Refinement of the pharmacophore of 3,4-dihydroquinazoline-2(1 H)-thiones for their anti-melanogenesis activity
In order to define the structural requirements of quinazoline-2(1 H)-thiones 1 for their inhibitory activity on melanogenesis, a novel series of 3,4-dihydroquinazoline-2(1 H)-thiones ( 3a– h) were prepared and screened for their melanogenesis inhibition on melanoma B16 cell line under the stimulant...
Gespeichert in:
| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2010-08, Vol.20 (16), p.4771-4773 |
|---|---|
| Hauptverfasser: | , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 4773 |
|---|---|
| container_issue | 16 |
| container_start_page | 4771 |
| container_title | Bioorganic & medicinal chemistry letters |
| container_volume | 20 |
| creator | Thanigaimalai, Pillaiyar Sharma, Vinay K. Lee, Ki-Cheul Yun, Cheong-Yong Kim, Youngsoo Jung, Sang-Hun |
| description | In order to define the structural requirements of quinazoline-2(1
H)-thiones
1 for their inhibitory activity on melanogenesis, a novel series of 3,4-dihydroquinazoline-2(1
H)-thiones (
3a–
h) were prepared and screened for their melanogenesis inhibition on melanoma B16 cell line under the stimulant of α-MSH. The anti-melanogenesis activity of
3 is mainly mediated by the hydrogen bonding ability of thioamide unit in addition to complexation ability of thione and the hydrophobic binding power of side chain substitutions at 3-position. Thus, the pharmacophore of 3,4-dihydroquinazoline-2(1
H)-thiones for their anti-melanogenesis activity could be refined as 3-hydrophobic substituted quinazolinethione. |
| doi_str_mv | 10.1016/j.bmcl.2010.06.123 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_754566112</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><els_id>S0960894X10009108</els_id><sourcerecordid>749024202</sourcerecordid><originalsourceid>FETCH-LOGICAL-c417t-ed4d93f689c96c78fb28f9e4db56c9681222eaba1be7a42b537f61afce50913</originalsourceid><addsrcrecordid>eNqFkcGL1DAYxYMo7rj6D3iQXkQFM35J07SBvciirrAgqAdvIU2_2AxtMyaZhfGvN2VGvekp8PJ7j8f3CHnKYMuAyTe7bT_bacuhCCC3jNf3yIYJKWgtoLlPNqAk0E6JbxfkUUo7ACZAiIfkgoOsO97Bhiyf0fkFZ1xyFVyVR6z2o4mzsWE_hoirWL8WdPDjcYjhx8Ev5meYioXyl6y6eUXz6MOCqXIhrnYfK7NkT2eczBK-Y_nyqTI2-zufj4_JA2emhE_O7yX58v7d1-sbevvpw8frt7fUCtZmioMYVO1kp6yStu1czzunUAx9I4vSMc45mt6wHlsjeN_UrZPMOIsNKFZfkhen1P3aGFPWs08Wp9IIwyHpthGNlKwc7L-kUMAFh5XkJ9LGkFJEp_fRzyYeNQO9zqF3ep1Dr3NokLqkF9Ozc_yhn3H4Y_l9_wI8PwMmWTO5aBbr01-uBtWpVhTu6sRhOdqdx6iT9bhYHHxEm_UQ_L96_AKzBKk1</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>749024202</pqid></control><display><type>article</type><title>Refinement of the pharmacophore of 3,4-dihydroquinazoline-2(1 H)-thiones for their anti-melanogenesis activity</title><source>MEDLINE</source><source>ScienceDirect Journals (5 years ago - present)</source><creator>Thanigaimalai, Pillaiyar ; Sharma, Vinay K. ; Lee, Ki-Cheul ; Yun, Cheong-Yong ; Kim, Youngsoo ; Jung, Sang-Hun</creator><creatorcontrib>Thanigaimalai, Pillaiyar ; Sharma, Vinay K. ; Lee, Ki-Cheul ; Yun, Cheong-Yong ; Kim, Youngsoo ; Jung, Sang-Hun</creatorcontrib><description>In order to define the structural requirements of quinazoline-2(1
H)-thiones
1 for their inhibitory activity on melanogenesis, a novel series of 3,4-dihydroquinazoline-2(1
H)-thiones (
3a–
h) were prepared and screened for their melanogenesis inhibition on melanoma B16 cell line under the stimulant of α-MSH. The anti-melanogenesis activity of
3 is mainly mediated by the hydrogen bonding ability of thioamide unit in addition to complexation ability of thione and the hydrophobic binding power of side chain substitutions at 3-position. Thus, the pharmacophore of 3,4-dihydroquinazoline-2(1
