxadiazol-2-yl)-propanamide (12b) and 3-chloro-N-(5-(4-methylstyrylsulfonylmethyl)-1,3,4-oxadiazol-2-yl)-butanamide (14b) displayed significant antioxidant activity, greater than the standard Ascorbic acid. Conclusion: Moreover, 12b

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3

Wu, Xiang-Wen, Wan-Fu Wu, Shi Yin, and Jian-Ping Ma. "Syntheses and structures of one CuI-containing coordination polymer and two macrocyclic supramolecular complexes based on flexible 1,3,4-oxadiazole-containing ligands." Acta Crystallographica Section C Structural Chemistry 71, no. 8 (2015): 683–89. http://dx.doi.org/10.1107/s2053229615012929.

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Three coordination complexes with CuIcentres have been prepared using the symmetrical flexible organic ligands 1,3-bis{[5-(quinolin-2-yl)-1,3,4-oxadiazol-2-yl]sulfanyl}propane (L1) and 1,4-bis{[5-(quinolin-2-yl)-1,3,4-oxadiazol-2-yl]sulfanyl}butane (L2). Crystallization ofL1 with Cu(SO3CF3)2and ofL2 with Cu(BF4)2and Cu(ClO4)2in a CH2Cl2/CH3OH mixed-solvent system at room temperature afforded the coordination complexescatena-poly[[copper(I)-μ-1,3-bis{[5-(quinolin-2-yl)-1,3,4-oxadiazol-2-yl]sulfanyl}propane] methanesulfonate dichloromethane 0.6-solvate], {[Cu(C25H18N6O2S2)](CF3SO3)·0.6CH2Cl2}n,

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4

Panchal, Ishan I., Roshani Rajput, and Ashish D. Patel. "Design, Synthesis and Pharmacological Evalution of 1,3,4-Oxadiazole Derivatives as Collapsin Response Mediator Protein 1 (CRMP 1) Inhibitors." Current Drug Discovery Technologies 17, no. 1 (2020): 57–67. http://dx.doi.org/10.2174/1570163815666181106090708.

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Objective: The series of 2-(4-Phenylamino)-N-(5-((4-nitrophenoxy)methyl) -1,3,4-oxadiazol- 2-yl)aceta-mide (5a-5e) and substituted N-(5-(Phenoxymethyl)-1,3,4-oxadiazol-2-yl)-2- (phenylamino)acetamide (5f-5i) was designed, synthesized and investigated for Collapsin Response Mediator Protein 1 (CRMP 1) inhibitors as small lung cancer. Design: Design of compounds was determined by literature review and molecular docking studies in iGEMDOCK 2.0. Materials and Methods: Novel 1, 3, 4 Oxadiazole derivatives were synthesized and characterized by melting point, TLC, IR Spectroscopy, Mass spectroscopy a

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5

Ahsan, Mohamed Jawed, Mohd Zaheen Hassan, Surender Singh Jadav, et al. "Synthesis and Biological Potentials of 5-aryl-N-[4-(trifluoromethyl) phenyl]-1,3,4-oxadiazol-2-amines." Letters in Organic Chemistry 17, no. 2 (2020): 133–40. http://dx.doi.org/10.2174/1570178616666190401193928.

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Oxadiazoles are an important class of heterocyclic compounds, having broad-spectrum activity. They were also reported as anticancer, and antioxidant agents, hence it is of significant importance to explore new oxadiazoles. A series of eleven (5-aryl-N-[4-(trifluoromethyl)phenyl]-1,3,4- oxadiazol-2-amines (6a-k) was synthesized based on the structures of reported compounds, SU-101, IMC38525, and FTAB. All these oxadiazoles were synthesized, characterized by spectral data, and further tested against melanoma, leukemia, colon, lung, CNS, ovarian, renal, breast and prostate cancer cell lines’ pane

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6

Ahsan, Mohamed Jawed, Lakshya Bhandari, Shally Makkar, et al. "Synthesis, Antiproliferative, and Antioxidant Activities of Substituted N-[(1,3,4-Oxadiazol-2-yl) Methyl] Benzamines." Letters in Drug Design & Discovery 17, no. 2 (2020): 145–54. http://dx.doi.org/10.2174/1570180816666181113110033.

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Background: Oxadiazole emerged as an important class of heterocyclic compound with diverse biological activities like anticancer, antitubercular, anticonvulsant, anti-tubulin, antimicrobial, anti-inflammatory, antioxidant etc. Objective: The objective of this study is to synthesis series of twelve substituted N-[(1,3,4-oxadiazol-2- yl)methyl]benzamines (6a-l) and their evaluation as antiproliferative and antioxidant agents. Methods: The substituted N-[(1,3,4-oxadiazol-2-yl)methyl]benzamines (6a-l) analogues were synthesized as per the reported procedure. The antiproliferative activity was test

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7

Wu, Xiang-Wen, Meng-Meng Xin, Jian-Ping Ma, Zhen-Hua Wu, and Yu-Bin Dong. "The coordination chemistry of two symmetric double-armed oxadiazole-bridged organic ligands with copper salts." Acta Crystallographica Section C Crystal Structure Communications 69, no. 6 (2013): 601–5. http://dx.doi.org/10.1107/s0108270113010913.

