Synthesis and Antimicrobial Activity of 1,2-Benzothiazine Derivatives

Patel, Chandani; Bassin, Jatinder; Scott, Mark; Flye, Jenna; Hunter, Ann; Martin, Lee; Goyal, Madhu

doi:10.3390/molecules21070861

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Synthesis and Antimicrobial Activity of 1,2-Benzothiazine Derivatives

Chandani Patel, Jatinder Bassin, Mark Scott, Jenna Flye, Ann Hunter, Lee Martin

, Madhu Goyal

Molecules, Volume: 21, Issue: 7, Start page: 861

Swansea University Authors: Jenna Flye, Ann Hunter

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DOI (Published version): 10.3390/molecules21070861

Abstract

A number of 1,2-benzothiazines have been synthesized in a three-step process. Nine chalcones 1–9 bearing methyl, fluoro, chloro and bromo substituents were chlorosulfonated with chlorosulfonic acid to generate the chalcone sulfonyl chlorides 10–18. These were converted to the dibromo compounds 19–27...

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Published in:	Molecules
ISSN:	1420-3049
Published:	MDPI AG 2016
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These were converted to the dibromo compounds 19–27 through reaction with bromine in glacial acetic acid. Compounds 19–27 were reacted with ammonia, methylamine, ethylamine, aniline and benzylamine to generate a library of 45 1,2-benzothiazines 28–72. Compounds 28–72 were evaluated for their antimicrobial activity using broth microdilution techniques against two Gram-positive bacteria (Bacillus subtilis and Staphylococcus aureus) and two Gram-negative bacteria (Proteus vulgaris and Salmonella typhimurium). The results demonstrated that none of the compounds showed any activity against Gram-negative bacteria P. vulgaris and S. typhimurium; however, compounds 31, 33, 38, 43, 45, 50, 53, 55, 58, 60, 63 and 68 showed activity against Gram-positive bacteria Bacillus subtilis and Staphylococcous aureus. The range of minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) was 25–600 µg/mL, though some of the MIC and MBC concentrations were high, indicating weak activity. Structure activity relationship studies revealed that the compounds with a hydrogen atom or an ethyl group on the nitrogen of the thiazine ring exerted antibacterial activity against Gram-positive bacteria. The results also showed that the compounds where the benzene ring of the benzoyl moiety contained a methyl group or a chlorine or bromine atom in the para position showed higher antimicrobial activity. 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spelling	2022-11-29T11:44:06.6669972 v2 61776 2022-11-04 Synthesis and Antimicrobial Activity of 1,2-Benzothiazine Derivatives 6068cc06fdaeed79c269ca4eaf9c8e25 Jenna Flye Jenna Flye true false 5c583a55906567a426ad699a8d0d6607 Ann Hunter Ann Hunter true false 2022-11-04 PMSC A number of 1,2-benzothiazines have been synthesized in a three-step process. Nine chalcones 1–9 bearing methyl, fluoro, chloro and bromo substituents were chlorosulfonated with chlorosulfonic acid to generate the chalcone sulfonyl chlorides 10–18. These were converted to the dibromo compounds 19–27 through reaction with bromine in glacial acetic acid. Compounds 19–27 were reacted with ammonia, methylamine, ethylamine, aniline and benzylamine to generate a library of 45 1,2-benzothiazines 28–72. Compounds 28–72 were evaluated for their antimicrobial activity using broth microdilution techniques against two Gram-positive bacteria (Bacillus subtilis and Staphylococcus aureus) and two Gram-negative bacteria (Proteus vulgaris and Salmonella typhimurium). The results demonstrated that none of the compounds showed any activity against Gram-negative bacteria P. vulgaris and S. typhimurium; however, compounds 31, 33, 38, 43, 45, 50, 53, 55, 58, 60, 63 and 68 showed activity against Gram-positive bacteria Bacillus subtilis and Staphylococcous aureus. The range of minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) was 25–600 µg/mL, though some of the MIC and MBC concentrations were high, indicating weak activity. Structure activity relationship studies revealed that the compounds with a hydrogen atom or an ethyl group on the nitrogen of the thiazine ring exerted antibacterial activity against Gram-positive bacteria. The results also showed that the compounds where the benzene ring of the benzoyl moiety contained a methyl group or a chlorine or bromine atom in the para position showed higher antimicrobial activity. Similar influences were