全部 标题 作者
关键词 摘要

OALib Journal期刊
ISSN: 2333-9721
费用:99美元

查看量下载量

相关文章

更多...

Microwave-Assisted Synthesis of Some 1,3,4-Oxadiazole Derivatives and Evaluation of Their Antibacterial and Antifungal Activity

DOI: 10.1155/2014/694060

Full-Text   Cite this paper   Add to My Lib

Abstract:

A series of substituted 1,3,4-oxadiazole derivatives (3a–f) and (6a–f) have been synthesized from diphenylacetic acid hydrazide under microwave irradiation in various reaction conditions. The structures of the synthesized compounds were assigned on the basis of elemental analysis, IR, and 1H NMR. These targeted compounds have been tested for their antibacterial and antifungal activities compared to ampicillin and griseofulvin as standard drug. Compounds 3a, 3e, 3f, 6c, 6d, 6e, and 6d exhibited the maximum antibacterial activities while 3b, 3c, 3d, 3e, 6a, 6d, and 6e exhibited the maximum antifungal activities. 1. Introduction Oxadiazole has occupied a unique place in the field of medicinal and pesticide chemistry due to its wide range of activities. Bhandari et al. [1] have reported the design, synthesis, and evaluation of anti-inflammatory, analgesic, and ulcerogenicity of novel S-substituted phenacyl-1,3,4-oxadiazole-2-thiol and Schiff bases of diclofenac acid as nonulcerogenic derivatives whereas Narayana et al. [2] have synthesized some new 2-(6-methoxy-2-naphthyl)-5-aryl-1,3,4-oxadiazoles as possible nonsteroidal anti-inflammatory and analgesic agents. Synthesis and evaluation of anti-inflammatory, analgesic, ulcerogenic, and lipid peroxidation properties of ibuprofen derivatives have been studied by Amir and Kumar [3] while Hui et al. [4] have carried out the synthesis and antibacterial activities of 1,3,4-oxadiazole derivatives containing 5-methylisoxazole moiety. 1,3,4-Oxadiazole derivatives have been synthesized by ?ahin et al. [5] and they have also studied their antifungal activity. Novel chiral and achiral benzenesulfonamides bearing 1,3,4-oxadiazole moieties have been synthesized by Zareef et al. [6] and studied for their antimalarial activity. Husain and Ajmal [7] have synthesized novel 1,3,4-oxadiazole derivatives and investigated their anticonvulsant properties. Burbuliene et al. [8] have reported the synthesis and anti-inflammatory activity of derivatives of 5-[(2-disubstituted amino-6-methylpyrimidin-4-yl)-sulfanylmethyl]-3H-1,3,4-oxadiazole-2-thiones while Padmaja et al. [9] have studied the synthesis and antioxidant activity of disubstituted 1,3,4-oxadiazole, 1,3,4-thiadiazoles, and 1,2,4-triazoles. El-Emam et al. [10] have synthesized certain 5-(1-adamantyl)-2-substitutedthio-1-3-4-oxadiazoles and 5-(1-adamantyl)-3-substituted aminomethyl-1,3,4-oxadiazoline-2-thiones and studied their anti-HIV-1 activity whereas synthesis and antitumor activity of some new 1,3,4-oxadiazole, pyrazole, and pyrazolo[3,4-d]pyrimidine derivatives

