Synthesis and Biological Evaluation of Quinazoline-4-thiones

Several 2,2-dimethyl-3-phenyl-1,2-dihydroquinazoline-4(3H)-thiones and 2-methyl-3-phenylquinazoline-4(3H)-thiones were synthesized and tested for their antimycobacterial, photosynthesis-inhibiting, and antialgal activity. Antimycobacterially active compounds were found among the 6-chloro substituted...

Full description

Saved in:
Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2003-11, Vol.8 (11), p.756-769
Main Authors: Kubicová, Lenka, Šustr, Martin, Kráľová, Katarína, Chobot, Vladimír, Vytlačilová, Jitka, Jahodář, Luděk, Vuorela, Pia, Macháček, Miloš, Kaustová, Jarmila
Format: Article
Language:English
Subjects:
alga
Artemia salina
Bioassays
Chloroplasts
mycobacteria
Pharmacy
Photosynthesis
photosynthesis-inhibiting activity
Quinazoline-4-thiones
toxicological screening
Tuberculosis
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
cited_by cdi_FETCH-LOGICAL-c474t-eaa030b1b180c044d86bcbd925db637dbfbc3f2a19ad11f295e20627296974c93
cites cdi_FETCH-LOGICAL-c474t-eaa030b1b180c044d86bcbd925db637dbfbc3f2a19ad11f295e20627296974c93
container_end_page 769
container_issue 11
container_start_page 756
container_title Molecules (Basel, Switzerland)
container_volume 8
creator Kubicová, Lenka
Šustr, Martin
Kráľová, Katarína
Chobot, Vladimír
Vytlačilová, Jitka
Jahodář, Luděk
Vuorela, Pia
Macháček, Miloš
Kaustová, Jarmila
description Several 2,2-dimethyl-3-phenyl-1,2-dihydroquinazoline-4(3H)-thiones and 2-methyl-3-phenylquinazoline-4(3H)-thiones were synthesized and tested for their antimycobacterial, photosynthesis-inhibiting, and antialgal activity. Antimycobacterially active compounds were found among the 6-chloro substituted compounds. 6-Chloro-3-(4-isopropylphenyl)-2-methylquinazoline-4(3H)-thione exhibited higher activity than the isoniazid standard against Mycobacterium avium and M. kansasii. Most of the compounds possessed photosynthesis-inhibiting activity. 6-Chloro-2,2-dimethyl-3-phenyl-1,2-dihydroquinazoline-4(3H)-thione and its 3´-chloro- and 3´,4´-dichloro analogs were most effective in the inhibition of oxygen evolution rate in spinach chloroplasts. Of compounds selected for toxicological screening, 6-chloro-3-(4-isopropylphenyl)-2-methyl-quinazoline-4(3H)-thione was the only one active in the brine shrimp bioassay.
doi_str_mv 10.3390/81100756
format article
fullrecord <record><control><sourceid>proquest_doaj_</sourceid><recordid>TN_cdi_doaj_primary_oai_doaj_org_article_a1ca30281a404bce8d77427591625b70</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><doaj_id>oai_doaj_org_article_a1ca30281a404bce8d77427591625b70</doaj_id><sourcerecordid>3321802591</sourcerecordid><originalsourceid>FETCH-LOGICAL-c474t-eaa030b1b180c044d86bcbd925db637dbfbc3f2a19ad11f295e20627296974c93</originalsourceid><addsrcrecordid>eNpVkV9LHTEQxRdRqFqhH2HBF1_WziTZZAMitKKtIJTS-hwmf_beXNaNJruCfnq3Xlvq0wxnDr_hcKrqE8Ip5xo-d4gAqpU71T4KBg0HoXf_2z9UB6VsABgKbPers19P47QOJZaaRl9_jWlIq-hoqC8faZhpimmsU1__nONIz2mIY2hEM60XOZSP1V5PQwlHb_Owur26_H3xvbn58e364stN44QSUxOIgINFix04EMJ30jrrNWu9lVx521vHe0aoySP2TLeBgWSKaamVcJofVtdbrk-0Mfc53lF-MomieRVSXhnKU3RDMISOOLAOSYCwLnReKcFUq1Gy1ipYWOdb1v1s74J3YZwyDe-g7y9jXJtVejQShdSCLYDjN0BOD3Mok9mkOY9LfoMtR9BaSrG4TrYul1MpOfT_PiCYP0WZv0XxFze8hBc</addsrcrecordid><sourcetype>Open Website</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1531099664</pqid></control><display><type>article</type><title>Synthesis and Biological Evaluation of Quinazoline-4-thiones</title><source>PubMed (Medline)</source><source>Publicly Available Content Database (Proquest) (PQ_SDU_P3)</source><creator>Kubicová, Lenka ; Šustr, Martin ; Kráľová, Katarína ; Chobot, Vladimír ; Vytlačilová, Jitka ; Jahodář, Luděk ; Vuorela, Pia ; Macháček, Miloš ; Kaustová, Jarmila</creator><creatorcontrib>Kubicová, Lenka ; Šustr, Martin ; Kráľová, Katarína ; Chobot, Vladimír ; Vytlačilová, Jitka ; Jahodář, Luděk ; Vuorela, Pia ; Macháček, Miloš ; Kaustová, Jarmila</creatorcontrib><description>Several 2,2-dimethyl-3-phenyl-1,2-dihydroquinazoline-4(3H)-thiones and 2-methyl-3-phenylquinazoline-4(3H)-thiones were synthesized and tested for their antimycobacterial, photosynthesis-inhibiting, and antialgal activity. Antimycobacterially active compounds were found among the 6-chloro substituted compounds. 