Citation: Wang Ranran, Wang Yan, Bian Yanqing, Zhang Ping. Synthesis and Antifungal Activity of 1, 5-Benzothiazepines Containing 1, 2, 3-Triazole[J]. Chinese Journal of Organic Chemistry, ;2020, 40(2): 398-407. doi: 10.6023/cjoc201907056 shu

Synthesis and Antifungal Activity of 1, 5-Benzothiazepines Containing 1, 2, 3-Triazole

a.
College of Chemistry and Materials Science, Hebei Normal University, Shijiazhuang 050024
b.
College of Life Science, Hebei Normal University, Shijiazhuang 050024

Corresponding author: Zhang Ping, zhangpingp@sina.com
Received Date: 31 July 2019
Revised Date: 5 October 2019
Available Online: 25 February 2019
Fund Project: the Natural Science Foundation of Hebei Province B2017205100Project supported by the Natural Science Foundation of Hebei Province (No. B2017205100)

Figures(2)

Three kinds of 1, 5-benzothiazepines containing 1, 2, 3-triazole, 3-(1H-1, 2, 3-triazolyl)-4-aryl-2, 5-dihydro-1, 5-benzo-thiazepines (5a~5f), 3-(2H-1, 2, 3-triazolyl)-4-aryl-2, 3-dihydro-1, 5-benzothiazepines (6a~6f) and 3-(1H-1, 2, 3-triazolyl)-4-aryl-2, 3, 4, 5-tetrahydro-1, 5-benzothiazepines (7a~7f), were designed and synthesized. The synthesis conditions of intermediates and target products were studied. Two by-products were separated and their structures were determined. The antifungal activity test of the target products showed that compounds 5a~5f exhibited high inhibitory effects against fungi especially for Cryptococcus neoformans. The preliminary study on the structure-activity relationship of antifungal activity reveled that 1H-1, 2, 3-triazolyl and C=C double bond were the key function groups in the antifungal activity of 5a~5f.
- 1, 5-benzothiazepine,
- 1, 2, 3-triazole,
- antifungal activity,
- structure-activity relationship
1. [1]
  Balaban, A. T.; Oniciu, D. C.; Katritzky, A. R. Chem. Rev. 2004, 104, 2777. doi: 10.1021/cr0306790
2. [2]
  Zhao, Y. L.; He, S. Q.; Xu, C. D. Introduction to Heterocyclic Chemistry, Higher Education Press, Beijing, 1992, p. 13(in Chinese).
3. [3]
  Giller, S. A.; Zaeva, S. P.; Venter, K. K.; Alekseeva, L. N.; Kruzmetra, L. V.; Germane, S. K. Chem. Heterocycl. Compd. 1965, 1, 122.
4. [4]
  Liao, Y.; Bastiaan, J. V.; Nienke, R.; Wia, T.; Hakan, W. J. Med. Chem. 1999, 42, 2235. doi: 10.1021/jm991005d
5. [5]
  Xu, T. X.; Wang, Y.; Tian, K. Q.; Wang, R. R.; Yan, J. Y.; Zhang, P. Chin. J. Org. Chem. 2018, 38, 2731(in Chinese).
6. [6]
  Sarro, G. D.; Chimirri, A.; Sarro, A. D.; Gitto, R.; Grasso, S.; Zappala, M. Eur. J. Med. Chem. 1995, 30, 925. doi: 10.1016/0223-5234(96)88311-5
7. [7]
  Karnail, S. A.; James, L. B.; Anders, H.; Suzanne, M. J. Med. Chem. 1987, 30, 635. doi: 10.1021/jm00387a009
8. [8]
  Chaffmann, M.; Brogden, R. N. Drugs 1985, 29, 387 doi: 10.2165/00003495-198529050-00001
9. [9]
  Kawakita, S.; Kinoshita, M.; Ishikawa, H.; Kagoshima, T.; Ka-tori, R.; Ishikawa, K.; Hirota, Y. Clin. Cardiol. 1991, 14, 53. doi: 10.1002/clc.4960140112
10. [10]