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Two new symmetric double-armed oxadiazole-bridged ligands, 4-methyl-{5-[5-methyl-2-(pyridin-3-ylcarbonyloxy)phenyl]-1,3,4-oxadiazol-2-yl}phenyl pyridine-3-carboxylate (L1) and 4-methyl-{5-[5-methyl-2-(pyridin-4-ylcarbonyloxy)phenyl]-1,3,4-oxadiazol-2-yl}phenyl pyridine-4-carboxylate (L2), were prepared by the reaction of 2,5-bis(2-hydroxy-5-methylphenyl)-1,3,4-oxadiazole with nicotinoyl chloride and isonicotinoyl chloride, respectively. LigandL1 can be used as an organic clip to bind CuIIcations and generate a molecular complex, bis(4-methyl-{5-[5-methyl-2-(pyridin-3-ylcarbonyloxy)phenyl]-1,3,

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8

Jin, Guoxia, Yuqi Ji, Teng Wang, et al. "Syntheses and characterization of dinuclear and tetranuclear AgI supramolecular complexes generated from symmetric and asymmetric molecular clips containing oxadiazole rings." Acta Crystallographica Section C Structural Chemistry 75, no. 10 (2019): 1327–35. http://dx.doi.org/10.1107/s2053229619011744.

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A new asymmetric ligand, 5-{3-[5-(4-methylphenyl)-1,3,4-oxadiazol-2-yl]phenyl}-2-(pyridin-3-yl)-1,3,4-oxadiazole (L5), which contains two oxadiazole rings, was synthesized and characterized. The assembly of symmetric 2,5-bis(pyridin-3-yl)-1,3,4-oxadiazole (L1) and asymmetric L5 with AgCO2CF3 in solution yielded two novel AgI complexes, namely catena-poly[[di-μ-trifluoroacetato-disilver(I)]-bis[μ-2,5-bis(pyridin-3-yl)-1,3,4-oxadiazole]], [Ag2(C2F3O2)2(C12H8N4O)2] n or [Ag2(μ2-O2CCF3)2(L1)2] n (1), and bis(μ3-5-{3-[5-(4-methylphenyl)-1,3,4-oxadiazol-2-yl]phenyl}-2-(pyridin-3-yl)-1,3,4-oxadiazole

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9

Nayak, Prakash, Badiadka Narayana, Seranthimata Samshuddin, and Balladka Sarojini. "2-{[5-(Diphenylmethyl)-1,3,4-oxadiazol-2-yl]sulfanyl}-N-(pyrazin-2-yl)acetamide." Molbank 2013, no. 2 (2013): M800. http://dx.doi.org/10.3390/m800.

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10

Marri, Srinivas, Ramu Kakkerla, Mudumba Phali Surya Murali Krishna, and Manchikatla Venkat Rajam. "Synthesis and antimicrobial evaluation of isoxazole-substituted 1,3,4-oxadiazoles." Heterocyclic Communications 24, no. 5 (2018): 285–92. http://dx.doi.org/10.1515/hc-2018-0137.

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Abstract Synthesis of N-(5-methylisoxazol-3-yl)-2-(5-aryl-1,3,4-oxadiazol-2-yl)acetamides 5a–k was achieved from readily available materials. The compounds were screened for their in vitro antimicrobial activity against representative bacterial and fungal strains. Compounds 5b, 5d and 5f exhibit good activity.

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11

Soares, Júlio C. A. V., and Luiza R. S. Dias. "N′-Acetyl-3-methyl-1,6-diphenyl-1H-pyrazolo[3,4-b]pyridine-4-carbohydrazide." Molbank 2020, no. 1 (2020): M1104. http://dx.doi.org/10.3390/m1104.

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Synthesis of N′-acetyl-3-methyl-1,6-diphenyl-1H-pyrazolo[3,4-b]pyridine-4-carbohydrazide from the phenyl acetates of 3-acetyl-5-(3-methyl-1,6-diphenyl-1H-pyrazolo[3,4-b]pyridine-4-yl)-2,3-dihydro-1,3,4-oxadiazol-2-yl in alkaline medium and its characterization by spectroscopic methods.

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12

Kaya, Betül, Weiam Hussin, Leyla Yurttaş, et al. "Design and Synthesis of New 1,3,4-Oxadiazole – Benzothiazole and Hydrazone Derivatives as Promising Chemotherapeutic Agents." Drug Research 67, no. 05 (2017): 275–82. http://dx.doi.org/10.1055/s-0042-119070.

