Chinese Journal of Organic Chemistry >
Synthesis and Antibacterial Activities of Novel S-β-D-Glucosides of 1,2,4-Triazole
Received date: 2014-10-15
Revised date: 2014-11-19
Online published: 2014-12-09
Supported by
Project supported by the National Natural Science Foundation of China (Nos. 21176194, 21476174).
A series potassiums 3 were prepared by substituted benzoyl hydrazide 2 and CS2 in potassium hydroxide. These compounds 3 were converted to 4-amino-5-substituted phenyl-3-ylsulfanyl-4H-1,2,4-triazols (4) by cyclization in hydrazine hydrate. Nine novel S-β-D-glucosides (5a～5i) were synthesized by glycosylation of 4 and bromo-2,3,4,6-tetra-O-acetyl- α-D-glucopyranoside in the presence of potassium hydroxide with acetone as solvent. The structures of all target compounds were confirmed by 1H NMR, 13C NMR, IR and HRMS spectrum. The results of preliminary bioassay show that most of the tested compounds displayed variable inhibitory activity against Escherichia coli, Staphylococcus aureus, Bacillus subtilis and Monilia albican. Especially, compound 5g has strong antibacterial activity with minimum inhibitory concentration values of 8, 16, 64, 2 μg/mL against four tested strains respectively which are similar to or higher than those of the controlled drug fluconazole or triclosan. The interaction and binding free energy of the target compounds 5a～5i with FabI were studied by Autodock Vina.
Zhang Ruibo , Lu Junrui , Xin Chunwei , Liu Jinbiao , Mu Jiangbei , Yang Xuyun , Wang Hongyun , Wang Meijun , Zhang He . Synthesis and Antibacterial Activities of Novel S-β-D-Glucosides of 1,2,4-Triazole[J]. Chinese Journal of Organic Chemistry, 2015 , 35(4) : 858 -864 . DOI: 10.6023/cjoc201410021
[1] Yang, B. Ph.D. Dissertation, Ocean University of China, Qingdao, 2005 (in Chinese).
(杨波, 博士论文, 中国海洋大学, 青岛, 2005.)
[2] E1 Ashry, E. S. H.; E1 Tamany, E. S. H.; E1 Fattah, M. E. D. A.; Boraei, A. T. A.; Abd E1-Nabi, H. M. Eur. J. Med. Chem. 2013, 66, 106.
[3] Sumangala, V.; Poojary, B.; Chidananda, N.; Arulmoli, T. Eur. J. Med. Chem. 2012, 54, 59.
[4] Prasad, D. J.; Ashok, M.; Karegoudar, P.; Poojary, B.; Holla, B. S.; Kumari, N. S. Eur. J. Med. Chem. 2009, 44, 551. [5] Turan-Zitouni, G.; Kaplanc?kl?, Z. A.; Y?ld?z, M. T.; Chevallet, P.; Kaya, D. Eur. J. Med. Chem. 2005, 40, 607.
[6] Shavarama, H. B.; Narayana, P. K.; Sooryanarayana, R. B.; Shivananda, M. K. Eur. J. Med. Chem. 2002, 37, 511.
[7] Mavrova, A. T.; Wesselinova, D.; Tsenov, Y. A.; Denkova, P. Eur. J. Med. Chem. 2009, 44, 63.
[8] Feng, C. T.; Wang, L. D. Med. Chem. Res. 2012, 21, 315.
[9] Bakr, F.; Wahab, A.; Abdel-Latif, E.; Mohameda, H. A. Eur. J. Med. Chem. 2012, 52, 263.
[10] Almasirad, S. A.; Tabatabai, M.; Faizi, A.; Kebriaeezadeh, N.; Mehrabi, A.; Dalvandi, A. S. Bioorg Med. Chem. Lett. 2004, 14, 6057.
[11] Amir, M.; Shikha, K. Eur. J. Med. Chem. 2004, 39, 535.