identified where either a bromine or chlorine atom was in the meta position. Journal Article Molecules 21 7 861 MDPI AG 1420-3049 1,2-benzothiazines; chalcones; Bacillus subtilis; Staphylococcous aureus; Proteus vulgaris; Salmonella typhimurium 30 6 2016 2016-06-30 10.3390/molecules21070861 COLLEGE NANME Medicine COLLEGE CODE PMSC Swansea University The authors are grateful to the University of Hertfordshire for providing funds for Open Access 2022-11-29T11:44:06.6669972 2022-11-04T08:24:00.3415560 Faculty of Medicine, Health and Life Sciences Swansea University Medical School - Medicine Chandani Patel 1 Jatinder Bassin 2 Mark Scott 3 Jenna Flye 4 Ann Hunter 5 Lee Martin 0000-0002-5330-5700 6 Madhu Goyal 7 61776__25949__83d8d94abd184f63ad69623fc6379dec.pdf 61776.pdf 2022-11-29T11:42:37.9003672 Output 910949 application/pdf Version of Record true © 2016 by the authors; licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC-BY) license true eng http://creativecommons.org/licenses/by/4.0/
title	Synthesis and Antimicrobial Activity of 1,2-Benzothiazine Derivatives
spellingShingle	Synthesis and Antimicrobial Activity of 1,2-Benzothiazine Derivatives Jenna Flye Ann Hunter
title_short	Synthesis and Antimicrobial Activity of 1,2-Benzothiazine Derivatives
title_full	Synthesis and Antimicrobial Activity of 1,2-Benzothiazine Derivatives
title_fullStr	Synthesis and Antimicrobial Activity of 1,2-Benzothiazine Derivatives
title_full_unstemmed	Synthesis and Antimicrobial Activity of 1,2-Benzothiazine Derivatives
title_sort	Synthesis and Antimicrobial Activity of 1,2-Benzothiazine Derivatives
author_id_str_mv	6068cc06fdaeed79c269ca4eaf9c8e25 5c583a55906567a426ad699a8d0d6607
author_id_fullname_str_mv	6068cc06fdaeed79c269ca4eaf9c8e25_*_Jenna Flye 5c583a55906567a426ad699a8d0d6607_*_Ann Hunter
author	Jenna Flye Ann Hunter
author2	Chandani Patel Jatinder Bassin Mark Scott Jenna Flye Ann Hunter Lee Martin Madhu Goyal
format	Journal article
container_title	Molecules
container_volume	21
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container_start_page	861
publishDate	2016
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doi_str_mv	10.3390/molecules21070861
publisher	MDPI AG
college_str	Faculty of Medicine, Health and Life Sciences
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department_str	Swansea University Medical School - Medicine{{{_:::_}}}Faculty of Medicine, Health and Life Sciences{{{_:::_}}}Swansea University Medical School - Medicine
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description	A number of 1,2-benzothiazines have been synthesized in a three-step process. Nine chalcones 1–9 bearing methyl, fluoro, chloro and bromo substituents were chlorosulfonated with chlorosulfonic acid to generate the chalcone sulfonyl chlorides 10–18. These were converted to the dibromo compounds 19–27 through reaction with bromine in glacial acetic acid. Compounds 19–27 were reacted with ammonia, methylamine, ethylamine, aniline and benzylamine to generate a library of 45 1,2-benzothiazines 28–72. Compounds 28–72 were evaluated for their antimicrobial activity using broth microdilution techniques against two Gram-positive bacteria (Bacillus subtilis and Staphylococcus aureus) and two Gram-negative bacteria (Proteus vulgaris and Salmonella typhimurium). The results demonstrated that none of the compounds showed any activity against Gram-negative bacteria P. vulgaris and S. typhimurium; however, compounds 31, 33, 38, 43, 45, 50, 53, 55, 58, 60, 63 and 68 showed activity against Gram-positive bacteria Bacillus subtilis and Staphylococcous aureus. The range of minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) was 25–600 µg/mL, though some of the MIC and MBC concentrations were high, indicating weak activity. Structure activity relationship studies revealed that the compounds with a hydrogen atom or an ethyl group on the nitrogen of the thiazine ring exerted antibacterial activity against Gram-positive bacteria. The results also showed that the compounds where the benzene ring of the benzoyl moiety contained a methyl group or a chlorine or bromine atom in the para position showed higher antimicrobial activity. Similar influences were identified where either a bromine or chlorine atom was in the meta position.
published_date	2016-06-30T04:20:51Z
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Synthesis and Antimicrobial Activity of 1,2-Benzothiazine Derivatives

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