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AbstractLooking for new cytotoxic and antimicrobial agents with improved antitumor activity, a series of hydrazide and oxadiazole derivatives were designed and synthesized using 3-methoxyphenol as starting substance. Novel N’-(arylidene)-2-(3-methoxyphenoxy)acetohydrazide derivatives (4a–f)/1-(4-substitutedphenyl)-2-[(5-[(3-methoxyphenoxy)methyl]-1,3,4-oxadiazol-2-yl)thio]ethan-1-one derivatives (6a–f)/N-(6-substitutedbenzothiazol-2-yl)-2-[(5-[(3-methoxyphenoxy)methyl]-1,3,4-oxadiazol-2-yl)thio]acetamide derivatives (7a–e) were obtained and evaluated for their in vitro antimicrobial activity a

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13

Paraschivescu, Codruţa C., Mihaela Matache, Cristian Dobrotă, et al. "Unexpected Formation of N-(1-(2-Aryl-hydrazono)isoindolin-2-yl)benzamides and Their Conversion into 1,2-(Bis-1,3,4-oxadiazol-2-yl)benzenes." Journal of Organic Chemistry 78, no. 6 (2013): 2670–79. http://dx.doi.org/10.1021/jo400023z.

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14

Shajari, Nahid, Reza Kazemizadeh, and Ali Ramazani. "Efficient one-pot, four-component synthesis of N,N-dibenzyl-N-{1-[5-(3-aryl)-1,3,4-oxadiazol-2-yl]cyclobutyl}amine derivatives from the reaction of (isocyanoimino)triphenylphosphorane, dibenzylamine, an aromatic carboxylic acid and cyclobutanone." Journal of the Serbian Chemical Society 77, no. 9 (2012): 1175–80. http://dx.doi.org/10.2298/jsc111014024s.

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Four-component reaction of cyclobutanone, dibenzylamine and (Nisocyanimino) triphenylphosphorane in the presence of aromatic carboxylic acids proceed smoothly at room temperature and under neutral conditions to afford N,N-dibenzyl-N-{1-[5-(3-aryl)-1,3,4-oxadiazol-2-yl]cyclobutyl}amine derivatives in high yields.

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15

Sharma, Divyanshu, Nitin Kumar, and Devender Pathak. "Synthesis, characterization and biological evaluation of some newer carbazole derivatives." Journal of the Serbian Chemical Society 79, no. 2 (2014): 125–32. http://dx.doi.org/10.2298/jsc130123069s.

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A series of novel 5-((9H-carbazol-9-yl)methyl)-N-((substituted phenyl)(piperazin-1-yl)methyl)-1,3,4-oxadiazol-2-amine (4a-4o) derivatives was synthesized by starting with carbazole which on reaction with ethyl choloroacetate yielded ethyl 2-(9H-carbazole-9-yl)acetate (1), compound (1) on reaction with semicarbazide followed by cyclisation with sulphuric acid gave 5-((9H-carbazole-9-yl)-1,3,4-oxadiazol-2-amine (3) which through Mannich reaction with piperazine and a variety of aromatic aldehydes in the presence of acetic acid yielded the titled compounds (4a-4o). The structures of compounds wer

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16

Zhong, Li, Zhu Zhixiang, Song Gonghua, Qian Xuhong, and Sun Jie. "The Crystal Structure of N-(5-Phenyl-1,3,4-oxadiazol-2-yl)-N′ -benzoyl Urea, a Novel Insect-growth Regulator." Journal of Chemical Research 23, no. 1 (1999): 66–67. http://dx.doi.org/10.1177/174751989902300139.

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The crystal structure of N-(5-phenyl-1,3,4-oxadiazol-2-yl)- N′-benzoyl urea, C16H12N4O3, a novel insect-growth-regulator (IGR), has been established; the crystal structure belongs to the triclinic system with Z = 2, and the urea linkage is coplanar with intramolecular hydrogen bond formation, making the structure analogous to a four-ring compound.

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17

Pokotylo, Ihor O., Pavlo V. Zadorozhnii, Vadym V. Kiselev, Oxana V. Okhtina, and Aleksandr V. Kharchenko. "Some New Heterocyclisations Based on N-(2,2-dichloro-1-isothiocyanatoethyl)benzamide Derivatives." Acta Chemica Iasi 27, no. 1 (2019): 65–72. http://dx.doi.org/10.2478/achi-2019-0005.

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Abstract Based on the readily available N-(2,2-dichloro-1-(2-(4-methylbenzoyl)-hydrazine-1-carbothioamido)ethyl)benzamide, the corresponding N-(2,2-dichloro-1-((5-(p-tolyl)-1,3,4-oxadiazol-2-yl)amino)ethyl)benzamide and 5-(p-tolyl)-1,3,4-thiadiazol-2-amine were obtained. The products were received in acceptable yields and were isolated from the reaction mixture without any particular difficulty. The structure of the compounds obtained was confirmed by 1H, 13C NMR spectroscopy and mass spectrometry data.

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18

Purushotham, Nikil, and Boja Poojary. "N-[2-(1H-Indol-3-yl)-1-(5-thioxo-4,5-dihydro-1,3,4-oxadiazol-2-yl)ethyl]-4-methylbenzenesulfonamide." Molbank 2018, no. 3 (2018): M1008. http://dx.doi.org/10.3390/m1008.

