Synthesis, characterization and antimicrobial activity of new chalcones and their 6-aryl-4-(2,5-dichlorothiophen-3-yl)-6H-1,3-thiazin-2-amine derivatives

Chalcones (5a-h) were prepared in high yields via the condensation of 3-acetyl-2,5-dichlorothiophene (3) with aryl aldehydes (4a-h). The reaction of the resulting chalcones with thiourea in the presence of a catalytic amount of hydrochloric acid provided the 1,3-thiazin-2-amine derivatives (6a-g) in...

Full description

Saved in:
Bibliographic Details
Published in:Phosphorus, sulfur, and silicon and the related elements sulfur, and silicon and the related elements, 2017-01, Vol.192 (5), p.560-564
Main Authors: Al-Refai, Mahmoud, Ibrahim, Mohammad M., Alsohaili, Sohail, Geyer, Armin
Format: Article
Language:English
Subjects:
Antimicrobial agents
chalcone
Condensation
thiazine
thiophene
thiourea
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
cited_by
cites
container_end_page 564
container_issue 5
container_start_page 560
container_title Phosphorus, sulfur, and silicon and the related elements
container_volume 192
creator Al-Refai, Mahmoud
Ibrahim, Mohammad M.
Alsohaili, Sohail
Geyer, Armin
description Chalcones (5a-h) were prepared in high yields via the condensation of 3-acetyl-2,5-dichlorothiophene (3) with aryl aldehydes (4a-h). The reaction of the resulting chalcones with thiourea in the presence of a catalytic amount of hydrochloric acid provided the 1,3-thiazin-2-amine derivatives (6a-g) in moderate yields. All new compounds were characterized by extensive NMR analysis data, including 1D NMR experiments ( 1 H and 13 C) and 2D NMR experiments (COSY, HMBC, HSQC), as well as ESIMS and HRESIMS data. The newly synthesized compounds were evaluated for their biological activities, which demonstrate a very good to low bioactivities as antibacterial and antifungal, respectively.
doi_str_mv 10.1080/10426507.2016.1277526
format article
fullrecord <record><control><sourceid>proquest_infor</sourceid><recordid>TN_cdi_proquest_journals_1891110900</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>4321939539</sourcerecordid><originalsourceid>FETCH-LOGICAL-i240t-68e8f9804811e9fd2d96247f8d0864395b5ecb2c72739d4c520c84e1c50d5afa3</originalsourceid><addsrcrecordid>eNo1kc9KAzEQxhdRUKuPICx4UWjqJNlkszel-A8ED-p5SZMsG9kmmqQt65v4tqZaD8MMM7-Zj-ErijMMMwwCrjBUhDOoZwQwn2FS14zwveIIM04Ro4Tt5zozaAsdFscxvgNAQygcFd8vo0u9iTZOS9XLIFUywX7JZL0rpdM5kl1aFfzCyqHMY7u2aSx9Vzqz2a4MyjsTf9l8yIaSIxnGAVXogkwZ0lb1gw8-9dZ_9MYhisbhEvEHhKcU5a78sg4RJJfWmVJn8XUWX5t4Uhx0cojmdJcnxdvd7ev8AT093z_Ob56QJRUkxIURXSOgEhibptNEN5xUdSc0CF7Rhi2YUQuialLTRleKEVCiMlgx0Ex2kk6K87-7H8F_rkxM7btfBZclWywajDE0AJm6_qOs63xYyo0Pg26THPNvXZBO2dhSDO3WkPbfkHZrSLszhP4AIFh-wg</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1891110900</pqid></control><display><type>article</type><title>Synthesis, characterization and antimicrobial activity of new chalcones and their 6-aryl-4-(2,5-dichlorothiophen-3-yl)-6H-1,3-thiazin-2-amine derivatives</title><source>Taylor and Francis Science and Technology Collection</source><creator>Al-Refai, Mahmoud ; Ibrahim, Mohammad M. ; Alsohaili, Sohail ; Geyer, Armin</creator><creatorcontrib>Al-Refai, Mahmoud ; Ibrahim, Mohammad M. ; Alsohaili, Sohail ; Geyer, Armin</creatorcontrib><description>Chalcones (5a-h) were prepared in high yields via the condensation of 3-acetyl-2,5-dichlorothiophene (3) with aryl aldehydes (4a-h). The reaction of the resulting chalcones with thiourea in the presence of a catalytic amount of hydrochloric acid provided the 1,3-thiazin-2-amine derivatives (6a-g) in moderate yields. All new compounds were characterized by extensive NMR analysis data, including 1D NMR experiments ( 1 H and 13 C) and 2D NMR experiments (COSY, HMBC, HSQC), as well as ESIMS and HRESIMS data. The newly synthesized compounds were evaluated for their biological activities, which demonstrate a very good to low bioactivities as antibacterial and antifungal, respectively.