Synthesis Antimicrobial Activities and Side Reactions of 4-Methyl-3-acetyl-2-heterocyclic-2H,3H-benzo[f]-1,5-thiazepines

doi:10.6023/cjoc201212027

Chin. J. Org. Chem. ›› 2013, Vol. 33 ›› Issue (07): 1465-1471.DOI: 10.6023/cjoc201212027 Previous Articles Next Articles

Articles

4-甲基-3-乙酰基-2-杂环-2H,3H-苯并[f]-1,5-硫氮杂(卄卓)衍生物的合成、抑菌活性及副反应的研究

武云云^a, 田克情^c, 杨田^a, 杜星琼^b, 张萍^a

a 河北师范大学化学与材料科学学院石家庄 050024;
b 河北师范大学生命科学学院石家庄 050024;
c 河北化工医药职业技术学院化学与环境工程系石家庄 050026

收稿日期:2012-12-23 修回日期:2013-02-08 发布日期:2013-03-14
通讯作者: 张萍 E-mail:zhangpingp@sina.com
基金资助:
国家自然科学基金(No. 20972040)资助项目.

Synthesis Antimicrobial Activities and Side Reactions of 4-Methyl-3-acetyl-2-heterocyclic-2H,3H-benzo[f]-1,5-thiazepines

Wu Yunyun^a, Tian Keqing^c, Yang Tian^a, Du Xingqiong^b, Zhang Ping^a

a College of Chemistry, 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:2012-12-23 Revised:2013-02-08 Published:2013-03-14
Supported by:
Project supported by the National Natural Science Foundation of China (No. 20972040).

Starting from substituted heterocyclic aldehyde and acetylacetone, a series of new 4-methyl-3-acetyl-2-heterocyc-lic-2H,3H-benzo[f]-1,5-thiazepines 3a～3l were synthesized through 3-step reactions. The structures of the new products were confirmed by ¹H NMR, IR, MS and elemental analysis, and the imine-enamine tautomerism of the target compouds was investigated by means of ¹H NMR spectroscopy. Their antifungal activities were evaluated, and the results provides the inspiration for structure-activity reationship of the benzothiazepines. Meanwhile, the structure of the main by-products of 3h was identified, and the possible mechanism of the by-products was proposed.

Key words: 1,5-benzothiazepine, heterocyclic, side reaction, antifungal activity

Cite this article

Wu Yunyun, Tian Keqing, Yang Tian, Du Xingqiong, Zhang Ping. Synthesis Antimicrobial Activities and Side Reactions of 4-Methyl-3-acetyl-2-heterocyclic-2H,3H-benzo[f]-1,5-thiazepines[J]. Chin. J. Org. Chem., 2013, 33(07): 1465-1471.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Fabrizio, M.; Fabio, D.; Aldo, F.; Merlo, G. J. Comb. Chem. 2001, 3, 224.
[2] Prakash, O.; Kumar, A.; Sadana, A.; Prakash, R.; Singh, S. P.; Claramunt, R. M.; Sanz, D.; Alkorta, I.; Elguero, J. Tetrahedron 2005, 61, 6642.
[3] Nagao, T.; Sato, M.; Iwasawa, Y.; Takada, T.; Ishida, R. Jpn. J. Pharmacol. 1972, 22, 467.
[4] Nagao, T.; Sato, M.; Nakajima, H.; Kiyomoto, A. Chem. Pharm. Bull. 1973, 21, 92.
[5] Yamada, K.; Shimamura, T.; Nakajima, H. Jpn. J. Pharmacol. 1973, 23, 321.
[6] Bariwal, J. B.; Upadhyay, K. D.; Manvar, A. T.; Trivedi, J. C.; Singh, J. S.; Jain, K. S.; Shah, A. K. Eur. J. Med. Chem. 2008, 43, 2279.
[7] Grandolini, G.; Perioli, L.; Ambrogi, V. Eur. J. Med. Chem. 1999, 34, 701.
[8] Bajaj, K.; Archana; Kumar, A. Eur. J. Med. Chem. 2004, 39, 369.
[9] Ambrogi, V.; Furlani, A.; Grandolini, G.; Papaioannou, A.; Perioli, L.; Scarcia, V.; Tuttobello, L. Eur. J. Med. Chem. 1993, 28, 659.
[10] Maruenda, H.; Johnson, F. J. Med. Chem. 1995, 38, 2145.
[11] Roberto. S.; Roberta. C. Farmaco 2005, 60, 385.
[12] Zhang, P.; Wang, L.-Z.; Wu, H.-S.; Lan, J.-M.; Li, Y.; Wang, Y.-X. Chin. Chem. Lett. 2009, 20, 660 (in Chinese). (张萍, 王兰芝, 吴惠姝, 蓝佳明, 李媛, 王永祥, 中国化学快报, 2009, 20, 660.)
[13] 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.)
[14] 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.)
[15] Zhang, P.; Huang, J. H.; Wang, L.-Z.; Liu, W.; Li, Y. Chin. J. Org. Chem. 2010, 30, 1939 (in Chinese). (张萍, 黄金华, 王兰芝, 刘薇, 李媛, 有机化学, 2010, 30, 1939.)
[16] Li, W.-H.; Zhang, L. F.; Liu, W.; Du, X. Q.; Li, Y. Chin. J. Org. Chem. 2011, 31, 1252 (in Chinese). (李文红, 张玲芬, 刘薇, 杜星琼, 李媛, 有机化学, 2011, 31, 1252.)
[17] Wang, L.-Z.; Zhang, P.; Zhang, X.-M.; Zhang, Y.-H.; Wang, Y.-X.; Li, Y. Eur. J. Med. Chem. 2009, 44, 2815.
[18] Qiu, S. L.; Wang, L.-Z.; Li, W.-H.; Li, Y. Acta Chim. Sinica 2011, 69, 1217 (in Chinese). (邱召来, 王兰芝, 李文红, 李媛, 化学学报, 2011, 69, 1217.)
[19] Hooton, T. M. Infect. Dis. Clin. North. Am. 2003, 17, 303.
[20] Gallo-Martínez, L.; Campín-Falcó, P.; Sevillano-Cabeza, A. J. Pharm. Biomed. Anal. 2002, 29, 405.
[21] Liu, M.; Zhang, W.-J.; Gao, N. Chem. Reag. 2009, 31, 795 (in Chinese). (刘敏, 章文军, 高宁, 化学试剂, 2009, 31, 795.)
[22] Xing, Y.; Xie, Z.-F.; Liu, F.-M. Chem. J. Chin. Univ. 2008, 29, 533 (in Chinese). (邢烨, 解正峰, 刘方明, 高等学校化学学报, 2008, 29, 533.)
[23] Yang, D. B.; Liu, F. M.; Shen, S. W.; Chen, S. Q. Chin. J. Org. Chem. 2010, 30, 244 (in Chinese). (杨德保, 刘方明, 沈松伟, 陈盛钦, 有机化学, 2010, 30, 244.)
[24] Nishiyama, Y.; Makino, Y.; Hamanaka, S.; Ogawa, A.; Sonoda, N. Bull. Chem. Soc. Jpn. 1989, 62, 1683.