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N-[1-Hydrazinyl-3-(1H-indol-3-yl)-1-oxopropan-2-yl]-4-methylbenzenesulfonamide (1) on cyclization with carbon disulfide in ethanolic potassium hydroxide affords N-[2-(1H-indol-3-yl)-1-(5-thioxo-4,5-dihydro-1,3,4-oxadiazol-2-yl)ethyl]-4-methylbenzenesulfonamide (2) in 84% yield. The structure of compound 2 was supported by mass spectrometry, FT-IR and 1H- and 13C-NMR spectroscopy. To investigate the potential of compound 2 to act as antitubercular agent, it was docked against the enoyl reductase (InhA) enzyme of Mycobacterium tuberculosis. The docking pose and non-covalent interactions gave ins

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19

J Khairnar, Bhikan, Rahul S. Salunke, Premchand B. Patil, et al. "Synthesis and Antimicrobial Activity of Some New 1, 4-Benzothiazine Containing Thiosemicarbazides and 1, 3, 4-Oxadiazole Derivatives." E-Journal of Chemistry 9, no. 1 (2012): 318–22. http://dx.doi.org/10.1155/2012/902784.

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A series of novel 3- methyl-7-substituted-4H,4-benzothiazine-2-carbohydrazide (3a-e) and corresponding thiosemicarbazides (4-a-q); 2-[3-methyl-7-substituted- 4H-1, 4-benzothiazine-2-yl]-N-(aryl) hydrazine carbothiamide have been synthesized. The thiosemicarbazide when cyclized with iodine via intramolecular cyclisation gave benzothiazonyl oxadiazoles (5-a-q); 5-(3-methyl -7-substitued-4H- 1,4-benzothiazin-2-yl)-N—aryl- 1,3,4- oxadiazol -2-amine and the compounds were tested for antibacterial and antifungal activities against different microorganisms.

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20

Paraschivescu, Codruta C., Mihaela Matache, Cristian Dobrota, et al. "ChemInform Abstract: Unexpected Formation of N-(1-(2-Aryl-hydrazono)isoindolin-2-yl)benzamides and Their Conversion into 1,2-(Bis-1,3,4-oxadiazol-2-yl)benzenes." ChemInform 44, no. 30 (2013): no. http://dx.doi.org/10.1002/chin.201330148.

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21

Zareef, Muhammad, Rashid Iqbal, Javid H. Zaidi, Muhammad Arfan, and Masood Parvez. "N-{[1-(5-Benzylsulfanyl)-1,3,4-oxadiazol-2-yl]ethyl}-4-chlorobenzenesulfonamide." Acta Crystallographica Section E Structure Reports Online 62, no. 6 (2006): o2449—o2451. http://dx.doi.org/10.1107/s1600536806017557.

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22

Bordei Telehoiu, Alexandra T., Diana C. Nuță, Miron T. Căproiu, et al. "Design, Synthesis and In Vitro Characterization of Novel Antimicrobial Agents Based on 6-Chloro-9H-carbazol Derivatives and 1,3,4-Oxadiazole Scaffolds." Molecules 25, no. 2 (2020): 266. http://dx.doi.org/10.3390/molecules25020266.

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In this paper, we aimed to exploit and combine in the same molecule the carbazole and the 1,3,4-oxadiazole pharmacophores, to obtain novel carprofen derivatives, by using two synthesis pathways. For the first route, the following steps have been followed: (i) (RS)-2-(6-chloro-9H-carbazol-2-yl)propanonic acid (carprofen) treatment with methanol, yielding methyl (RS)-2-(6-chloro-9H-carbazol-2-yl)propanoate; (ii) the resulted methylic ester was converted to (RS)-2-(6-chloro-9H-carbazol-2-yl)propane hydrazide (carprofen hydrazide) by treatment with hydrazine hydrate; (iii) reaction of the hydrazid

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23

Souldozi, Ali, Katarzyna Ślepokura, Tadeusz Lis, and Ali Ramazani. "Synthesis And Single Crystal X-Ray Structure Of 2-(1,3,4-Oxadiazol- 2-yl)Aniline." Zeitschrift für Naturforschung B 62, no. 6 (2007): 835–40. http://dx.doi.org/10.1515/znb-2007-0613.

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Reaction of 2-aminobenzoic acid with (N-isocyanimino)triphenylphosphorane proceeds smoothly at r. t. to afford 2-(1,3,4-oxadiazol-2-yl)aniline in high yield. The structure of this compound was confirmed by IR, 1H, and 13C NMR spectroscopy, mass spectrometry, and single crystal X-ray structure determination. The X-ray structural analysis of the product indicated that its aromatic rings are approximately co-planar

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24

Sever, Belgin, Mehlika Dilek Altıntop, Ahmet Özdemir, et al. "In Vitro and In Silico Evaluation of Anticancer Activity of New Indole-Based 1,3,4-Oxadiazoles as EGFR and COX-2 Inhibitors." Molecules 25, no. 21 (2020): 5190. http://dx.doi.org/10.3390/molecules25215190.