[12] Mu, M. M.; Lu, B. W.; Lu, J. R.; Xin, C. W.; Ji, D. Chin. J. Org. Chem. 2012, 32, 1101 (in Chinese).
(穆曼曼, 卢博为, 卢俊瑞, 辛春伟, 戢丹, 有机化学, 2012, 32, 1101.)
[13] Levy, C. W.; Roujeinikova, A.; Sedelnikova, S.; Baker, P. J.; Stuitje, A. R.; Slabas, A. R.; Rice, D. W.; Rafferty, J. B. Nature 1999, 398(6726), 383.
[14] Zhu, S.-S.; Lu, J.-R.; Xin, C.-W.; Lu, B. W.; Bao, X. R.; Zou, M.; Liu, Q. Chem. J. Chin. Univ. 2010, 31, 2228 (in Chinese).
(朱姗姗, 卢俊瑞, 辛春伟, 卢博为, 鲍秀荣, 邹敏, 刘倩, 高等学校化学学报, 2010, 31, 2228.)
[15] Ji, D.; Lu, J. R.; Lu, B. W.; Xin, C. W.; Peng, C. Y.; Bao, X. R. Bioorg. Med. Chem. Lett. 2013, 23, 1997.
[16] Varki, A. Glycobiology 1993, 3, 97.
[17] Ji, D.; Lu, J. R.; Xin, C. W.; Peng, C. Y.; Mu, J. B. Chin. J. Org. Chem. 2013, 33, 1062 (in Chinese).
(戢丹, 卢俊瑞, 辛春伟, 彭春勇, 穆江蓓, 有机化学, 2013, 33, 1062.)
[18] Ai, Y. X., Lu, J. R.; Xin, C. W.; Mu J. B.; Yang, X. Y.; Zhang, H. Acta Phys.-Chim. Sin. 2014, 30, 559 (in Chinese).
(艾义新, 卢俊瑞, 辛春伟, 穆江蓓, 杨旭云, 张贺, 物理化学学报, 2014, 30, 559.)
[19] Andresas, K. Molecular Modeling of Proteins, Totowa, NJ, 2008, p. 371.
[20] Ai, Y. X. M.S. Thesis, Tianjin University of Technolgy, Tianjin, 2014 (in Chinese)
(艾义新, 硕士论文, 天津理工大学, 天津, 2014).
[21] Mark, J. B.; Claire, A. T.; Joanne, E. Org. Lett. 2013, 15, 2430.
[22] Arul, K.; Anto, A. Int. J. Clin. Pharm-net. 2014, 6, 213.
[23] Wang, X.Y.; Wang, H.; Chen, P. Y.; Pang, Y. P.; Zhao, Z. L.; Wu, Z.C. J. Chem. 2014.
[24] Li, W. H. CN 102329273, 2012 [Chem. Abstr. 2012, 156, 230657].
[25] Dilipkumar, P.; Vipul, S.; Pandey, D. D.; Maurya, R. K. Int. J. Clin. Pharm-net. 2014, 6, 213.
[26] Lakshman,A. B.; Gupta, R. L. Asian J. Chem. 2009, 21, 86.
[27] An, Y.; Zhang, T.; Jiang, H.; Zhang, L.; Han, J.; Yao, M. X. Chin. J. Org. Chem. 2012, 32, 1308 (in Chinese).
(安悦, 张婷, 姜华, 张琳, 韩杰, 姚明星, 有机化学, 2012, 32, 1308.)
[28] Lakshman, A. B.; Gupta, R. L. Asian J. Chem. 2009, 21, 86.
[29] Wang, X. Q.; Zhao, Z. G.; Li, W. J.; Liu, X. L.; Han, T. Chin. J. Org. Chem. 2010, 30, 764 (in Chinese).
(王晓庆, 赵志刚, 李伟杰, 刘兴利, 韩涛, 有机化学, 2010, 30, 764.)
/
| 〈 |
|
〉 |
