Synthesis, Configuration, and Antimicrobial Properties of Novel Substituted and Cyclized '2′,3″-Thiazachalcones'

Nine new thiazachalcone‐based drugs, compounds 1–9, were prepared and fully characterized. The configurations of the photochemical‐dimerization products 7–9 were rationalized by semi‐empirical calculations. Both the experimental data and the theoretical calculations showed that the δ‐truxinic acid t...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Helvetica chimica acta 2007-08, Vol.90 (8), p.1482-1490
Hauptverfasser: Usta, Asu, Yaşar, Ahmet, Yılmaz, Nagihan, Güleç, Canan, Yaylı, Nuran, Karaoğlu, Şengül Alpay, Yaylı, Nurettin
Format: Artikel
Sprache:eng
Schlagworte:
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 1490
container_issue 8
container_start_page 1482
container_title Helvetica chimica acta
container_volume 90
creator Usta, Asu
Yaşar, Ahmet
Yılmaz, Nagihan
Güleç, Canan
Yaylı, Nuran
Karaoğlu, Şengül Alpay
Yaylı, Nurettin
description Nine new thiazachalcone‐based drugs, compounds 1–9, were prepared and fully characterized. The configurations of the photochemical‐dimerization products 7–9 were rationalized by semi‐empirical calculations. Both the experimental data and the theoretical calculations showed that the δ‐truxinic acid type dimer is the most stable isomer of all. All compounds were tested for their antibacterial and antifungal activities. The N‐alkylated congeners 4–6 showed strong antimicrobial activities against various bacteria and a yeast‐like fungus. The MIC and MBC values were as low as 0.1 μg/ml. All the compounds were active against the Gram‐positive bacterium Staphylococcus aureus.
doi_str_mv 10.1002/hlca.200790154
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_746295180</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>746295180</sourcerecordid><originalsourceid>FETCH-LOGICAL-c3594-b485a1cafff2e36b90bf3883ed1ea7ad3477ed7488433069a4c469d37d187c363</originalsourceid><addsrcrecordid>eNqFkMFuEzEQQC1EJULhynlvuWTDeO1dr4_RQlOkqCClBW6W1ztLDM462F4gPfWb4I_6JaRNVXHjNBrpvZHmEfKKwpwCFK83zuh5ASAk0JI_IRNaFkVeVKJ8SiYAtM6Bys_PyPMYvwKAlCAmJK33Q9pgtHGWNX7o7Zcx6GT9MMv00GWLIdmtNcG3VrvsQ_A7DMlizHyfXfgf6LL12MZk05iwuzeavXH2-rBMi9ub3zN2e_Mnv9xYfa3NRjvjB4zTF-Sk1y7iy4d5Sq7O3l425_nq_fJds1jlhpWS5y2vS02N7vu-QFa1Etqe1TXDjqIWumNcCOwEr2vOGFRSc8Mr2THR0VoYVrFTMj3e3QX_fcSY1NZGg87pAf0YleBVIUtaw4GcH8nDqzEG7NUu2K0Oe0VB3dVVd3XVY92DII_CT-tw_x9ana-axb9ufnRtTPjr0dXhm6oEE6X6dLFUa7k8-7h-U6qK_QVKlJCb</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>746295180</pqid></control><display><type>article</type><title>Synthesis, Configuration, and Antimicrobial Properties of Novel Substituted and Cyclized '2′,3″-Thiazachalcones'</title><source>Access via Wiley Online Library</source><creator>Usta, Asu ; Yaşar, Ahmet ; Yılmaz, Nagihan ; Güleç, Canan ; Yaylı, Nuran ; Karaoğlu, Şengül Alpay ; Yaylı, Nurettin</creator><creatorcontrib>Usta, Asu ; Yaşar, Ahmet ; Yılmaz, Nagihan ; Güleç, Canan ; Yaylı, Nuran ; Karaoğlu, Şengül Alpay ; Yaylı, Nurettin</creatorcontrib><description>Nine new thiazachalcone‐based drugs, compounds 1–9, were prepared and fully characterized. The configurations of the photochemical‐dimerization products 7–9 were rationalized by semi‐empirical calculations. Both the experimental data and the theoretical calculations showed that the δ‐truxinic acid type dimer is the most stable isomer of all. All compounds were tested for their antibacterial and antifungal activities. The N‐alkylated congeners 4–6 showed strong antimicrobial activities against various bacteria and a yeast‐like fungus. The MIC and MBC values were as low as 0.1 μg/ml. All the compounds were active against the Gram‐positive bacterium Staphylococcus aureus.