4-甲基-3-乙酰基-2-杂环-2H,3H-苯并[f]-1,5-硫氮杂(卄卓)衍生物的合成、抑菌活性及副反应的研究

Synthesis Antimicrobial Activities and Side Reactions of 4-Methyl-3-acetyl-2-heterocyclic-2H,3H-benzo[f]-1,5-thiazepines

PDF

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Dengpeng Xia, Jinyun Luo, Lin He, Zhihua Cai, Guangfen Du. N-Heterocyclic Carbene-Catalyzed Synthesis of Pentafluorophenyl Sulfides [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 622-630.
[2]	Shuang Yang, Xinqiang Fang. Kinetic Resolutions Enabled by N-Heterocyclic Carbene Catalysis: An Update [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 448-480.
[3]	Yuanlin Cai, Ya Lü, Guihua Nie, Zhichao Jin, Yonggui Chi. Recent Advances in the Synthesis of Cyanides Enabled by N-Heterocyclic Carbene Catalysis [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3135-3145.
[4]	Feng Wang, Yu Chen, Hongyan Pei, Jing Zhang, Lixin Zhang. Design, Synthesis and Antifungal Activities of Novel 1,2,4-Oxadiazole Derivatives Containing Piperidine [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2826-2836.
[5]	Yuzhuo Chen, Hongmei Sun, Liang Wang, Fangzhi Hu, Shuaishuai Li. Research Progress on Construction of Heterocyclic Skeletons Based on α-Hydride Transfer Strategy [J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2323-2337.
[6]	Liangru Yang, Mengli Guo, Jinwei Yuan, Jiamei Wangx, Yuting Xia, Yongmei Xiao, Pu Mao. Research Progress on Pincer N-Heterocyclic Carbene Metal Complexes [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2002-2025.
[7]	Xinyu Zhang, Huihui Geng, Shilei Zhang, Wei Wang, Xiaobei Chen. A Method for the Synthesis of Deuterated Benzoins Catalyzed by N-Heterocyclic Carbene [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1510-1516.
[8]	Kanghui Duan, Junlong Tang, Wanqing Wu. Recent Advances in the Synthesis of Fused Heterocyclic Compounds and Their Antitumor Activities [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 826-854.
[9]	Chunbo Dai, Siqi Xia, Xiaoyu Chen, Limin Yang. N-Heterocyclic Carbene (NHC)-Catalyzed [4+3] Cycloaddition to Synthesize 4-Aminobenzoheptenolactons [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 1084-1090.
[10]	Meng Li, Dongguo Xia, Yunxiao Wang, Xiang Cheng, Jiexiu Gong, Yao Chen, Xianhai Lü. Design, Synthesis and Antifungal Bioactivity Evaluation of Thiazole Benzoate Derivatives [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 686-696.
[11]	Tingting Liu, Yucai Hu, An Shen. Mechanism of Carbon-Carbon Coupling Reactions Catalyzed by Imine-Ligand-Assisted N-Heterocyclic Carbene Palladium Complexes [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 622-628.
[12]	Guijie Liu, Zhengqiang Fu, Fei Chen, Caixia Xu, Min Li, Ning Liu. N-Heterocyclic Carbene-Pyridine Manganese Complex/ Tetrabutylammonium Iodide Catalyzed Synthesis of Cyclic Carbonate from CO₂ and Epoxide [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 629-635.
[13]	Erjun Hao, Xiaobo Ding, Kexin Wang, Honghao Zhou, Qiliang Yang, Lei Shi. Recent Progress on [3+2] Ring-Expansion Reaction of Aziridines with Unsaturated Compounds [J]. Chinese Journal of Organic Chemistry, 2023, 43(12): 4057-4074.
[14]	Yushan Zhang, Zhen Huan, Jindong Yang, Jinpei Cheng. Recent Advances in Hydrogen Transfer Reactivities of N-Heterocyclic Phosphines [J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3806-3825.
[15]	Qiushan Gao, Meng Li, Wanqing Wu. Recent Advances in Transition Metal-Catalyzed Isocyanide Insertion Reactions [J]. Chinese Journal of Organic Chemistry, 2022, 42(9): 2659-2681.