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Epidermal growth factor receptor (EGFR) and cyclooxygenase-2 (COX-2) are crucial targetable enzymes in cancer management. Therefore, herein, new 2-[(5-((1H-indol-3-yl)methyl)-1,3,4-oxadiazol-2-yl)thio]-N-(thiazol/benzothiazol-2-yl)acetamides (2a–i) were designed and synthesized as EGFR and COX-2 inhibitors. The cytotoxic effects of compounds 2a–i on HCT116 human colorectal carcinoma, A549 human lung adenocarcinoma, and A375 human melanoma cell lines were determined using MTT assay. 2-[(5-((1H-Indol-3-yl)methyl)-1,3,4-oxadiazol-2-yl)thio]-N-(6-ethoxybenzothiazol-2-yl)acetamide (2e) exhibited th

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25

KHAN, R. H., and R. C. RASTOGI. "ChemInform Abstract: Synthesis of 3-(5-Aryl-1,3,4-oxadiazol-2-yl)quinazoline-2,4-(1H)- diones and 2-((5-Aryl-1,3,4-oxadiazol-2-yl)amino)-3,1-benzoxazin-4- ones from Methyl N-(5-Aryl-1,3,4-oxadiazol-2-yl)dithiocarbamates." ChemInform 24, no. 7 (2010): no. http://dx.doi.org/10.1002/chin.199307199.

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26

Han, Li-Ping, Bin Li, and Jie Liu. "N-Phenyl-N-{4-[5-(4-pyridyl)-1,3,4-oxadiazol-2-yl]phenyl}aniline." Acta Crystallographica Section E Structure Reports Online 64, no. 1 (2007): o242. http://dx.doi.org/10.1107/s1600536807065245.

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27

Paswan, Santosh, Manoj K. Bharty, Sanyucta Kumari, Sushil K. Gupta, and Nand K. Singh. "Crystal structure of 5-(furan-2-yl)-N-phenyl-1,3,4-oxadiazol-2-amine." Acta Crystallographica Section E Crystallographic Communications 71, no. 11 (2015): o880—o881. http://dx.doi.org/10.1107/s2056989015019453.

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The title compound, C12H9N3O2, was obtained as a cyclized oxadiazole derivative from substituted thiosemicarbazide in the presence of manganese(II) acetate. The furan ring is disordered over two orientations, with occupancies of 0.76 (2) and 0.24 (2). The dihedral angles between the central oxadiazole ring and the pendant phenyl ring and furan ring (major disorder component) are 3.34 (18) and 5.7 (6)°, respectively. A short intramolecular C—H...O contact generates anS(6) ring. In the crystal, inversion dimers linked by pairs of N—H...N hydrogen bonds generateR22[8] loops. The dimers are linked

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28

Syed, Tayyaba, Shahid Hameed, and Peter G. Jones. "(S)-N-[1-(5-Benzylsulfanyl-1,3,4-oxadiazol-2-yl)-2-phenylethyl]-4-methylbenzenesulfonamide." Acta Crystallographica Section E Structure Reports Online 67, no. 11 (2011): o2875—o2876. http://dx.doi.org/10.1107/s1600536811040669.

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29

Djebli, Yacine, Salima Mosbah, Sihem Boufas, Leila Bencharif, and Thierry Roisnel. "Bis{N-[5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl]ethanimidamidato}copper(II)." Acta Crystallographica Section E Structure Reports Online 66, no. 4 (2010): m410. http://dx.doi.org/10.1107/s1600536810009050.

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30

Han, Li-Ping, Bin Li, Jie Liu, and Qing-Chun Liu. "N-Phenyl-N-{4-[5-(2-phenyl-3-pyridyl)-1,3,4-oxadiazol-2-yl]phenyl}aniline." Acta Crystallographica Section E Structure Reports Online 63, no. 12 (2007): o4780. http://dx.doi.org/10.1107/s1600536807058382.

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31

Beliaev, Alexandre, Humberto S. Ferreira, David A. Learmonth, et al. "Synthesis and structure–activity relationships of ionizable 1,3,4-oxadiazol-2(3H)-ones as peripherally selective FAAH inhibitors with improved aqueous solubility." Pure and Applied Chemistry 88, no. 4 (2016): 341–47. http://dx.doi.org/10.1515/pac-2016-0104.

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AbstractNovel 5-(2,4-difluorophenoxy)-3-aryl-1,3,4-oxadiazol-2(3H)-ones were prepared and in vivo SAR are discussed. Ionisable substituents on the N-phenyl ring provided compounds with significantly improved aqueous solubility. In addition, these analogues retained equivalent or improved potency against FAAH enzyme compared to the parent phenols 2–3. FAAH inhibition by the 2-(piperazin-1-yl)ethyl and 3-(piperazin-1-yl)propyl derivatives 24 and 30 was confined to the periphery in mice (30 mg/kg), whereas hepatic FAAH activity was inhibited by over 90%.