References

[1]  S. V. Bhandari, K. G. Bothara, M. K. Raut, A. A. Patil, A. P. Sarkate, and V. J. Mokale, “Design, synthesis and evaluation of anti-inflammatory, analgesic and ulcerogenicity studies of novel S-substituted phenacyl-1,3,4-oxadiazole-2-thiol and Schiff bases of diclofenac acid as nonulcerogenic derivatives,” Bioorganic and Medicinal Chemistry, vol. 16, no. 4, pp. 1822–1831, 2008.
[2]  B. Narayana, K. K. V. Raj, B. V. Ashalatha, and N. S. Kumari, “Synthesis of some new 2-(6-methoxy-2-naphthyl)-5-aryl-1,3,4-oxadiazoles as possible non-steroidal anti-inflammatory and analgesic agents,” Archiv der Pharmazie, vol. 338, no. 8, pp. 373–377, 2005.
[3]  M. Amir and S. Kumar, “Synthesis and evaluation of anti-inflammatory, analgesic, ulcerogenic and lipid peroxidation properties of ibuprofen derivatives,” Acta Pharmaceutica, vol. 57, no. 1, pp. 31–45, 2007.
[4]  X.-P. Hui, C.-H. Chu, Z.-Y. Zhang, Q. Wang, and Q. Zhang, “Synthesis and antibacterial activities of 1,3,4-oxadiazole derivatives containing 5-methylisoxazole moiety,” Indian Journal of Chemistry B, vol. 41, no. 10, pp. 2176–2179, 2002.
[5]  G. ?ahin, E. Palaska, M. Ekizo?lu, and M. ?zalp, “Synthesis and antimicrobial activity of some 1,3,4-oxadiazole derivatives,” Farmaco, vol. 57, no. 7, pp. 539–542, 2002.
[6]  M. Zareef, R. Iqbal, N. G. De Dominguez et al., “Synthesis and antimalarial activity of novel chiral and achiral benzenesulfonamides bearing 1,3,4-oxadiazole moieties,” Journal of Enzyme Inhibition and Medicinal Chemistry, vol. 22, no. 3, pp. 301–308, 2007.
[7]  A. Husain and M. Ajmal, “Synthesis of novel 1,3,4-oxadiazole derivatives and their biological properties,” Acta Pharmaceutica, vol. 59, no. 2, pp. 223–233, 2009.
[8]  M. M. Burbuliene, V. Jakubkiene, G. Mekuskiene, E. Udrenaite, R. Smicius, and P. Vainilavicius, “Synthesis and anti-inflammatory activity of derivatives of 5-[(2-disubstitutedamino-6-methyl-pyrimidin-4-yl)-sulfanylmethyl]-3H-1,3, 4-oxadiazole-2-thiones,” Farmaco, vol. 59, no. 10, pp. 767–774, 2004.
[9]  A. Padmaja, C. Rajasekhar, A. Muralikrishna, and V. Padmavathi, “Synthesis and antioxidant activity of disubstituted 1,3,4-oxadiazole, 1,3,4-thiadiazoles and 1,2,4-triazoles,” Journal of Chemical and Pharmaceutical Research, vol. 4, no. 1, pp. 294–302, 2012.
[10]  A. A. El-Emam, O. A. Al-Deeb, M. Al-Omar, and J. Lehmann, “Synthesis, antimicrobial, and anti-HIV-1 activity of certain 5-(1-adamantyl)-2-substituted thio-1,3,4-oxadiazoles and 5-(1-adamantyl)-3-substituted aminomethyl-1,3,4-oxadiazoline-2-thiones,” Bioorganic and Medicinal Chemistry, vol. 12, no. 19, pp. 5107–5113, 2004.
[11]  W. S. El-Hamouly, K. M. Amin, S. A. El-Assaly, and E. A. A. El-Meguid, “Synthesis and antitumor activity of some new 1,3,4-oxadiazole, pyrazole and pyrazolo [3,4-d]pyrimidine derivatives attached to 4-benzothiazol-2-yl phenyl moiety,” Der Pharma Chemica, vol. 3, no. 6, pp. 282–292, 2011.
[12]  T. W. Newton, “Herbicidal[1, 3, 4]oxadiazoles and thiadiazoles,” US 5591695 A, 1997.
[13]  N. Solak and S. Rollas, “Synthesis and antituberculosis activity of 2-(aryl/alkylamino)-5-(4-aminophenyl)-1,3,4-thiadiazoles and their Schiff bases,” Arkivoc, vol. 2006, no. 12, pp. 173–181, 2006.
[14]  J. Matysiak, A. Nasulewicz, M. Pe?czyńska, M. ?witalska, I. Jaroszewicz, and A. Opolski, “Synthesis and antiproliferative activity of some 5-substituted 2-(2,4-dihydroxyphenyl)-1,3,4-thiadiazoles,” European Journal of Medicinal Chemistry, vol. 41, no. 4, pp. 475–482, 2006.
[15]  B. S. Holla, B. S. Rao, R. Gonsalves, B. K. Sarojini, and K. Shridhara, “Synthesis of some new biologically active thiadiazolotriazinones. Part III,” Farmaco, vol. 57, no. 8, pp. 693–696, 2002.
[16]  M. Radi, E. Crespan, G. Botta et al., “Discovery and SAR of 1,3,4-thiadiazole derivatives as potent Abl tyrosine kinase inhibitors and cytodifferentiating agents,” Bioorganic and Medicinal Chemistry Letters, vol. 18, no. 3, pp. 1207–1211, 2008.
[17]  National Committee for Clinical Laboratory Standard, “Reference method for broth dilution antifungal susceptibility testing of yeasts,” Approved Standard M27A, NCCLS, Wayne, Pa, USA, 1997.

Full-Text

comments powered by Disqus

Contact Us

service@oalib.com

QQ:3279437679

WhatsApp +8615387084133