  Dreyfuss, J.; Cohen, A. I.; Hess, S. M. J. Pharm. Sci. 1968, 57, 1505. doi: 10.1002/jps.2600570907
11. [11]
  Feng, Z. Y.; Wang, Z. G. J. Psychiatry 2010, 23, 475(in Chinese). doi: 10.3969/j.issn.1009-7201.2010.06.031
12. [12]
  Farzana, L. A.; Fatima, I.; Ihsan-ul-Haq.; Bushra, M.; Mohammad, B.; Umer, R. Bioorg. Med. Chem. 2008, 16, 7691 doi: 10.1016/j.bmc.2008.07.009
13. [13]
  Roberto, D. S.; Roberta, C. Farmaco 2005, 60, 385. doi: 10.1016/j.farmac.2005.03.006
14. [14]
  Satyanarayana, K.; Rao, M. N. A. Indian J. Pharm. Sci. 1993, 55, 230.
15. [15]
  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. doi: 10.1016/j.bmcl.2003.08.051
16. [16]
  Arya, K.; Dandia, A. Bioorg. Med. Chem. Lett. 2008, 18, 114. doi: 10.1016/j.bmcl.2007.11.002
17. [17]
  Satbir, M.; Savita, N.; Suchita, S.; Mohini, K.; Gurdeep, S.; Vi-render, S. J. Heterocycl. Chem. 2017, 54, 3282. doi: 10.1002/jhet.2948
18. [18]
  Zhang, J.; Mu, B. S.; Wu, M.; Bian, Y. Q.; Li, Y. Chem. J. Chin. Univ. 2015, 36, 687(in Chinese).
19. [19]
  Kamal, A.; Shankaraiah, N.; Devaiah, V.; Reddy, K. L.; Juvekar, A.; Sen, S.; Kurian, N.; Zingde, S. Bioorg. Med. Chem. Lett. 2008, 18, 1468. doi: 10.1016/j.bmcl.2007.12.063
20. [20]
  Buckler, R. T.; Hartzler, H. E.; Kurchacova, E.; Nichols, G.; Phillips, B. M. J. Med. Chem. 1978, 21, 1254. doi: 10.1021/jm00210a015
21. [21]
  Kim, S.; Cho, S. N.; Oh, T.; Kim, P. Bioorg. Med. Chem. Lett. 2012, 22, 6844. doi: 10.1016/j.bmcl.2012.09.041
22. [22]
  Dorota, G. P.; Jan, B.; Iwona, E. G. Eur. J. Med. Chem. 2012, 47, 501. doi: 10.1016/j.ejmech.2011.11.021
23. [23]
  Aher, N. G.; Pore, V. S.; Mishra, N. N.; Kumar, A.; Shukla, P. K.; Sharma, A.; Bhat, M. K. Bioorg. Med. Chem. Lett. 2009, 19, 759. doi: 10.1016/j.bmcl.2008.12.026
24. [24]
  Guo, X. L.; Yu, Z.; Yan, X. F.; Gao, C. World Notes Antibiot. 2018, 39, 286(in Chinese). doi: 10.3969/j.issn.1001-8751.2018.04.004
25. [25]
  Wang, Y.; Kong, L. M.; Wang, R. R.; Tian, K. Q.; Zhang, P. Chin. J. Org. Chem. 2019, 39, 2663(in Chinese).
26. [26]
  Shunsaku, O.; Ikuo, K.; Takahiro, U.; Masayuki, Y.; Tomomichi, Y.; Satoshi, Y. Chem. Pharm. Bull. 1997, 45, 1140. doi: 10.1248/cpb.45.1140
27. [27]
  Joule J. A.; Mills K. Heterocyclic Chemistry, John Wiley & Sons Ltd, UK, 2010, p. 557.
28. [28]
  Kong, L. M. M.S. Thesis, Hebei Normal University, Shijiazhuang, 2017 (in Chinese).
29. [29]
  Wang, L. Z.; Zhang, P.; Zhang, X. M.; Zhang, Y. H.; Li, Y.; Wang, Y. X. Eur. J. Med. Chem. 2009, 44, 2815. doi: 10.1016/j.ejmech.2008.12.021
1. [1]
  Xuejie Wang , Guoqing Cui , Congkai Wang , Yang Yang , Guiyuan Jiang , Chunming Xu . 碳基催化剂催化有机液体氢载体脱氢研究进展. Acta Physico-Chimica Sinica, 2025, 41(5): 100044-. doi: 10.1016/j.actphy.2024.100044
2. [2]
  Tianlong Zhang , Rongling Zhang , Hongsheng Tang , Yan Li , Hua Li . Online Monitoring and Mechanistic Analysis of 3,5-diamino-1,2,4-triazole (DAT) Synthesis via Raman Spectroscopy: A Recommendation for a Comprehensive Instrumental Analysis Experiment. University Chemistry, 2024, 39(6): 303-311. doi: 10.3866/PKU.DXHX202312006