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32

Wołek, Barbara, Mateusz Werłos, Magdalena Komander, and Agnieszka Kudelko. "Efficient Synthesis of Novel 1,3,4-Oxadiazoles Bearing a 4-N,N-Dimethylaminoquinazoline Scaffold via Palladium-Catalyzed Suzuki Cross-Coupling Reactions." Molecules 25, no. 21 (2020): 5150. http://dx.doi.org/10.3390/molecules25215150.

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Two series of novel (symmetrical and unsymmetrical) quinazolinylphenyl-1,3,4-oxadiazole derivatives were synthesized using palladium-catalyzed Suzuki cross-coupling reactions. The presented synthetic methodology is based on the use of bromine-substituted 2-phenyl-4-N,N-dimethylaminoquinazolines and either a boronic acid pinacol ester or a diboronic acid bis(pinacol) ester of 2,5-diphenyl-1,3,4-oxadiazole. The reactions are conducted in a two-phase solvent system in the presence of catalytic amounts of [1,1′-bis(diphenylphosphino)ferrocene]-dichloropalladium(II), sodium carbonate, and tetrabuty

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33

Ravinaik, B., M. V. B. Rao, P. T. S. R. K. P. Rao, D. Ramachandran, and D. R. S. Reddy. "Design, Synthesis, and Anticancer Evaluation of N-(4-{5-[4-(5-Methyl-1,3,4-oxadiazol-2-yl)phenyl]-4-(2,3,4-trimethoxyphenyl)-1,3-thiazol-2-yl}phenyl)benzamides." Russian Journal of Organic Chemistry 57, no. 4 (2021): 624–30. http://dx.doi.org/10.1134/s1070428021040187.

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34

Gao, Ru-Qin, Chao-Hui Xia та Guo-Ting Li. "catena-Poly[[diaquanickel(II)]-bis(μ-2-{[5-(pyridin-4-yl)-1,3,4-oxadiazol-2-yl]sulfanyl}acetato)]". Acta Crystallographica Section E Structure Reports Online 68, № 6 (2012): m763—m764. http://dx.doi.org/10.1107/s1600536812020259.

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In the title compound, [Ni(C9H6N3O3S)2(H2O)2] n , the NiII atom, located on an inversion center, is ligated in an octahedral geometry by two carboxylate O atoms from two 2-{[5-(pyridin-4-yl)-1,3,4-oxadiazol-2-yl]sulfanyl}acetate (L) ligands and two O atoms from water molecules in the equatorial plane, and two pyridine N atoms from other two L ligands at the apical sites. Two L ligands bridge pairs of metal atoms in an antiparallel manner, forming centrosymmetric dinuclear quasi-rectangular units which are linked into infinite double-stranded chains parallel to [100]. O—H...O hydrogen bonds bet

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35

Gudasi, Kalagouda, Manjula Patil, Ramesh Vadavi, Rashmi Shenoy, and Siddappa Patil. "Transition metal complexes with a new tridentate ligand, 5-[6-(5-mercapto- 1,3,4-oxadiazol-2-yl)pyridin-2-yl]-1,3,4-oxadiazole-2-thiol." Journal of the Serbian Chemical Society 72, no. 4 (2007): 357–66. http://dx.doi.org/10.2298/jsc0704357g.

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A new ligand 5-[6-(5-mercapto-1,3,4-oxadiazol-2-yl)pyridin-2-yl]-1,3,4-oxadiazole- 2-thiol (L) and its Mn(II), Co(II), Ni(II), Cu(II), and Zn(II) complexes were synthesized. The authenticity of the ligand and its transition metal complexes were established by elemental analyses, conductance and magnetic susceptibility measurements, as well as spectroscopic (IR, 1H- and 13C-NMR, electronic, mass, ESR) and thermal studies. The IR and 1H-NMR spectral studies revealed the existence of the ligand in the thiol form in the solid state, whereas in the thione form in the dissolved state. The magnetic a

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36

Muralikrishna, A., M. Kannan, V. Padmavathi, A. Padmaja, and R. Krishna. "N-(4-Chlorophenyl)-1-(5-{[(2-phenylethenyl)sulfonyl]methyl}-1,3,4-oxadiazol-2-yl)methanesulfonamide." Acta Crystallographica Section E Structure Reports Online 68, no. 10 (2012): o2954. http://dx.doi.org/10.1107/s1600536812037300.

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37

Desai, Nisheeth C., and Darshita V. Vaja. "Hybrid Approach for Synthesis and Antimicrobial Activity of Heterocyclic Compounds." International Letters of Chemistry, Physics and Astronomy 77 (January 2018): 35–52. http://dx.doi.org/10.18052/www.scipress.com/ilcpa.77.35.