</description><identifier>ISSN: 0018-019X</identifier><identifier>EISSN: 1522-2675</identifier><identifier>DOI: 10.1002/hlca.200790154</identifier><language>eng</language><publisher>Zürich: WILEY-VCH Verlag</publisher><subject>2 ; 2′,2″‐Thiazachalcones ; 2″-Thiazachalcones ; Antimicrobial activity ; Photodimerization ; Staphylococcus aureus</subject><ispartof>Helvetica chimica acta, 2007-08, Vol.90 (8), p.1482-1490</ispartof><rights>Copyright © 2007 Verlag Helvetica Chimica Acta AG, Zürich, Switzerland</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3594-b485a1cafff2e36b90bf3883ed1ea7ad3477ed7488433069a4c469d37d187c363</citedby><cites>FETCH-LOGICAL-c3594-b485a1cafff2e36b90bf3883ed1ea7ad3477ed7488433069a4c469d37d187c363</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fhlca.200790154$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fhlca.200790154$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids></links><search><creatorcontrib>Usta, Asu</creatorcontrib><creatorcontrib>Yaşar, Ahmet</creatorcontrib><creatorcontrib>Yılmaz, Nagihan</creatorcontrib><creatorcontrib>Güleç, Canan</creatorcontrib><creatorcontrib>Yaylı, Nuran</creatorcontrib><creatorcontrib>Karaoğlu, Şengül Alpay</creatorcontrib><creatorcontrib>Yaylı, Nurettin</creatorcontrib><title>Synthesis, Configuration, and Antimicrobial Properties of Novel Substituted and Cyclized '2′,3″-Thiazachalcones'</title><title>Helvetica chimica acta</title><addtitle>HCA</addtitle><description>Nine new thiazachalcone‐based drugs, compounds 1–9, were prepared and fully characterized. The configurations of the photochemical‐dimerization products 7–9 were rationalized by semi‐empirical calculations. Both the experimental data and the theoretical calculations showed that the δ‐truxinic acid type dimer is the most stable isomer of all. All compounds were tested for their antibacterial and antifungal activities. The N‐alkylated congeners 4–6 showed strong antimicrobial activities against various bacteria and a yeast‐like fungus. The MIC and MBC values were as low as 0.1 μg/ml. All the compounds were active against the Gram‐positive bacterium Staphylococcus aureus.</description><subject>2</subject><subject>2′,2″‐Thiazachalcones</subject><subject>2″-Thiazachalcones</subject><subject>Antimicrobial activity</subject><subject>Photodimerization</subject><subject>Staphylococcus aureus</subject><issn>0018-019X</issn><issn>1522-2675</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2007</creationdate><recordtype>article</recordtype><recordid>eNqFkMFuEzEQQC1EJULhynlvuWTDeO1dr4_RQlOkqCClBW6W1ztLDM462F4gPfWb4I_6JaRNVXHjNBrpvZHmEfKKwpwCFK83zuh5ASAk0JI_IRNaFkVeVKJ8SiYAtM6Bys_PyPMYvwKAlCAmJK33Q9pgtHGWNX7o7Zcx6GT9MMv00GWLIdmtNcG3VrvsQ_A7DMlizHyfXfgf6LL12MZk05iwuzeavXH2-rBMi9ub3zN2e_Mnv9xYfa3NRjvjB4zTF-Sk1y7iy4d5Sq7O3l425_nq_fJds1jlhpWS5y2vS02N7vu-QFa1Etqe1TXDjqIWumNcCOwEr2vOGFRSc8Mr2THR0VoYVrFTMj3e3QX_fcSY1NZGg87pAf0YleBVIUtaw4GcH8nDqzEG7NUu2K0Oe0VB3dVVd3XVY92DII_CT-tw_x9ana-axb9ufnRtTPjr0dXhm6oEE6X6dLFUa7k8-7h-U6qK_QVKlJCb</recordid><startdate>200708</startdate><enddate>200708</enddate><creator>Usta, Asu</creator><creator>Yaşar, Ahmet</creator><creator>Yılmaz, Nagihan</creator><creator>Güleç, Canan</creator><creator>Yaylı, Nuran</creator><creator>Karaoğlu, Şengül Alpay</creator><creator>Yaylı, Nurettin</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><scope>BSCLL</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7QO</scope><scope>7T7</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>M7N</scope><scope>P64</scope></search><sort><creationdate>200708</creationdate><title>Synthesis, Configuration, and Antimicrobial Properties of Novel Substituted and Cyclized '2′,3″-Thiazachalcones'</title><author>Usta, Asu ; Yaşar, Ahmet ; Yılmaz, Nagihan ; Güleç, Canan ; Yaylı, Nuran ; Karaoğlu, Şengül Alpay ; Yaylı, Nurettin</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3594-b485a1cafff2e36b90bf3883ed1ea7ad3477ed7488433069a4c469d37d187c363</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2007</creationdate><topic>2</topic><topic>2′,2″‐Thiazachalcones</topic><topic>2″-Thiazachalcones</topic><topic>Antimicrobial activity</topic><topic>Photodimerization</topic><topic>Staphylococcus aureus</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Usta, Asu</creatorcontrib><creatorcontrib>Yaşar, Ahmet</creatorcontrib><creatorcontrib>Yılmaz, Nagihan</creatorcontrib><creatorcontrib>Güleç, Canan</creatorcontrib><creatorcontrib>Yaylı, Nuran</creatorcontrib><creatorcontrib>Karaoğlu, Şengül Alpay</creatorcontrib><creatorcontrib>Yaylı, Nurettin</creatorcontrib><collection>Istex</collection><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Industrial and Applied Microbiology Abstracts (Microbiology A)</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>Algology Mycology and Protozoology Abstracts (Microbiology C)</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Helvetica chimica acta</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Usta, Asu</au><au>Yaşar, Ahmet</au><au>Yılmaz, Nagihan</au><au>Güleç, Canan</au><au>Yaylı, Nuran</au><au>Karaoğlu, Şengül Alpay</au><au>Yaylı, Nurettin</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis, Configuration, and Antimicrobial Properties of Novel Substituted and Cyclized '2′,3″-Thiazachalcones'</atitle><jtitle>Helvetica chimica acta</jtitle><addtitle>HCA</addtitle><date>2007-08</date><risdate>2007</risdate><volume>90</volume><issue>8</issue><spage>1482</spage><epage>1490</epage><pages>1482-1490</pages><issn>0018-019X</issn><eissn>1522-2675</eissn><abstract>Nine new thiazachalcone‐based drugs, compounds 1–9, were prepared and fully characterized. The configurations of the photochemical‐dimerization products 7–9 were rationalized by semi‐empirical calculations. Both the experimental data and the theoretical calculations showed that the δ‐truxinic acid type dimer is the most stable isomer of all. All compounds were tested for their antibacterial and antifungal activities. The N‐alkylated congeners 4–6 showed strong antimicrobial activities against various bacteria and a yeast‐like fungus. The MIC and MBC values were as low as 0.1 μg/ml. All the compounds were active against the Gram‐positive bacterium Staphylococcus aureus.</abstract><cop>Zürich</cop><pub>WILEY-VCH Verlag</pub><doi>10.1002/hlca.200790154</doi><tpages>9</tpages></addata></record>
fulltext fulltext
identifier ISSN: 0018-019X
ispartof Helvetica chimica acta, 2007-08, Vol.90 (8), p.1482-1490
issn 0018-019X
1522-2675
language eng
recordid cdi_proquest_miscellaneous_746295180
source Access via Wiley Online Library
subjects 2
2′,2″‐Thiazachalcones
2″-Thiazachalcones
Antimicrobial activity
Photodimerization
Staphylococcus aureus
title Synthesis, Configuration, and Antimicrobial Properties of Novel Substituted and Cyclized '2′,3″-Thiazachalcones'
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-21T13%3A25%3A08IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Synthesis,%20Configuration,%20and%20Antimicrobial%20Properties%20of%20Novel%20Substituted%20and%20Cyclized%20'2%E2%80%B2,3%E2%80%B3-Thiazachalcones'&rft.jtitle=Helvetica%20chimica%20acta&rft.au=Usta,%20Asu&rft.date=2007-08&rft.volume=90&rft.issue=8&rft.spage=1482&rft.epage=1490&rft.pages=1482-1490&rft.issn=0018-019X&rft.eissn=1522-2675&rft_id=info:doi/10.1002/hlca.200790154&rft_dat=%3Cproquest_cross%3E746295180%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=746295180&rft_id=info:pmid/&rfr_iscdi=true