Synthesis and Antimicrobial Activity of 1,5-Benzothiazepines Incorporated with Triazole Moiety

doi:10.6023/cjoc202012044

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (6): 2361-2373.DOI: 10.6023/cjoc202012044 Previous Articles Next Articles

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含三氮唑结构的1,5-苯并硫氮杂䓬的合成及抑菌活性

孙雨佳^a, 王紫薇^a, 王岩^a, 许同绣^a, 田克情^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:2020-12-27 修回日期:2021-02-09 发布日期:2021-03-12
通讯作者: 张萍
基金资助:
河北省自然科学基金(B2017205100); 河北师范大学研究生创新基金(CXZZSS2021052)

Synthesis and Antimicrobial Activity of 1,5-Benzothiazepines Incorporated with Triazole Moiety

Yujia Sun^a, Ziwei Wang^a, Yan Wang^a, Tongxiu Xu^a, Keqing Tian^b, Ping Zhang^a()

a College of Chemistry and Materials Science, Hebei Normal University, Shijiazhuang 050024
b Department of Environment and Chemical Engineering, Hebei Chemical and Pharmaceutical College, Shijiazhuang 050026

Received:2020-12-27 Revised:2021-02-09 Published:2021-03-12
Contact: Ping Zhang
Supported by:
Natural Science Foundation of Hebei Province(B2017205100); Graduate Student Innovation Fundation of Hebei Normal University(CXZZSS2021052)

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Abstract

Four kinds of 1,5-benzothiazepines incorporated with triazole moiety: 2,3/2,5-dihydro-3-[(1H-1,2,4-triazol-1-yl) methyl]-4-aryl-1,5-benzothiazepines (9a~9f,10a~10f) and 2,3/2,5-dihydro-3-[(2H-1,2,3-triazol-2-yl)methyl]-4-aryl-1,5- benzothiazepines (17a~17f, 18a~18f) were designed and synthesized. It was found that the isomerization of triazole occurred during the conversion of 15a~15f to the target compounds. Two new compounds 19a and 20a were isolated and their possible formation mechanism was proposed. The antimicrobial activity test of the target products showed that compounds 9a~9d and 10a~10d had moderate to high inhibitory effect on fungi, and compounds 9b, 9c, and 10b showed higher inhibition on C. neoformans than that of fluconazole, which can be used for further investigation for the development of antifungal drugs.

Key words: triazole, 1, 5-benzothiazepine, antimicrobial activity

Cite this article

Yujia Sun, Ziwei Wang, Yan Wang, Tongxiu Xu, Keqing Tian, Ping Zhang. Synthesis and Antimicrobial Activity of 1,5-Benzothiazepines Incorporated with Triazole Moiety[J]. Chinese Journal of Organic Chemistry, 2021, 41(6): 2361-2373.

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Compd.	R	C. neoformans stand	C. neoformans clinical	C. albicans	S. aureus	E. coli
9a	H	16.6	15.9	16.2	7.8	8.4
9b	F	24.7	27.6	14.9	6.8	8.0
9c	Cl	23.4	12.7	12.9	7.8	8.8
9d	Br	21.2	12.0	12.2	7.6	8.1
9e	CH₃	6.0	6.0	10.4	6.0	6.0
9f	OCH₃	6.0	6.0	6.0	6.0	6.0
10a	H	13.0	11.5	16.2	6.0	6.0
10b	F	29.4	30.0	14.3	6.0	6.0
10c	Cl	15.3	16.5	14.2	6.0	6.0
10d	Br	11.3	6.0	6.0	6.0	6.0
10e	CH₃	6.0	6.0	6.0	6.0	6.0
10f	OCH₃	6.0	6.0	6.0	6.0	6.0
17a	H	6.0	6.0	6.0	6.0	6.0
17b	F	6.0	6.0	6.0	6.0	6.0
17c	Cl	6.0	6.0	6.0	6.0	6.0
17d	Br	6.0	6.0	6.0	6.0	6.0
17e	CH₃	6.0	6.0	6.0	6.0	6.0
17f	OCH₃	6.0	6.0	6.0	6.0	6.0
18a 18b 18c 18d 18e 18f 19a 20a Fluconazol	H F Cl Br CH₃ OCH₃ H H —	6.0 6.0 6.0 6.0 6.0 6.0 6.0 6.0 22.4	6.0 6.0 6.0 6.0 6.0 6.0 6.0 6.0 22.4	6.0 6.0 6.0 6.0 6.0 6.0 6.0 6.0 20.2	6.0 6.0 6.0 6.0 6.0 6.0 6.0 6.0 —	6.0 6.0 6.0 6.0 6.0 6.0 6.0 6.0 —
Ciprofloxacin hydrochloride	—	—	—	—	21.6	21.6

