Synthesis, characterization, carbonic anhydrase inhibitor activity, and docking studies of phenylthiazol-2(3h)-ylidene-isoquinoline-5-amine Derivatives

Phenylthiazol-2(3h)-ylidene-isoquinoline-5-amine derivatives(5a-r) were easily prepared from 5-aminoisoquinoline, thioisocyanate, and phenacyl bromide derivatives in the presence of triethylamine in tetrahydrofuran (THF), and dimethyl formamide (DMF) in two steps. In the first step, thiourea was syn...

Full description

Saved in:
Bibliographic Details
Published in:Journal of molecular structure 2023-11, Vol.1291, p.136061, Article 136061
Main Authors: Berber, Nurcan, Şahutoğlu, Arif Sercan, Gökçe, Başak, Çıkrıkçı, Kübra, Gençer, Nahit
Format: Article
Language:English
Subjects:
Carbonic anhydrase
Enzyme inhibitor
Isoquinoline
Thiazole
Thiourea
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-c360t-6c98d1b0915e67f7d7ad41bedd3c5df8a4b1f91e8e30af3bff5477b7d9b434903
cites cdi_FETCH-LOGICAL-c360t-6c98d1b0915e67f7d7ad41bedd3c5df8a4b1f91e8e30af3bff5477b7d9b434903
container_end_page
container_issue
container_start_page 136061
container_title Journal of molecular structure
container_volume 1291
creator Berber, Nurcan
Şahutoğlu, Arif Sercan
Gökçe, Başak
Çıkrıkçı, Kübra
Gençer, Nahit
description Phenylthiazol-2(3h)-ylidene-isoquinoline-5-amine derivatives(5a-r) were easily prepared from 5-aminoisoquinoline, thioisocyanate, and phenacyl bromide derivatives in the presence of triethylamine in tetrahydrofuran (THF), and dimethyl formamide (DMF) in two steps. In the first step, thiourea was synthesized in THF reflux, 24 h and then in the second step, the formation of thiazole ring was ensured in EtOH-DMF (5:5 v/v), reflux, 24 h. The newly synthesized compounds were characterized using 1H NMR, 13C NMR, IR, and elemental analysis. The inhibitory effects of 18 newly synthesized compounds (5a-r) on hydratase and esterase activities of carbonic anhydrase isoenzymes (hCA I, II, IX, and X) were studied in vitro. [Display omitted]
doi_str_mv 10.1016/j.molstruc.2023.136061
format article
fullrecord <record><control><sourceid>elsevier_cross</sourceid><recordid>TN_cdi_crossref_primary_10_1016_j_molstruc_2023_136061</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><els_id>S0022286023011547</els_id><sourcerecordid>S0022286023011547</sourcerecordid><originalsourceid>FETCH-LOGICAL-c360t-6c98d1b0915e67f7d7ad41bedd3c5df8a4b1f91e8e30af3bff5477b7d9b434903</originalsourceid><addsrcrecordid>eNqFUMtO5DAQtBBIzAK_gHxcJDzYSSaP2yLeEhIH4Gw5dpv0kLHB9owUfoTfxWjYM6dSP6qquwg5FnwuuKjPlvOVH2MKaz0veFHORVnzWuyQmWibgrVcVLtkxnlRsKKt-T75E-OScy4yeUY-HyeXBogYT6keVFA6QcAPldC73FGh9w41VW6YTFARKLoBe0w-0LyKG0zTaZ4aarx-RfdCY1obhEi9pW8DuGlMA6oPP7LibzmcsGlEAw4YRv--RudHzMWCqVVGepmtN9l6A_GQ7Fk1Rjj6wQPyfH31dHHL7h9u7i7O75nOXyZW6641ouedWEDd2MY0ylSiB2NKvTC2VVUvbCeghZIrW_bWLqqm6RvT9VVZdbw8IPVWVwcfYwAr3wKuVJik4PI7XrmU_-OV3_HKbbyZ-G9LhHzdBiHIqBGcBoMBdJLG428SX2eSjGY</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>Synthesis, characterization, carbonic anhydrase inhibitor activity, and docking studies of phenylthiazol-2(3h)-ylidene-isoquinoline-5-amine Derivatives</title><source>Elsevier</source><creator>Berber, Nurcan ; Şahutoğlu, Arif Sercan ; Gökçe, Başak ; Çıkrıkçı, Kübra ; Gençer, Nahit</creator><creatorcontrib>Berber, Nurcan ; Şahutoğlu, Arif Sercan ; Gökçe, Başak ; Çıkrıkçı, Kübra ; Gençer, Nahit</creatorcontrib><description>Phenylthiazol-2(3h)-ylidene-isoquinoline-5-amine derivatives(5a-r) were easily prepared from 5-aminoisoquinoline, thioisocyanate, and phenacyl bromide derivatives in the presence of triethylamine in tetrahydrofuran (THF), and dimethyl formamide (DMF) in two steps. In the first step, thiourea was synthesized in THF reflux, 24 h and then in the second step, the formation of thiazole ring was ensured in EtOH-DMF (5:5 v/v), reflux, 24 h. The newly synthesized compounds were characterized using 1H NMR, 13C NMR, IR, and elemental analysis. The inhibitory effects of 18 newly synthesized compounds (5a-r) on hydratase and esterase activities of carbonic anhydrase isoenzymes (hCA I, II, IX, and X) were studied in vitro. [Display omitted]</description><identifier>ISSN: 0022-2860</identifier><identifier>EISSN: 1872-8014</identifier><identifier>DOI: 10.1016/j.molstruc.2023.136061</identifier><language>eng</language><publisher>Elsevier B.V</publisher><subject>Carbonic anhydrase ; Enzyme inhibitor ; Isoquinoline ; Thiazole ; Thiourea</subject><ispartof>Journal of molecular structure, 2023-11, Vol.1291, p.136061, Article 136061</ispartof><rights>2023 Elsevier B.V.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c360t-6c98d1b0915e67f7d7ad41bedd3c5df8a4b1f91e8e30af3bff5477b7d9b434903</citedby><cites>FETCH-LOGICAL-c360t-6c98d1b0915e67f7d7ad41bedd3c5df8a4b1f91e8e30af3bff5477b7d9b434903</cites></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>Berber, Nurcan</creatorcontrib><creatorcontrib>Şahutoğlu, Arif Sercan</creatorcontrib><creatorcontrib>Gökçe, Başak</creatorcontrib><creatorcontrib>Çıkrıkçı, Kübra</creatorcontrib><creatorcontrib>Gençer, Nahit</creatorcontrib><title>Synthesis, characterization, carbonic anhydrase inhibitor activity, and docking studies of phenylthiazol-2(3h)-ylidene-isoquinoline-5-amine Derivatives</title><title>Journal of molecular structure</title><description>Phenylthiazol-2(3h)-ylidene-isoquinoline-5-amine derivatives(5a-r) were easily prepared from 5-aminoisoquinoline, thioisocyanate, and phenacyl bromide derivatives in the presence of triethylamine in tetrahydrofuran (THF), and dimethyl formamide (DMF) in two steps. In the first step, thiourea was synthesized in THF reflux, 24 h and then in the second step, the formation of thiazole ring was ensured in EtOH-DMF (5:5 v/v), reflux, 24 h. The newly synthesized compounds were characterized using 1H NMR, 13C NMR, IR, and elemental analysis. The inhibitory effects of 18 newly synthesized compounds (5a-r) on hydratase and esterase activities of carbonic anhydrase isoenzymes (hCA I, II, IX, and X) were studied in vitro. [Display omitted]</description><subject>Carbonic anhydrase</subject><subject>Enzyme inhibitor</subject><subject>Isoquinoline</subject><subject>Thiazole</subject><subject>Thiourea</subject><issn>0022-2860</issn><issn>1872-8014</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNqFUMtO5DAQtBBIzAK_gHxcJDzYSSaP2yLeEhIH4Gw5dpv0kLHB9owUfoTfxWjYM6dSP6qquwg5FnwuuKjPlvOVH2MKaz0veFHORVnzWuyQmWibgrVcVLtkxnlRsKKt-T75E-OScy4yeUY-HyeXBogYT6keVFA6QcAPldC73FGh9w41VW6YTFARKLoBe0w-0LyKG0zTaZ4aarx-RfdCY1obhEi9pW8DuGlMA6oPP7LibzmcsGlEAw4YRv--RudHzMWCqVVGepmtN9l6A_GQ7Fk1Rjj6wQPyfH31dHHL7h9u7i7O75nOXyZW6641ouedWEDd2MY0ylSiB2NKvTC2VVUvbCeghZIrW_bWLqqm6RvT9VVZdbw8IPVWVwcfYwAr3wKuVJik4PI7XrmU_-OV3_HKbbyZ-G9LhHzdBiHIqBGcBoMBdJLG428SX2eSjGY</recordid><startdate>20231105</startdate><enddate>20231105</enddate><creator>Berber, Nurcan</creator><creator>Şahutoğlu, Arif Sercan</creator><creator>Gökçe, Başak</creator><creator>Çıkrıkçı, Kübra</creator><creator>Gençer, Nahit</creator><general>Elsevier B.V</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20231105</creationdate><title>Synthesis, characterization, carbonic anhydrase inhibitor activity, and docking studies of phenylthiazol-2(3h)-ylidene-isoquinoline-5-amine