3. [3]
  Liyang ZHANG , Dongdong YANG , Ning LI , Yuanyu YANG , Qi MA . Crystal structures, luminescent properties and Hirshfeld surface analyses of three cadmium(Ⅱ) complexes based on 2-(3-(pyridin-2-yl)-1H-pyrazol-1-yl)benzoate. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1943-1952. doi: 10.11862/CJIC.20240079
4. [4]
  Xinting XIONG , Zhiqiang XIONG , Panlei XIAO , Xuliang NIE , Xiuying SONG , Xiuguang YI . Synthesis, crystal structures, Hirshfeld surface analysis, and antifungal activity of two complexes Na(Ⅰ)/Cd(Ⅱ) assembled by 5-bromo-2-hydroxybenzoic acid ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1661-1670. doi: 10.11862/CJIC.20240145
5. [5]
  Shuhui Li , Rongxiuyuan Huang , Yingming Pan . Electrochemical Synthesis of 2,5-Diphenyl-1,3,4-Oxadiazole: A Recommended Comprehensive Organic Chemistry Experiment. University Chemistry, 2025, 40(5): 357-365. doi: 10.12461/PKU.DXHX202407028
6. [6]
  Xiaoyang Li , Xiaowei Huang , Yimeng Zhang , Huan Liu , Shao Jin , Junpeng Zhuang . Comprehensive Chemical Experiments on the Synthesis of 1,3-Dibromo-5,5-Dimethylhydantoin and Its Application as a Brominating Reagent. University Chemistry, 2025, 40(7): 286-293. doi: 10.12461/PKU.DXHX202408035
7. [7]
  Aidang Lu , Yunting Liu , Yanjun Jiang . Comprehensive Organic Chemistry Experiment: Synthesis and Characterization of Triazolopyrimidine Compounds. University Chemistry, 2024, 39(8): 241-246. doi: 10.3866/PKU.DXHX202401029
8. [8]
  Yanglin Jiang , Mingqing Chen , Min Liang , Yige Yao , Yan Zhang , Peng Wang , Jianping Zhang . Experimental and Theoretical Investigations of Solvent Polarity Effect on ESIPT Mechanism in 4′-N,N-diethylamino-3-hydroxybenzoflavone. Acta Physico-Chimica Sinica, 2025, 41(2): 100012-. doi: 10.3866/PKU.WHXB202309027
9. [9]
  Jingzhao Cheng , Shiyu Gao , Bei Cheng , Kai Yang , Wang Wang , Shaowen Cao . 4-氨基-1H-咪唑-5-甲腈修饰供体-受体型氮化碳光催化剂的构建及其高效光催化产氢研究. Acta Physico-Chimica Sinica, 2024, 40(11): 2406026-. doi: 10.3866/PKU.WHXB202406026
10. [10]
  Hong RAO , Yang HU , Yicong MA , Chunxin LÜ , Wei ZHONG , Lihua DU . Synthesis and in vitro anticancer activity of phenanthroline-functionalized nitrogen heterocyclic carbene homo- and heterobimetallic silver/gold complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2429-2437. doi: 10.11862/CJIC.20240275
11. [11]
  Mingjie Lei , Wenting Hu , Kexin Lin , Xiujuan Sun , Haoshen Zhang , Ye Qian , Tongyue Kang , Xiulin Wu , Hailong Liao , Yuan Pan , Yuwei Zhang , Diye Wei , Ping Gao . Co/Mn/Mo掺杂加速NiSe₂重构以提高其电催化尿素氧化性能. Acta Physico-Chimica Sinica, 2025, 41(8): 100083-. doi: 10.1016/j.actphy.2025.100083
12. [12]
  You Zhou , Li-Sheng Wang , Shuang-Gui Lei , Bo-Cheng Tang , Zhi-Cheng Yu , Xing Li , Yan-Dong Wu , Kai-Lu Zheng , An-Xin Wu . I₂-DMSO mediated tetra-functionalization of enaminones for the construction of novel furo[2′,3′:4,5]pyrimido[1,2-b]indazole skeletons via in situ capture of ketenimine cations. Chinese Chemical Letters, 2025, 36(1): 109799-. doi: 10.1016/j.cclet.2024.109799
