Notes

Synthesis and Antimicrobial Activity of 2-Substituted-phenyl-3-(N, N-dimethylformamido)-4-methyl-1,5-benzothiazepine

  • Xu Tongxiu ,
  • Wang Yan ,
  • Tian Keqing ,
  • Wang Ranran ,
  • Yan Jingyi ,
  • Zhang Ping
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  • a College of Chemistry and Materials Science, Hebei Normal University, Shijiazhuang 050024;
    b College of Life Science, Hebei Normal University, Shijiazhuang 050024;
    c Environment and Chemical Engineering, Hebei Chemical and Pharmaceutical College, Shijiazhuang 050026

Received date: 2018-04-16

  Revised date: 2018-05-31

  Online published: 2018-06-22

Supported by

Project supported by the Natural Science Foundation of Hebei Province (No. B2017205100).

Abstract

By introducing N,N-dimethylformamido into 1,5-benzothiazepine, 6 compounds of 2-substituted-phenyl-3-(N,N-dimethylformamido)-4-methyl-1,5-benzothiazepine 3a3f were designed and synthesized, Studies on the synthesis conditions of 3a3f revealed that 3a3f were dynamic control products. 3a3f had obvious inhibitory effect on fungi and bacteria especially for Cryptococcus neoformans and Escherichia coli.

Cite this article

Xu Tongxiu , Wang Yan , Tian Keqing , Wang Ranran , Yan Jingyi , Zhang Ping . Synthesis and Antimicrobial Activity of 2-Substituted-phenyl-3-(N, N-dimethylformamido)-4-methyl-1,5-benzothiazepine[J]. Chinese Journal of Organic Chemistry, 2018 , 38(10) : 2731 -2735 . DOI: 10.6023/cjoc201804029

References

[1] Tollefson, G. D.; Beasley, C. M.; Tamura, R. N.; Tran, P. V.; Potvin, J. H. Am. J. Psychiatry 1997, 154, 1248.
[2] Feighner, J. P.; Aden, G. C.; Fabre, L. F.; Rickers, K.; Smith, W. T. JAMA, J. Am. Med. Assoc. 1983, 249, 3057.
[3] Holopainen, I. E.; Kivela, R.; Korpi, E. R. Neurochem. Res. 2001, 26, 89.
[4] Chaffmann, M.; Brogden, R. N. Drugs 1985, 29, 387.
[5] Nagao, T.; Stao, M.; Iwasawa, Y.; Takada, T.; Ishida, R.; Nakajima, H.; Kiyomoto, A. Jpn. J. Pharmacol. 1972, 22, 467.
[6] Kawakita, S.; Kinoshita, M.; Ishikawa, H.; Kagoshima, T.; Katori, R.; Ishikawa, K.; Hirota, Y. Clin. Cardiol. 1991, 14, 53.
[7] Tarabova, B.; Lacinova, L.; Engel, J. Eur. J. Pharmacol. 2007, 573, 39.
[8] Karthikeyan, S. V.; Perumal, S. Tetrahedron Lett. 2007, 48, 2261.
[9] Urbanski, M. J.; Chen, R. H.; Demarest, K. T.; Gunnet, J.; Look, R.; Ericson, E.; Murray, W. V.; Rybczynski, P. J.; Zhang, X. Y. Bioorg. Med. Chem. Lett. 2003, 13, 4031.
[10] Ni, W.; Zhou, H. P.; Xiang, G. Y.; Huang, S. T.; Dai, C. Herald Med. 2010, 29, 342(in Chinese). (倪尉, 周和平, 项光亚, 黄胜堂, 戴畅, 医药导报, 2010, 29, 342.)
[11] Garg, N.; Chandra, T.; Archana; Jain, A. B.; Kumar, A. Eur. J. Med. Chem. 2010, 45, 1529.
[12] Wang, H.; Li, M. L.; Qi, Y.; Xue, Y. P. Heilongjiang Med. J. 2006, 19, 213(in Chinese). (王华, 李明兰, 齐洋, 薛雨鹏, 黑龙江医药, 2006, 19, 213.)
[13] Kawakami, M.; Matsumura, S.; Shimamura, T.; Iwasaki, T.; Furukawa, H.; Matsunaga, K.; Yonetani, Y.; Iwaki, K. J. Cardiovasc. Pharm. 1996, 28, 695.
[14] Kurokawa, J.; Adachi-Akahane, S.; Nagao, T. Eur. J. Pharm. 1997, 325, 229.
[15] Jawahar, L.; Mehta, M. D. Am. J. Cardiol. 1994, 73, A18.
[16] Amdrogi, V.; Furlani, A.; Grandolini, G.; Papaioannou, A.; Perioli, L.; Scarcia, V.; Tuttobello, L. Eur. J. Med. Chem. 1993, 28, 659.
[17] Tan, K. Q.; Liu, X. X.; Xue, Z. Q.; Yang, T.; Du, X. Q.; Zhang, P. Chin. J. Org. Chem. 2013, 33, 2237(in Chinese). (田克情, 刘晓欣, 薛子桥, 杨田, 杜星琼, 张萍, 有机化学, 2013, 33, 2237.)
[18] Wu, Y. Y.; Tan, K. Q.; Yang, T.; Du, X. Q.; Zhang, P. Chin. J. Org. Chem. 2013, 33, 1465(in Chinese). (武云云, 田克情, 杨田, 杜星琼, 张萍, 有机化学, 2013, 33, 1465.)
[19] Zhang, P.; Xuan, Y.; Liu, W.; Li, Y. Chin. J. Org. Chem. 2011, 31, 1240(in Chinese). (张萍, 宣烨, 刘薇, 李媛, 有机化学, 2011, 31, 1240.)
[20] Li, W. H.; Lan, J. M.; Li, C.; Cao, Y. T.; Wang, H. B.; Wang, L. Z.; Zhang, P.; Wang, Y. X.; Li, Y. Acta Chim. Sinica 2009, 67, 2732(in Chinese). (李文红, 兰佳明, 李成, 曹云涛, 王海波, 王兰芝, 张萍, 王永祥, 李媛, 化学学报, 2009, 67, 2732.)
[21] Zhang, J.; Mu, B. S.; Wu, M.; Bian, Y. Q.; Li Y.Chem. J. Chin. Univ. 2015, 36, 687(in Chinese). (张静, 穆博帅, 吴萌, 边艳青, 李媛, 高等学校化学学报, 2015, 36, 687.)
[22] Chris, D. S.; Gregory, R.; Leo, M.; Robert, A. B. J. Org. Chem. 2010, 75, 4716.

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