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We have synthesized novel series of N-(1-(2-(1-phenyl-3-(p-tolyl)-1H-pyrazol-4-yl)-5-(pyridin-4-yl)-1,3,4-oxadiazol-3(2H)-yl)ethylidene)arylaniline and their derivatives. The structures of synthesized compounds were well characterized by spectroscopic techniques. Antimicrobial activity of the newly synthesized derivatives was evaluated against gram positive (S. aureus and S. pyogenes), gram negative bacteria (E. coli and P. aeruginosa), and strains of fungi (C. albicans, A. niger and A. clavatus). Among the screened derivatives 5c, 5f, 5i, 5l and 5t demonstrated superior antimicrobial activity

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38

Desai, Nisheeth C., and Darshita V. Vaja. "Hybrid Approach for Synthesis and Antimicrobial Activity of Heterocyclic Compounds." International Letters of Chemistry, Physics and Astronomy 77 (January 25, 2018): 35–52. http://dx.doi.org/10.56431/p-2746bu.

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We have synthesized novel series of N-(1-(2-(1-phenyl-3-(p-tolyl)-1H-pyrazol-4-yl)-5-(pyridin-4-yl)-1,3,4-oxadiazol-3(2H)-yl)ethylidene)arylaniline and their derivatives. The structures of synthesized compounds were well characterized by spectroscopic techniques. Antimicrobial activity of the newly synthesized derivatives was evaluated against gram positive (S. aureus and S. pyogenes), gram negative bacteria (E. coli and P. aeruginosa), and strains of fungi (C. albicans, A. niger and A. clavatus). Among the screened derivatives 5c, 5f, 5i, 5l and 5t demonstrated superior antimicrobial activity

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39

Lakshmithendral, K., K. Archana, K. Saravanan, S. Kabilan, and S. Selvanayagam. "Crystal structures of 3-methoxy-4-{[5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl]methoxy}benzonitrile and N-(4-{[5-(4-chlorophenyl)-1,3,4-oxadiazol-2-yl]methoxy}phenyl)acetamide." Acta Crystallographica Section E Crystallographic Communications 74, no. 12 (2018): 1919–22. http://dx.doi.org/10.1107/s2056989018016754.

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The title compounds, C18H15N3O4 and C17H14ClN3O3, are heterocyclic 1,3,4-oxadiazole derivatives which differ from each other in the groups attached to the carbon atoms: a methoxyphenyl ring and a benzonitrile group in (I) and a chlorophenyl ring and an acetamide group in (II). Short intramolecular C—H...O hydrogen bonds occur in both molecules. The crystal structure of (I) features C—H...N hydrogen bonds, while in the crystal structure of (II), N—H...N, C—H...N and C—H...O hydrogen bonds are observed.

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40

Naclerio, George A., Nader S. Abutaleb, Kenneth I. Onyedibe, Mohamed N. Seleem, and Herman O. Sintim. "Potent trifluoromethoxy, trifluoromethylsulfonyl, trifluoromethylthio and pentafluorosulfanyl containing (1,3,4-oxadiazol-2-yl)benzamides against drug-resistant Gram-positive bacteria." RSC Medicinal Chemistry 11, no. 1 (2020): 102–10. http://dx.doi.org/10.1039/c9md00391f.

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41

Syed, Tayyaba, Shahid Hameed, and Peter G. Jones. "(S)-N-{1-[5-(4-Chlorobenzylsulfanyl)-1,3,4-oxadiazol-2-yl]ethyl}-4-methylbenzenesulfonamide." Acta Crystallographica Section E Structure Reports Online 67, no. 10 (2011): o2793. http://dx.doi.org/10.1107/s1600536811039134.

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42

Verma, Vaijinath A., Anand R. Saundane, and Rajkumar S. Meti. "Synthesis of Schiff Base Indolyl-1,3,4-Oxadiazole, Thiazolidinone and Azetidinone as Efficient Antimicrobial, Antioxidant, Antituberculosis and Anticancer Agents." Asian Journal of Organic & Medicinal Chemistry 4, no. 2 (2019): 77–88. http://dx.doi.org/10.14233/ajomc.2019.ajomc-p175.

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The present investigation was under-taken to synthesize the Schiff base indole derivatives bearing of 1,3,4-oxadiazole thiazolidinone and azetidinone moieties. New series of 5-(5-substituted-3-phenyl-1H-indol-2-yl)-N-[(5-substituted-2-phenyl-1H-indol-3-yl)methylene]-1,3,4-oxadiazol-2-amines and screened their biological activities. Compound 4a showed excellent antibacterial and radical scavenging activities. Compound 5a revealed efficient to antifungal activity. In addition, compound 4a was found to be most active against H37Rv strain Mycobacterium tuberculosis. In case of anticancer activity

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43

Wang, Shu-Wen, Zheng-Quan Zuo, and Wen-Long Yang. "N,N-Dimethyl-4-[5-(5-methyl-1-phenyl-1H-pyrazol-4-yl)-1,3,4-oxadiazol-2-yl]aniline." Acta Crystallographica Section E Structure Reports Online 64, no. 2 (2008): o353. http://dx.doi.org/10.1107/s1600536807067402.

