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Synthesis of novel 1,3,4-oxadiazole derivatives as potential antimicrobial agents.
Acta Pol Pharm. 2010 May-Jun; 67(3):247-53.AP

Abstract

Some new 3-acetyl-5-(3-chloro-1-benzo[b]thiophen-2-yl)-2-substituted phenyl-2,3-dihydro-1,3,4-oxadiazoles and 2-(3-chloro-1-benzo[b]thiophen-2-yl)-5-substituted phenyl-1,3,4-oxadiazoles have been synthesized and evaluated for antimicrobial activity. Initially, 3-chloro-1-benzo[b]thiophene-2-carbonyl chloride (1) was prepared from cinnamic acid in the presence of chlorobenzene and thionyl chloride. This compound (1) was treated with hydrazine hydrate to afford 3-chloro-1-benzo[b]thiophene-2-carbohydrazine (2) which was further reacted with various aromatic aldehydes to yield hydrazones (3a-h). Further reaction of these hydrazones (3a-h) with acetic anhydride gave 3-acetyl-5-(3-chloro-1-benzo[b]thiophen-2-yl)-2-substituted phenyl-2,3-dihydro-1,3,4-oxadiazoles (4a-h). Reaction of the same compounds (3a-h) in the presence of chloramine-T afforded 2-(3-chloro-1-benzo[b]thiophen-2-yl)-5-substituted phenyl-1,3,4-oxadiazoles (5a-h). The structures of newly synthesized compounds (4a-h) and (5a-h) have been confirmed by spectroscopic techniques such as IR, 1H NMR and elemental analysis. All the compounds were screened for their antibacterial activities against Staphylococcus aureus, Bacillus subtilis. Escherichia coli and Pseudomonas aeruginosa and for antifungal activity against Candida albicans and Asperigillus niger. The compounds exhibited significant antibacterial and moderate antifungal activities. Compounds 4c and 4e were found to be most potent with activities, even better than standard drug ciprofloxacin against S. aureus and B. subtilis.

Authors+Show Affiliations

Department of Pharmaceutical Chemistry, S.D.College of Pharmacy, Barnala-148 101, India. rchawlapharma@yahoo.comNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article

Language

eng

PubMed ID

20524426

Citation

Chawla, Rakesh, et al. "Synthesis of Novel 1,3,4-oxadiazole Derivatives as Potential Antimicrobial Agents." Acta Poloniae Pharmaceutica, vol. 67, no. 3, 2010, pp. 247-53.
Chawla R, Arora A, Parameswaran MK, et al. Synthesis of novel 1,3,4-oxadiazole derivatives as potential antimicrobial agents. Acta Pol Pharm. 2010;67(3):247-53.
Chawla, R., Arora, A., Parameswaran, M. K., Chan, P., Sharma, D., Michael, S., & Ravi, T. K. (2010). Synthesis of novel 1,3,4-oxadiazole derivatives as potential antimicrobial agents. Acta Poloniae Pharmaceutica, 67(3), 247-53.
Chawla R, et al. Synthesis of Novel 1,3,4-oxadiazole Derivatives as Potential Antimicrobial Agents. Acta Pol Pharm. 2010 May-Jun;67(3):247-53. PubMed PMID: 20524426.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Synthesis of novel 1,3,4-oxadiazole derivatives as potential antimicrobial agents. AU - Chawla,Rakesh, AU - Arora,Anshu, AU - Parameswaran,Manoj Kumar, AU - Chan,Prabodh, AU - Sharma,Der, AU - Michael,Sukumar, AU - Ravi,Thengungal Kochupappy, PY - 2010/6/8/entrez PY - 2010/6/9/pubmed PY - 2010/6/25/medline SP - 247 EP - 53 JF - Acta poloniae pharmaceutica JO - Acta Pol Pharm VL - 67 IS - 3 N2 - Some new 3-acetyl-5-(3-chloro-1-benzo[b]thiophen-2-yl)-2-substituted phenyl-2,3-dihydro-1,3,4-oxadiazoles and 2-(3-chloro-1-benzo[b]thiophen-2-yl)-5-substituted phenyl-1,3,4-oxadiazoles have been synthesized and evaluated for antimicrobial activity. Initially, 3-chloro-1-benzo[b]thiophene-2-carbonyl chloride (1) was prepared from cinnamic acid in the presence of chlorobenzene and thionyl chloride. This compound (1) was treated with hydrazine hydrate to afford 3-chloro-1-benzo[b]thiophene-2-carbohydrazine (2) which was further reacted with various aromatic aldehydes to yield hydrazones (3a-h). Further reaction of these hydrazones (3a-h) with acetic anhydride gave 3-acetyl-5-(3-chloro-1-benzo[b]thiophen-2-yl)-2-substituted phenyl-2,3-dihydro-1,3,4-oxadiazoles (4a-h). Reaction of the same compounds (3a-h) in the presence of chloramine-T afforded 2-(3-chloro-1-benzo[b]thiophen-2-yl)-5-substituted phenyl-1,3,4-oxadiazoles (5a-h). The structures of newly synthesized compounds (4a-h) and (5a-h) have been confirmed by spectroscopic techniques such as IR, 1H NMR and elemental analysis. All the compounds were screened for their antibacterial activities against Staphylococcus aureus, Bacillus subtilis. Escherichia coli and Pseudomonas aeruginosa and for antifungal activity against Candida albicans and Asperigillus niger. The compounds exhibited significant antibacterial and moderate antifungal activities. Compounds 4c and 4e were found to be most potent with activities, even better than standard drug ciprofloxacin against S. aureus and B. subtilis. SN - 0001-6837 UR - https://www.unboundmedicine.com/medline/citation/20524426/Synthesis_of_novel_134_oxadiazole_derivatives_as_potential_antimicrobial_agents_ L2 - http://www.ptfarm.pl/pub/File/Acta_Poloniae/2010/3/247.pdf DB - PRIME DP - Unbound Medicine ER -