6-Chloro-3-(4-isopropylphenyl)-2-methylquinazoline-4(3H)-thione exhibited higher activity than the isoniazid standard against Mycobacterium avium and M. kansasii. Most of the compounds possessed photosynthesis-inhibiting activity. 6-Chloro-2,2-dimethyl-3-phenyl-1,2-dihydroquinazoline-4(3H)-thione and its 3´-chloro- and 3´,4´-dichloro analogs were most effective in the inhibition of oxygen evolution rate in spinach chloroplasts. Of compounds selected for toxicological screening, 6-chloro-3-(4-isopropylphenyl)-2-methyl-quinazoline-4(3H)-thione was the only one active in the brine shrimp bioassay.</description><identifier>ISSN: 1420-3049</identifier><identifier>EISSN: 1420-3049</identifier><identifier>DOI: 10.3390/81100756</identifier><language>eng</language><publisher>Basel: MDPI AG</publisher><subject>alga ; Artemia salina ; Bioassays ; Chloroplasts ; mycobacteria ; Pharmacy ; Photosynthesis ; photosynthesis-inhibiting activity ; Quinazoline-4-thiones ; toxicological screening ; Tuberculosis</subject><ispartof>Molecules (Basel, Switzerland), 2003-11, Vol.8 (11), p.756-769</ispartof><rights>Copyright MDPI AG 2003</rights><rights>2003 by MDPI 2003</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c474t-eaa030b1b180c044d86bcbd925db637dbfbc3f2a19ad11f295e20627296974c93</citedby><cites>FETCH-LOGICAL-c474t-eaa030b1b180c044d86bcbd925db637dbfbc3f2a19ad11f295e20627296974c93</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.proquest.com/docview/1531099664/fulltextPDF?pq-origsite=primo$$EPDF$$P50$$Gproquest$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.proquest.com/docview/1531099664?pq-origsite=primo$$EHTML$$P50$$Gproquest$$Hfree_for_read</linktohtml><link.rule.ids>230,314,727,780,784,885,25753,27924,27925,37012,44590,53791,53793,75126</link.rule.ids></links><search><creatorcontrib>Kubicová, Lenka</creatorcontrib><creatorcontrib>Šustr, Martin</creatorcontrib><creatorcontrib>Kráľová, Katarína</creatorcontrib><creatorcontrib>Chobot, Vladimír</creatorcontrib><creatorcontrib>Vytlačilová, Jitka</creatorcontrib><creatorcontrib>Jahodář, Luděk</creatorcontrib><creatorcontrib>Vuorela, Pia</creatorcontrib><creatorcontrib>Macháček, Miloš</creatorcontrib><creatorcontrib>Kaustová, Jarmila</creatorcontrib><title>Synthesis and Biological Evaluation of Quinazoline-4-thiones</title><title>Molecules (Basel, Switzerland)</title><description>Several 2,2-dimethyl-3-phenyl-1,2-dihydroquinazoline-4(3H)-thiones and 2-methyl-3-phenylquinazoline-4(3H)-thiones were synthesized and tested for their antimycobacterial, photosynthesis-inhibiting, and antialgal activity. Antimycobacterially active compounds were found among the 6-chloro substituted compounds. 6-Chloro-3-(4-isopropylphenyl)-2-methylquinazoline-4(3H)-thione exhibited higher activity than the isoniazid standard against Mycobacterium avium and M. kansasii. Most of the compounds possessed photosynthesis-inhibiting activity. 6-Chloro-2,2-dimethyl-3-phenyl-1,2-dihydroquinazoline-4(3H)-thione and its 3´-chloro- and 3´,4´-dichloro analogs were most effective in the inhibition of oxygen evolution rate in spinach chloroplasts. Of compounds selected for toxicological screening, 6-chloro-3-(4-isopropylphenyl)-2-methyl-quinazoline-4(3H)-thione was the only one active in the brine shrimp bioassay.