</description><identifier>ISSN: 1042-6507</identifier><identifier>EISSN: 1563-5325</identifier><identifier>DOI: 10.1080/10426507.2016.1277526</identifier><language>eng</language><publisher>Abingdon: Taylor &amp; Francis</publisher><subject>Antimicrobial agents ; chalcone ; Condensation ; thiazine ; thiophene ; thiourea</subject><ispartof>Phosphorus, sulfur, and silicon and the related elements, 2017-01, Vol.192 (5), p.560-564</ispartof><rights>2017 Taylor &amp; Francis Group, LLC 2017</rights><rights>2017 Taylor &amp; Francis Group, LLC</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids></links><search><creatorcontrib>Al-Refai, Mahmoud</creatorcontrib><creatorcontrib>Ibrahim, Mohammad M.</creatorcontrib><creatorcontrib>Alsohaili, Sohail</creatorcontrib><creatorcontrib>Geyer, Armin</creatorcontrib><title>Synthesis, characterization and antimicrobial activity of new chalcones and their 6-aryl-4-(2,5-dichlorothiophen-3-yl)-6H-1,3-thiazin-2-amine derivatives</title><title>Phosphorus, sulfur, and silicon and the related elements</title><description>Chalcones (5a-h) were prepared in high yields via the condensation of 3-acetyl-2,5-dichlorothiophene (3) with aryl aldehydes (4a-h). The reaction of the resulting chalcones with thiourea in the presence of a catalytic amount of hydrochloric acid provided the 1,3-thiazin-2-amine derivatives (6a-g) in moderate yields. All new compounds were characterized by extensive NMR analysis data, including 1D NMR experiments ( 1 H and 13 C) and 2D NMR experiments (COSY, HMBC, HSQC), as well as ESIMS and HRESIMS data. The newly synthesized compounds were evaluated for their biological activities, which demonstrate a very good to low bioactivities as antibacterial and antifungal, respectively.</description><subject>Antimicrobial agents</subject><subject>chalcone</subject><subject>Condensation</subject><subject>thiazine</subject><subject>thiophene</subject><subject>thiourea</subject><issn>1042-6507</issn><issn>1563-5325</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><sourceid/><recordid>eNo1kc9KAzEQxhdRUKuPICx4UWjqJNlkszel-A8ED-p5SZMsG9kmmqQt65v4tqZaD8MMM7-Zj-ErijMMMwwCrjBUhDOoZwQwn2FS14zwveIIM04Ro4Tt5zozaAsdFscxvgNAQygcFd8vo0u9iTZOS9XLIFUywX7JZL0rpdM5kl1aFfzCyqHMY7u2aSx9Vzqz2a4MyjsTf9l8yIaSIxnGAVXogkwZ0lb1gw8-9dZ_9MYhisbhEvEHhKcU5a78sg4RJJfWmVJn8XUWX5t4Uhx0cojmdJcnxdvd7ev8AT093z_Ob56QJRUkxIURXSOgEhibptNEN5xUdSc0CF7Rhi2YUQuialLTRleKEVCiMlgx0Ex2kk6K87-7H8F_rkxM7btfBZclWywajDE0AJm6_qOs63xYyo0Pg26THPNvXZBO2dhSDO3WkPbfkHZrSLszhP4AIFh-wg</recordid><startdate>20170101</startdate><enddate>20170101</enddate><creator>Al-Refai, Mahmoud</creator><creator>Ibrahim, Mohammad M.</creator><creator>Alsohaili, Sohail</creator><creator>Geyer, Armin</creator><general>Taylor &amp; Francis</general><general>Taylor &amp; Francis Ltd</general><scope/></search><sort><creationdate>20170101</creationdate><title>Synthesis, characterization and antimicrobial activity of new chalcones and their 6-aryl-4-(2,5-dichlorothiophen-3-yl)-6H-1,3-thiazin-2-amine derivatives</title><author>Al-Refai, Mahmoud ; Ibrahim, Mohammad M. ; Alsohaili, Sohail ; Geyer, Armin</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-i240t-68e8f9804811e9fd2d96247f8d0864395b5ecb2c72739d4c520c84e1c50d5afa3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>Antimicrobial agents</topic><topic>chalcone</topic><topic>Condensation</topic><topic>thiazine</topic><topic>thiophene</topic><topic>thiourea</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Al-Refai, Mahmoud</creatorcontrib><creatorcontrib>Ibrahim, Mohammad M.