13. [13]
  Gangsheng Li , Xiang Yuan , Fu Liu , Zhihua Liu , Xujie Wang , Yuanyuan Liu , Yanmin Chen , Tingting Wang , Yanan Yang , Peicheng Zhang . Three-step synthesis of flavanostilbenes with a 2-cyclohepten-1-one core by Cu-mediated [5 + 2] cycloaddition/decarboxylation cascade. Chinese Chemical Letters, 2025, 36(2): 109880-. doi: 10.1016/j.cclet.2024.109880
14. [14]
  Peiyan Zhu , Yanyan Yang , Hui Li , Jinhua Wang , Shiqing Li . Rh(Ⅲ)‐Catalyzed sequential ring‐retentive/‐opening [4 + 2] annulations of 2H‐imidazoles towards full‐color emissive imidazo[5,1‐a]isoquinolinium salts and AIE‐active non‐symmetric 1,1′‐biisoquinolines. Chinese Chemical Letters, 2024, 35(10): 109533-. doi: 10.1016/j.cclet.2024.109533
15. [15]
  Junjun Huang , Ran Chen , Yajian Huang , Hang Zhang , Anran Zheng , Qing Xiao , Dan Wu , Ruxia Duan , Zhi Zhou , Fei He , Wei Yi . Discovery of an enantiopure N-[2-hydroxy-3-phenyl piperazine propyl]-aromatic carboxamide derivative as highly selective α_1D/1A-adrenoceptor antagonist and homology modelling. Chinese Chemical Letters, 2024, 35(11): 109594-. doi: 10.1016/j.cclet.2024.109594
16. [16]
  Bairu Meng , Zongji Zhuo , Han Yu , Sining Tao , Zixuan Chen , Erik De Clercq , Christophe Pannecouque , Dongwei Kang , Peng Zhan , Xinyong Liu . Design, synthesis, and biological evaluation of benzo[4,5]thieno[2,3-d]pyrimidine derivatives as novel HIV-1 NNRTIs. Chinese Chemical Letters, 2024, 35(6): 108827-. doi: 10.1016/j.cclet.2023.108827
17. [17]
  Xiaoling LUO , Pintian ZOU , Xiaoyan WANG , Zheng LIU , Xiangfei KONG , Qun TANG , Sheng WANG . Synthesis, crystal structures, and properties of lanthanide metal-organic frameworks based on 2, 5-dibromoterephthalic acid ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1143-1150. doi: 10.11862/CJIC.20230271
18. [18]
  Yuanyuan Zeng , Fang Liu , Jun Wang , Bianfei Shao , Tao He , Zhongzheng Xiang , Yan Wang , Shunyao Zhu , Tian Yang , Siting Yu , Changyang Gong , Lei Liu . Fisetin micelles precisely exhibit a radiosensitization effect by inhibiting PDGFRβ/STAT1/STAT3/Bcl-2 signaling pathway in tumor. Chinese Chemical Letters, 2025, 36(2): 109734-. doi: 10.1016/j.cclet.2024.109734
19. [19]
  Zhenghua ZHAO , Qin ZHANG , Yufeng LIU , Zifa SHI , Jinzhong GU . Syntheses, crystal structures, catalytic and anti-wear properties of nickel(Ⅱ) and zinc(Ⅱ) coordination polymers based on 5-(2-carboxyphenyl)nicotinic acid. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 621-628. doi: 10.11862/CJIC.20230342
20. [20]
  Qianqian Liu , Xing Du , Wanfei Li , Wei-Lin Dai , Bo Liu . Synergistic Effects of Internal Electric and Dipole Fields in SnNb₂O₆/Nitrogen-Enriched C₃N₅ S-Scheme Heterojunction for Boosting Photocatalytic Performance. Acta Physico-Chimica Sinica, 2024, 40(10): 2311016-. doi: 10.3866/PKU.WHXB202311016

Get Citation

PDF

XML

Metrics

PDF Downloads(17)
Abstract views(2890)
HTML views(382)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142