</description><subject>alga</subject><subject>Artemia salina</subject><subject>Bioassays</subject><subject>Chloroplasts</subject><subject>mycobacteria</subject><subject>Pharmacy</subject><subject>Photosynthesis</subject><subject>photosynthesis-inhibiting activity</subject><subject>Quinazoline-4-thiones</subject><subject>toxicological screening</subject><subject>Tuberculosis</subject><issn>1420-3049</issn><issn>1420-3049</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2003</creationdate><recordtype>article</recordtype><sourceid>PIMPY</sourceid><sourceid>DOA</sourceid><recordid>eNpVkV9LHTEQxRdRqFqhH2HBF1_WziTZZAMitKKtIJTS-hwmf_beXNaNJruCfnq3Xlvq0wxnDr_hcKrqE8Ip5xo-d4gAqpU71T4KBg0HoXf_2z9UB6VsABgKbPers19P47QOJZaaRl9_jWlIq-hoqC8faZhpimmsU1__nONIz2mIY2hEM60XOZSP1V5PQwlHb_Owur26_H3xvbn58e364stN44QSUxOIgINFix04EMJ30jrrNWu9lVx521vHe0aoySP2TLeBgWSKaamVcJofVtdbrk-0Mfc53lF-MomieRVSXhnKU3RDMISOOLAOSYCwLnReKcFUq1Gy1ipYWOdb1v1s74J3YZwyDe-g7y9jXJtVejQShdSCLYDjN0BOD3Mok9mkOY9LfoMtR9BaSrG4TrYul1MpOfT_PiCYP0WZv0XxFze8hBc</recordid><startdate>20031115</startdate><enddate>20031115</enddate><creator>Kubicová, Lenka</creator><creator>Šustr, Martin</creator><creator>Kráľová, Katarína</creator><creator>Chobot, Vladimír</creator><creator>Vytlačilová, Jitka</creator><creator>Jahodář, Luděk</creator><creator>Vuorela, Pia</creator><creator>Macháček, Miloš</creator><creator>Kaustová, Jarmila</creator><general>MDPI AG</general><general>MDPI</general><scope>AAYXX</scope><scope>CITATION</scope><scope>3V.</scope><scope>7X7</scope><scope>7XB</scope><scope>88E</scope><scope>8FI</scope><scope>8FJ</scope><scope>8FK</scope><scope>ABUWG</scope><scope>AFKRA</scope><scope>AZQEC</scope><scope>BENPR</scope><scope>CCPQU</scope><scope>DWQXO</scope><scope>FYUFA</scope><scope>GHDGH</scope><scope>K9.</scope><scope>M0S</scope><scope>M1P</scope><scope>PIMPY</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>PRINS</scope><scope>5PM</scope><scope>DOA</scope></search><sort><creationdate>20031115</creationdate><title>Synthesis and Biological Evaluation of Quinazoline-4-thiones</title><author>Kubicová, Lenka ; Šustr, Martin ; Kráľová, Katarína ; Chobot, Vladimír ; Vytlačilová, Jitka ; Jahodář, Luděk ; Vuorela, Pia ; Macháček, Miloš ; Kaustová, Jarmila</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c474t-eaa030b1b180c044d86bcbd925db637dbfbc3f2a19ad11f295e20627296974c93</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2003</creationdate><topic>alga</topic><topic>Artemia salina</topic><topic>Bioassays</topic><topic>Chloroplasts</topic><topic>mycobacteria</topic><topic>Pharmacy</topic><topic>Photosynthesis</topic><topic>photosynthesis-inhibiting activity</topic><topic>Quinazoline-4-thiones</topic><topic>toxicological screening</topic><topic>Tuberculosis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kubicová, Lenka</creatorcontrib><creatorcontrib>Šustr, Martin</creatorcontrib><creatorcontrib>Kráľová, Katarína</creatorcontrib><creatorcontrib>Chobot, Vladimír</creatorcontrib><creatorcontrib>Vytlačilová, Jitka</creatorcontrib><creatorcontrib>Jahodář, Luděk</creatorcontrib><creatorcontrib>Vuorela, Pia</creatorcontrib><creatorcontrib>Macháček, Miloš</creatorcontrib><creatorcontrib>Kaustová, Jarmila</creatorcontrib><collection>CrossRef</collection><collection>ProQuest Central (Corporate)</collection><collection>ProQuest Health &amp; Medical Collection</collection><collection>ProQuest Central (purchase pre-March 2016)</collection><collection>Medical Database (Alumni Edition)</collection><collection>Hospital Premium Collection</collection><collection>Hospital Premium Collection (Alumni Edition)</collection><collection>ProQuest Central (Alumni) (purchase pre-March 2016)</collection><collection>ProQuest Central (Alumni)</collection><collection>ProQuest Central</collection><collection>ProQuest Central Essentials</collection><collection>AUTh Library subscriptions: ProQuest Central</collection><collection>ProQuest One Community College</collection><collection>ProQuest