</creatorcontrib><creatorcontrib>Alsohaili, Sohail</creatorcontrib><creatorcontrib>Geyer, Armin</creatorcontrib><jtitle>Phosphorus, sulfur, and silicon and the related elements</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Al-Refai, Mahmoud</au><au>Ibrahim, Mohammad M.</au><au>Alsohaili, Sohail</au><au>Geyer, Armin</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis, characterization and antimicrobial activity of new chalcones and their 6-aryl-4-(2,5-dichlorothiophen-3-yl)-6H-1,3-thiazin-2-amine derivatives</atitle><jtitle>Phosphorus, sulfur, and silicon and the related elements</jtitle><date>2017-01-01</date><risdate>2017</risdate><volume>192</volume><issue>5</issue><spage>560</spage><epage>564</epage><pages>560-564</pages><issn>1042-6507</issn><eissn>1563-5325</eissn><abstract>Chalcones (5a-h) were prepared in high yields via the condensation of 3-acetyl-2,5-dichlorothiophene (3) with aryl aldehydes (4a-h). The reaction of the resulting chalcones with thiourea in the presence of a catalytic amount of hydrochloric acid provided the 1,3-thiazin-2-amine derivatives (6a-g) in moderate yields. All new compounds were characterized by extensive NMR analysis data, including 1D NMR experiments ( 1 H and 13 C) and 2D NMR experiments (COSY, HMBC, HSQC), as well as ESIMS and HRESIMS data. The newly synthesized compounds were evaluated for their biological activities, which demonstrate a very good to low bioactivities as antibacterial and antifungal, respectively.</abstract><cop>Abingdon</cop><pub>Taylor &amp; Francis</pub><doi>10.1080/10426507.2016.1277526</doi><tpages>5</tpages></addata></record>
fulltext fulltext
identifier ISSN: 1042-6507
ispartof Phosphorus, sulfur, and silicon and the related elements, 2017-01, Vol.192 (5), p.560-564
issn 1042-6507
1563-5325
language eng
recordid cdi_proquest_journals_1891110900
source Taylor and Francis Science and Technology Collection
subjects Antimicrobial agents
chalcone
Condensation
thiazine
thiophene
thiourea
title Synthesis, characterization and antimicrobial activity of new chalcones and their 6-aryl-4-(2,5-dichlorothiophen-3-yl)-6H-1,3-thiazin-2-amine derivatives
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-02T15%3A06%3A18IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_infor&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Synthesis,%20characterization%20and%20antimicrobial%20activity%20of%20new%20chalcones%20and%20their%206-aryl-4-(2,5-dichlorothiophen-3-yl)-6H-1,3-thiazin-2-amine%20derivatives&rft.jtitle=Phosphorus,%20sulfur,%20and%20silicon%20and%20the%20related%20elements&rft.au=Al-Refai,%20Mahmoud&rft.date=2017-01-01&rft.volume=192&rft.issue=5&rft.spage=560&rft.epage=564&rft.pages=560-564&rft.issn=1042-6507&rft.eissn=1563-5325&rft_id=info:doi/10.1080/10426507.2016.1277526&rft_dat=%3Cproquest_infor%3E4321939539%3C/proquest_infor%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-i240t-68e8f9804811e9fd2d96247f8d0864395b5ecb2c72739d4c520c84e1c50d5afa3%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=1891110900&rft_id=info:pmid/&rfr_iscdi=true