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44

Kapadiya, K., G. Dubal, Y. Bhola, and P. Dholaria. "Synthesis and Antimicrobial Evaluation of 1,3,4-Oxadiazole bearing Schiff Base Moiety." Asian Journal of Organic & Medicinal Chemistry 5, no. 1 (2020): 1–5. http://dx.doi.org/10.14233/ajomc.2020.ajomc-p199.

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A new series of 4-((5-(2-chlorophenyl)-1,3,4-oxadiazol-2-yl)methoxy)-N-(benzylidene derivatives)benzenamine (5a-k) have been synthesized and were screened for their in vitro antibacterial activity against Gram-positive bacteria (Pseudomonas aeruginosa, Streptococcus pyogenes), Gram-negative bacteria (Escherichia coli, Staphylococcus aureus) and antifungal activity (Candida albicans, Aspergillus niger, Aspergillus clavatus). Synthesized compounds were characterized by IR, mass (MS), 1H NMR and 13C NMR spectra. The synthesized compounds 5b, 5c, 5g and 5i showed potency in terms of antimicrobial

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45

Vachhani, Mukeshkumar, Jaydeep Lalpara, Sanjay Hadiyal, and Gaurang Dubal. "Microwave-assisted synthesis of bioactive tetrahydropyrimidine derivatives as antidiabetic agents." Folia Medica 64, no. 3 (2022): 478–87. http://dx.doi.org/10.3897/folmed.64.e62476.

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Abstract Introduction: In drug discovery, pyrimidine analogues show good biological response and many drug moieties have pyrimidine core. Aim: On the basis of prior review, we synthesized a series of N-(substituted phenyl)-1,3,6-trimethyl-4-(4-((5-(4-nitrophenyl)-1,3,4-oxadiazol-2-yl)methoxy)phenyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxamide parade a 1,3,4-oxadiazole core which were evaluated for in vitro antidiabetic screening. Materials and methods: The tetrahydropyrimidine derivatives have been synthesized by microwave irradiation method. It was carried out by Biginelli condensation o

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46

Zareef, Muhammad, Rashid Iqbal, Javid H. Zaidi, Muhammad Arfan, and Masood Parvez. "4-Methyl-N-[1-(5-thioxo-4,5-dihydro-1,3,4-oxadiazol-2-yl)propyl]benzenesulfonamide." Acta Crystallographica Section E Structure Reports Online 62, no. 6 (2006): o2481—o2483. http://dx.doi.org/10.1107/s1600536806018265.

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47

Stensland, Birgitta, and Ron J. Roberts. "N-(3-Methoxy-5-methylpyrazin-2-yl)-2-[4-(1,3,4-oxadiazol-2-yl)phenyl]pyridine-3-sulfonamide (ZD4054 Form 1)." Acta Crystallographica Section E Structure Reports Online 60, no. 10 (2004): o1817—o1819. http://dx.doi.org/10.1107/s1600536804022822.

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48

Rubab, Kaniz, Muhammad Athar Abbasi, Aziz-ur-Rehman, et al. "Convergent synthesis of new N -substituted 2-{[5-(1H -indol-3-ylmethyl)-1,3,4-oxadiazol-2-yl]sulfanyl}acetamides as suitable therapeutic agents." Brazilian Journal of Pharmaceutical Sciences 51, no. 4 (2015): 931–47. http://dx.doi.org/10.1590/s1984-82502015000400019.

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abstract A series of N-substituted 2-{[5-(1H-indol-3-ylmethyl)-1,3,4-oxadiazol-2-yl]sulfanyl}acetamides (8a-w) was synthesized in three steps. The first step involved the sequential conversion of 2-(1H-indol-3-yl)acetic acid (1) to ester (2) followed by hydrazide (3) formation and finally cyclization in the presence of CS2 and alcoholic KOH yielded 5-(1H-indole-3-yl-methyl)-1,3,4-oxadiazole-2-thiol (4). In the second step, aryl/aralkyl amines (5a-w) were reacted with 2-bromoacetyl bromide (6) in basic medium to yield 2-bromo-N-substituted acetamides (7a-w). In the third step, these electrophil

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49

Sharma, P., K. N. Subbulakshmi, B. Narayana, B. K. Sarojini, and R. Kant. "Crystal structure of 2-(thiophen-2-yl)-1-(5-thioxo-4,5-dihydro-1,3,4-oxadiazol-2-yl)ethenyl]benzamide : N,N-dimethylformamide (1 : 1)." Crystallography Reports 61, no. 2 (2016): 230–33. http://dx.doi.org/10.1134/s106377451602022x.

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50

Yin, Guo-Jie, Qing Zhang та Dong Li. "Tetrakis[μ3-4-nitro-N-(5-phenyl-1,3,4-oxadiazol-2-yl)benzamidato]tetrakis[methanolsodium(I)]". Acta Crystallographica Section E Structure Reports Online 68, № 5 (2012): m570. http://dx.doi.org/10.1107/s1600536812014791.

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