Central Korea</collection><collection>Health Research Premium Collection</collection><collection>Health Research Premium Collection (Alumni)</collection><collection>ProQuest Health &amp; Medical Complete (Alumni)</collection><collection>Health &amp; Medical Collection (Alumni Edition)</collection><collection>PML(ProQuest Medical Library)</collection><collection>Publicly Available Content Database (Proquest) (PQ_SDU_P3)</collection><collection>ProQuest One Academic Eastern Edition (DO NOT USE)</collection><collection>ProQuest One Academic</collection><collection>ProQuest One Academic UKI Edition</collection><collection>ProQuest Central China</collection><collection>PubMed Central (Full Participant titles)</collection><collection>DOAJ Directory of Open Access Journals</collection><jtitle>Molecules (Basel, Switzerland)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kubicová, Lenka</au><au>Šustr, Martin</au><au>Kráľová, Katarína</au><au>Chobot, Vladimír</au><au>Vytlačilová, Jitka</au><au>Jahodář, Luděk</au><au>Vuorela, Pia</au><au>Macháček, Miloš</au><au>Kaustová, Jarmila</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and Biological Evaluation of Quinazoline-4-thiones</atitle><jtitle>Molecules (Basel, Switzerland)</jtitle><date>2003-11-15</date><risdate>2003</risdate><volume>8</volume><issue>11</issue><spage>756</spage><epage>769</epage><pages>756-769</pages><issn>1420-3049</issn><eissn>1420-3049</eissn><abstract>Several 2,2-dimethyl-3-phenyl-1,2-dihydroquinazoline-4(3H)-thiones and 2-methyl-3-phenylquinazoline-4(3H)-thiones were synthesized and tested for their antimycobacterial, photosynthesis-inhibiting, and antialgal activity. Antimycobacterially active compounds were found among the 6-chloro substituted compounds. 6-Chloro-3-(4-isopropylphenyl)-2-methylquinazoline-4(3H)-thione exhibited higher activity than the isoniazid standard against Mycobacterium avium and M. kansasii. Most of the compounds possessed photosynthesis-inhibiting activity. 6-Chloro-2,2-dimethyl-3-phenyl-1,2-dihydroquinazoline-4(3H)-thione and its 3´-chloro- and 3´,4´-dichloro analogs were most effective in the inhibition of oxygen evolution rate in spinach chloroplasts. Of compounds selected for toxicological screening, 6-chloro-3-(4-isopropylphenyl)-2-methyl-quinazoline-4(3H)-thione was the only one active in the brine shrimp bioassay.</abstract><cop>Basel</cop><pub>MDPI AG</pub><doi>10.3390/81100756</doi><tpages>14</tpages><oa>free_for_read</oa></addata></record>
fulltext fulltext
identifier ISSN: 1420-3049
ispartof Molecules (Basel, Switzerland), 2003-11, Vol.8 (11), p.756-769
issn 1420-3049
1420-3049
language eng
recordid cdi_doaj_primary_oai_doaj_org_article_a1ca30281a404bce8d77427591625b70
source PubMed (Medline); Publicly Available Content Database (Proquest) (PQ_SDU_P3)
subjects alga
Artemia salina
Bioassays
Chloroplasts
mycobacteria
Pharmacy
Photosynthesis
photosynthesis-inhibiting activity
Quinazoline-4-thiones
toxicological screening
Tuberculosis
title Synthesis and Biological Evaluation of Quinazoline-4-thiones
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-26T11%3A16%3A10IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_doaj_&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Synthesis%20and%20Biological%20Evaluation%20of%20Quinazoline-4-thiones&rft.jtitle=Molecules%20(Basel,%20Switzerland)&rft.au=Kubicov%C3%A1,%20Lenka&rft.date=2003-11-15&rft.volume=8&rft.issue=11&rft.spage=756&rft.epage=769&rft.pages=756-769&rft.issn=1420-3049&rft.eissn=1420-3049&rft_id=info:doi/10.3390/81100756&rft_dat=%3Cproquest_doaj_%3E3321802591%3C/proquest_doaj_%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-c474t-eaa030b1b180c044d86bcbd925db637dbfbc3f2a19ad11f295e20627296974c93%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=1531099664&rft_id=info:pmid/&rfr_iscdi=true