Compd.	R	C. neoformans stand	C. neoformans clinical	C. albicans	S. aureus	E. coli
9a	H	16.6	15.9	16.2	7.8	8.4
9b	F	24.7	27.6	14.9	6.8	8.0
9c	Cl	23.4	12.7	12.9	7.8	8.8
9d	Br	21.2	12.0	12.2	7.6	8.1
9e	CH₃	6.0	6.0	10.4	6.0	6.0
9f	OCH₃	6.0	6.0	6.0	6.0	6.0
10a	H	13.0	11.5	16.2	6.0	6.0
10b	F	29.4	30.0	14.3	6.0	6.0
10c	Cl	15.3	16.5	14.2	6.0	6.0
10d	Br	11.3	6.0	6.0	6.0	6.0
10e	CH₃	6.0	6.0	6.0	6.0	6.0
10f	OCH₃	6.0	6.0	6.0	6.0	6.0
17a	H	6.0	6.0	6.0	6.0	6.0
17b	F	6.0	6.0	6.0	6.0	6.0
17c	Cl	6.0	6.0	6.0	6.0	6.0
17d	Br	6.0	6.0	6.0	6.0	6.0
17e	CH₃	6.0	6.0	6.0	6.0	6.0
17f	OCH₃	6.0	6.0	6.0	6.0	6.0
18a 18b 18c 18d 18e 18f 19a 20a Fluconazol	H F Cl Br CH₃ OCH₃ H H —	6.0 6.0 6.0 6.0 6.0 6.0 6.0 6.0 22.4	6.0 6.0 6.0 6.0 6.0 6.0 6.0 6.0 22.4	6.0 6.0 6.0 6.0 6.0 6.0 6.0 6.0 20.2	6.0 6.0 6.0 6.0 6.0 6.0 6.0 6.0 —	6.0 6.0 6.0 6.0 6.0 6.0 6.0 6.0 —
Ciprofloxacin hydrochloride	—	—	—	—	21.6	21.6

Compd.	R	MIC₈₀		MFC
Compd.	R	ATCC34874	Clinical isolate	ATCC34874	Clinical isolate
9a	H	4.6	4.6	90.0	90.0
9b	F	2.2	2.2	61.0	62.0
9c	Cl	3.0	5.0	79.0	95.0
9d 10b	Br F	3.5 2.0	5.0 2.0	73.0 63.0	89.0 63.0
Fluconazol	—	2.0	3.0	>128.0	>128.0

Compd.	R	MIC₈₀		MFC
Compd.	R	ATCC34874	Clinical isolate	ATCC34874	Clinical isolate
9a	H	4.6	4.6	90.0	90.0
9b	F	2.2	2.2	61.0	62.0
9c	Cl	3.0	5.0	79.0	95.0
9d 10b	Br F	3.5 2.0	5.0 2.0	73.0 63.0	89.0 63.0
Fluconazol	—	2.0	3.0	>128.0	>128.0

含三氮唑结构的1,5-苯并硫氮杂䓬的合成及抑菌活性

Synthesis and Antimicrobial Activity of 1,5-Benzothiazepines Incorporated with Triazole Moiety

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