Synthesis and Antibacterial Activity of 5-(2-Hydroxyphenyl)-1,3,4- thiadiazol-2-yl-sulfanyl Acetyl Hydrazones

doi:10.6023/cjoc201206013

Chin. J. Org. Chem. ›› 2013, Vol. 33 ›› Issue (01): 154-158.DOI: 10.6023/cjoc201206013 Previous Articles Next Articles

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5-(2-羟基苯基)-1,3,4-噻二唑-2-硫基乙酰腙化合物的合成及抑菌活性

王应红, 杨录, 刘志昌

乐山师范学院化学学院乐山 614000

收稿日期:2012-06-12 修回日期:2012-10-08 发布日期:2012-10-12
通讯作者: 刘志昌 E-mail:liu_zhichang04@163.com
基金资助:
四川省科技厅应用基础(No. 2010JY0148)和四川省乐山市科技局重点(No. 08SZD092)资助项目

Synthesis and Antibacterial Activity of 5-(2-Hydroxyphenyl)-1,3,4- thiadiazol-2-yl-sulfanyl Acetyl Hydrazones

Wang Yinghong, Yang Lu, Liu Zhichang

Department of Chemistry, Leshan Normal University, Leshan 614000

Received:2012-06-12 Revised:2012-10-08 Published:2012-10-12
Supported by:
Project supported by the Application of Basic Project of the Science and Technology Agency of Sichuan Province (No. 2010JY0148) and the Key Projects of the Science and the Technology Bureau of Leshan City in Sichuan Province (No. 08SZD092).

A series of 5-(2-hydroxyphenyl)-1,3,4-thiadiazol-2-yl-sulfanyl acetyl hydrazones were synthesized with 2-mercapto-5-(2-hydroxyphenyl)-1,3,4-thiadiazole as starting material, followed by thioetherification, hydrazide reaction and hydrazone reaction. The structures of these compounds were characterized by ¹H NMR, ¹³C NMR, IR, MS techniques and elemental analysis. The antimicrobial activities of these compounds were also originally studied. The results showed that most of these compounds have potent antibacterial activities. These compounds of aromatic aldehyde-5-(2-hydroxyphen-yl)-1,3,4- thiadiazol-2-yl-sulfanyl acetyl hydrazone (4a～4h) showed better antibacterial activities than 2-butenal-5-(2-hydroxyphenyl)-1,3,4-thiadiazol-2-yl-sulfanyl acetyl hydrazone (4i).

Key words: 2-mercapto-5-(2-hydroxyphenyl)-1,3,4-thiadiazole, acyl hydrazones, synthesis, antibacterial activity

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Wang Yinghong, Yang Lu, Liu Zhichang. Synthesis and Antibacterial Activity of 5-(2-Hydroxyphenyl)-1,3,4- thiadiazol-2-yl-sulfanyl Acetyl Hydrazones[J]. Chin. J. Org. Chem., 2013, 33(01): 154-158.

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[1] Foroumadi, A.; Mansouri, S.; Kiani, Z.; Rahmani. A. Eur. J. Med. Chem. 2003, 38,851.

[2] Cheng, J.; Liu, F.; Song, B-A.;Yang, S.; Hu, D.-Y.; Jin, L.-H.; Chen, Z.; Xue, W. Chin. J. Org. Chem. 2008, 28, 894 (in Chinese). (陈江, 刘芳, 宋宝安, 杨松, 胡德禹, 金林红, 陈卓, 薛伟, 有机化学, 2008, 28, 894.)

[3] Dimmock, J. R.; Vashishtha, S. C.; Stables, J. P. Eur. J. Med. Chem. 2000, 35, 241.

[4] Telvekar,V. N.; Belubbi, A.; Bairwa, V. K.; Satardekar, K. Bioorg. Med. Chem. Lett. 2012, 22, 2343.

[5] Himmel, D. M.; Sarafianos, S. G.; Dharmasena, S.; Hossain, M. M.; Simandle, K. M.; Ilina, T.; Jr, A. C.; Knight, J. L.; Julias, J. G.; Clark, P. K.; Jespersen, K. K.; Levy, R. M.; Hughes, S. H.; Parniak, M. A.; Arnold, E. ACS Chem. Biol. 2006, 15, 702.

[6] Kalinowskl, D. A.; Richardson, E. D. Pharmacol. Rev. 2005, 57, 547.

[7] Lovejoy, D. B.; Richardson, D. R. Blood 2002, 100, 666.

[8] Richardson, D. R.; Kalinowski, D. S.; Lau, S.; Jansson, P. J.; Lovejoy, D. B. Biochim. Biophys. Acta, Gen Subj. 2009, 1790, 702.

[9] Kalinowski, D. S.; Yu, Y.; Sharpe, P. C.; Islam, M.; Liao, Y. T.; Lovejoy, D. B.; Kumar, N.; Bernhardt, P. V.; Richardson, D. R. J. Med. Chem. 2007, 50, 3716.

[10] Melnyk, P.; Leroux, V.; Sergheraerta, C.; Grellier, P. Bioorg. Med. Chem. Lett. 2006, 16, 31.

[11] Rollas, S.; Küçükgüzel, G. Molecules 2007, 12, 1910.

[12] Foroumadi, A.; Mansouri, S.; Kiani, Z.; Rahmani, A. Eur. J. Med. Chem. 2003, 38, 851.

[13] Thomasco, L. M.; Gadwood, R. C.; Weaver, E. A.; Ochoada, J. M.; Ford, C. W.; Zurenko, G. E.; Hamel, J. C.; Stapert, D.; Moerman, J. K.; Schaadt, R. D.; Yagi, B. H. Bioorg. Med. Chem. Lett. 2003, 13, 4193.

[14] Karakus. S.; Rollas, S. Farmaco 2002, 57, 577.

[15] Schenone, S.; Brullo, C.; Bruno, O.; Bondavalli, F.; Ranise, A.; Filippelli, W.; Rinaldi, B.; Capuanob, A.; Falcone, G. Bioorg. Med. Chem. 2006, 14, 1698

[16] Palaska, E.; Sahin, G.; Kelicen, P.; Durlu, N. T.; Altinok G. Farmaco 2002, 57, 101.

[17] Terzioglu, N.; Gürsoy, A. Eur. J. Med. Chem. 2003, 38, 781.

[18] Liu, Z.-C.; Liu, X.-X.; Wang, Y.-H.; Yang, L. Chin. J. Org. Chem. 2011, 31, 136 (in Chinese). (刘志昌, 刘晓霞, 王应红, 杨录, 有机化学, 2011, 31, 136.)

[19] Zhu, S.-S.; Lu, J.-R.; Xin, C.-W.; Lu, B.-W.; Bao, X.-R.; Tang, D.-W.; Zou, M.; Liu, Q. Chin. J. Org.Chem. 2010, 30, 1914 (in Chinese). (朱姗姗, 卢俊瑞, 辛春伟, 卢博为, 鲍秀荣, 唐大伟, 邹敏, 刘倩, 有机化学, 2010, 30, 1914.)

[20] Li, Y.-L. Clinical Microbiology and Inspection, People’s Health Press, Beijing, 1995, p. 77 (in Chinese). (李影林, 临床微生物学及检验, 人民卫生出版社, 北京, 1995, p. 77.)

5-(2-羟基苯基)-1,3,4-噻二唑-2-硫基乙酰腙化合物的合成及抑菌活性

Synthesis and Antibacterial Activity of 5-(2-Hydroxyphenyl)-1,3,4- thiadiazol-2-yl-sulfanyl Acetyl Hydrazones

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