Derivatives</title><author>Berber, Nurcan ; Şahutoğlu, Arif Sercan ; Gökçe, Başak ; Çıkrıkçı, Kübra ; Gençer, Nahit</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c360t-6c98d1b0915e67f7d7ad41bedd3c5df8a4b1f91e8e30af3bff5477b7d9b434903</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Carbonic anhydrase</topic><topic>Enzyme inhibitor</topic><topic>Isoquinoline</topic><topic>Thiazole</topic><topic>Thiourea</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Berber, Nurcan</creatorcontrib><creatorcontrib>Şahutoğlu, Arif Sercan</creatorcontrib><creatorcontrib>Gökçe, Başak</creatorcontrib><creatorcontrib>Çıkrıkçı, Kübra</creatorcontrib><creatorcontrib>Gençer, Nahit</creatorcontrib><collection>CrossRef</collection><jtitle>Journal of molecular structure</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Berber, Nurcan</au><au>Şahutoğlu, Arif Sercan</au><au>Gökçe, Başak</au><au>Çıkrıkçı, Kübra</au><au>Gençer, Nahit</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis, characterization, carbonic anhydrase inhibitor activity, and docking studies of phenylthiazol-2(3h)-ylidene-isoquinoline-5-amine Derivatives</atitle><jtitle>Journal of molecular structure</jtitle><date>2023-11-05</date><risdate>2023</risdate><volume>1291</volume><spage>136061</spage><pages>136061-</pages><artnum>136061</artnum><issn>0022-2860</issn><eissn>1872-8014</eissn><abstract>Phenylthiazol-2(3h)-ylidene-isoquinoline-5-amine derivatives(5a-r) were easily prepared from 5-aminoisoquinoline, thioisocyanate, and phenacyl bromide derivatives in the presence of triethylamine in tetrahydrofuran (THF), and dimethyl formamide (DMF) in two steps. In the first step, thiourea was synthesized in THF reflux, 24 h and then in the second step, the formation of thiazole ring was ensured in EtOH-DMF (5:5 v/v), reflux, 24 h. The newly synthesized compounds were characterized using 1H NMR, 13C NMR, IR, and elemental analysis. The inhibitory effects of 18 newly synthesized compounds (5a-r) on hydratase and esterase activities of carbonic anhydrase isoenzymes (hCA I, II, IX, and X) were studied in vitro. [Display omitted]</abstract><pub>Elsevier B.V</pub><doi>10.1016/j.molstruc.2023.136061</doi><oa>free_for_read</oa></addata></record>
fulltext fulltext
identifier ISSN: 0022-2860
ispartof Journal of molecular structure, 2023-11, Vol.1291, p.136061, Article 136061
issn 0022-2860
1872-8014
language eng
recordid cdi_crossref_primary_10_1016_j_molstruc_2023_136061
source Elsevier
subjects Carbonic anhydrase
Enzyme inhibitor
Isoquinoline
Thiazole
Thiourea
title Synthesis, characterization, carbonic anhydrase inhibitor activity, and docking studies of phenylthiazol-2(3h)-ylidene-isoquinoline-5-amine Derivatives
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-28T21%3A24%3A24IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-elsevier_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Synthesis,%20characterization,%20carbonic%20anhydrase%20inhibitor%20activity,%20and%20docking%20studies%20of%20phenylthiazol-2(3h)-ylidene-isoquinoline-5-amine%20Derivatives&rft.jtitle=Journal%20of%20molecular%20structure&rft.au=Berber,%20Nurcan&rft.date=2023-11-05&rft.volume=1291&rft.spage=136061&rft.pages=136061-&rft.artnum=136061&rft.issn=0022-2860&rft.eissn=1872-8014&rft_id=info:doi/10.1016/j.molstruc.2023.136061&rft_dat=%3Celsevier_cross%3ES0022286023011547%3C/elsevier_cross%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-c360t-6c98d1b0915e67f7d7ad41bedd3c5df8a4b1f91e8e30af3bff5477b7d9b434903%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_id=info:pmid/&rfr_iscdi=true