H)-thiones for their anti-melanogenesis activity could be refined as 3-hydrophobic substituted quinazolinethione.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2010.06.123</identifier><identifier>PMID: 20638280</identifier><language>eng</language><publisher>Amsterdam: Elsevier Ltd</publisher><subject>3,4-Quinazoline-2(1 H)-thiones ; alpha-MSH - antagonists & inhibitors ; alpha-MSH - metabolism ; Animals ; Biological and medical sciences ; Cell Line, Tumor ; Inhibitors ; Medical sciences ; Melanins - biosynthesis ; Melanogenesis ; Mice ; Pharmacology. Drug treatments ; Skin, nail, hair, dermoskeleton ; Structure-Activity Relationship ; Thiones - chemical synthesis ; Thiones - chemistry ; Thiones - therapeutic use</subject><ispartof>Bioorganic & medicinal chemistry letters, 2010-08, Vol.20 (16), p.4771-4773</ispartof><rights>2010</rights><rights>2015 INIST-CNRS</rights><rights>Crown Copyright 2010. Published by Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c417t-ed4d93f689c96c78fb28f9e4db56c9681222eaba1be7a42b537f61afce50913</citedby><cites>FETCH-LOGICAL-c417t-ed4d93f689c96c78fb28f9e4db56c9681222eaba1be7a42b537f61afce50913</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0960894X10009108$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65306</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=23098974$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/20638280$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Thanigaimalai, Pillaiyar</creatorcontrib><creatorcontrib>Sharma, Vinay K.</creatorcontrib><creatorcontrib>Lee, Ki-Cheul</creatorcontrib><creatorcontrib>Yun, Cheong-Yong</creatorcontrib><creatorcontrib>Kim, Youngsoo</creatorcontrib><creatorcontrib>Jung, Sang-Hun</creatorcontrib><title>Refinement of the pharmacophore of 3,4-dihydroquinazoline-2(1 H)-thiones for their anti-melanogenesis activity</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>In order to define the structural requirements of quinazoline-2(1
H)-thiones
1 for their inhibitory activity on melanogenesis, a novel series of 3,4-dihydroquinazoline-2(1
H)-thiones (
3a–
h) were prepared and screened for their melanogenesis inhibition on melanoma B16 cell line under the stimulant of α-MSH. The anti-melanogenesis activity of
3 is mainly mediated by the hydrogen bonding ability of thioamide unit in addition to complexation ability of thione and the hydrophobic binding power of side chain substitutions at 3-position. Thus, the pharmacophore of 3,4-dihydroquinazoline-2(1
H)-thiones for their anti-melanogenesis activity could be refined as 3-hydrophobic substituted quinazolinethione.</description><subject>3,4-Quinazoline-2(1 H)-thiones</subject><subject>alpha-MSH - antagonists & inhibitors</subject><subject>alpha-MSH - metabolism</subject><subject>Animals</subject><subject>Biological and medical sciences</subject><subject>Cell Line, Tumor</subject><subject>Inhibitors</subject><subject>Medical sciences</subject><subject>Melanins - biosynthesis</subject><subject>Melanogenesis</subject><subject>Mice</subject><subject>Pharmacology. Drug treatments</subject><subject>Skin, nail, hair, dermoskeleton</subject><subject>Structure-Activity Relationship</subject><subject>Thiones - chemical synthesis</subject><subject>Thiones - chemistry</subject><subject>Thiones - therapeutic use</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2010</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkcGL1DAYxYMo7rj6D3iQXkQFM35J07SBvciirrAgqAdvIU2_2AxtMyaZhfGvN2VGvekp8PJ7j8f3CHnKYMuAyTe7bT_bacuhCCC3jNf3yIYJKWgtoLlPNqAk0E6JbxfkUUo7ACZAiIfkgoOsO97Bhiyf0fkFZ1xyFVyVR6z2o4mzsWE_hoirWL8WdPDjcYjhx8Ev5meYioXyl6y6eUXz6MOCqXIhrnYfK7NkT2eczBK-Y_nyqTI2-zufj4_JA2emhE_O7yX58v7d1-sbevvpw8frt7fUCtZmioMYVO1kp6yStu1czzunUAx9I4vSMc45mt6wHlsjeN_UrZPMOIsNKFZfkhen1P3aGFPWs08Wp9IIwyHpthGNlKwc7L-kUMAFh5XkJ9LGkFJEp_fRzyYeNQO9zqF3ep1Dr3NokLqkF9Ozc_yhn3H4Y_l9_wI8PwMmWTO5aBbr01-uBtWpVhTu6sRhOdqdx6iT9bhYHHxEm_UQ_L96_AKzBKk1</recordid><startdate>20100815</startdate><enddate>20100815</enddate><creator>Thanigaimalai, Pillaiyar</creator><creator>Sharma, Vinay K.</creator><creator>Lee, Ki-Cheul</creator><creator>Yun, Cheong-Yong</creator><creator>Kim, Youngsoo</creator><creator>Jung, Sang-Hun</creator><general>Elsevier Ltd</general><general>Elsevier</general><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>7QO</scope><scope>8FD</scope><scope>FR3</scope><scope>P64</scope></search><sort><creationdate>20100815</creationdate><title>Refinement of the pharmacophore of 3,4-dihydroquinazoline-2(1 H)-thiones for their anti-melanogenesis activity</title><author>Thanigaimalai, Pillaiyar ; Sharma, Vinay K. ; Lee, Ki-Cheul ; Yun, Cheong-Yong ; Kim, Youngsoo ; Jung, Sang-Hun</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c417t-ed4d93f689c96c78fb28f9e4db56c9681222eaba1be7a42b537f61afce50913</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2010</creationdate><topic>3,4-Quinazoline-2(1 H)-thiones</topic><topic>alpha-MSH - antagonists & inhibitors</topic><topic>alpha-MSH - metabolism</topic><topic>Animals</topic><topic>Biological and medical sciences</topic><topic>Cell Line, Tumor</topic><topic>Inhibitors</topic><topic>Medical sciences</topic><topic>Melanins - biosynthesis</topic><topic>Melanogenesis</topic><topic>Mice</topic><topic>Pharmacology. Drug treatments</topic><topic>Skin, nail, hair, dermoskeleton</topic><topic>Structure-Activity Relationship</topic><topic>Thiones - chemical synthesis</topic><topic>Thiones - chemistry</topic><topic>Thiones - therapeutic use</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Thanigaimalai, Pillaiyar</creatorcontrib><creatorcontrib>Sharma, Vinay K.</creatorcontrib><creatorcontrib>Lee, Ki-Cheul</creatorcontrib><creatorcontrib>Yun, Cheong-Yong</creatorcontrib><creatorcontrib>Kim, Youngsoo</creatorcontrib><creatorcontrib>Jung, Sang-Hun</creatorcontrib><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>Biotechnology Research Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Bioorganic & medicinal chemistry letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Thanigaimalai, Pillaiyar</au><au>Sharma, Vinay K.</au><au>Lee, Ki-Cheul</au><au>Yun, Cheong-Yong</au><au>Kim, Youngsoo</au><au>Jung, Sang-Hun</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Refinement of the pharmacophore of 3,4-dihydroquinazoline-2(1 H)-thiones for their anti-melanogenesis activity</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2010-08-15</date><risdate>2010</risdate><volume>20</volume><issue>16</issue><spage>4771</spage><epage>4773</epage><pages>4771-4773</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>In order to define the structural requirements of quinazoline-2(1
H)-thiones
1 for their inhibitory activity on melanogenesis, a novel series of 3,4-dihydroquinazoline-2(1
H)-thiones (
3a–
h) were prepared and screened for their melanogenesis inhibition on melanoma B16 cell line under the stimulant of α-MSH. The anti-melanogenesis activity of
3 is mainly mediated by the hydrogen bonding ability of thioamide unit in addition to complexation ability of thione and the hydrophobic binding power of side chain substitutions at 3-position. Thus, the pharmacophore of 3,4-dihydroquinazoline-2(1
H)-thiones for their anti-melanogenesis activity could be refined as 3-hydrophobic substituted quinazolinethione.</abstract><cop>Amsterdam</cop><pub>Elsevier Ltd</pub><pmid>20638280</pmid><doi>10.1016/j.bmcl.2010.06.123</doi><tpages>3</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0960-894X |
| ispartof | Bioorganic & medicinal chemistry letters, 2010-08, Vol.20 (16), p.4771-4773 |
| issn | 0960-894X 1464-3405 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_754566112 |
| source | MEDLINE; ScienceDirect Journals (5 years ago - present) |
| subjects | 3,4-Quinazoline-2(1 H)-thiones alpha-MSH - antagonists & inhibitors alpha-MSH - metabolism Animals Biological and medical sciences Cell Line, Tumor Inhibitors Medical sciences Melanins - biosynthesis Melanogenesis Mice Pharmacology. Drug treatments Skin, nail, hair, dermoskeleton Structure-Activity Relationship Thiones - chemical synthesis Thiones - chemistry Thiones - therapeutic use |
| title | Refinement of the pharmacophore of 3,4-dihydroquinazoline-2(1 H)-thiones for their anti-melanogenesis activity |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-02T20%3A28%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=Refinement%20of%20the%20pharmacophore%20of%203,4-dihydroquinazoline-2(1%20H)-thiones%20for%20their%20anti-melanogenesis%20activity&rft.jtitle=Bioorganic%20&%20medicinal%20chemistry%20letters&rft.au=Thanigaimalai,%20Pillaiyar&rft.date=2010-08-15&rft.volume=20&rft.issue=16&rft.spage=4771&rft.epage=4773&rft.pages=4771-4773&rft.issn=0960-894X&rft.eissn=1464-3405&rft_id=info:doi/10.1016/j.bmcl.2010.06.123&rft_dat=%3Cproquest_cross%3E749024202%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=749024202&rft_id=info:pmid/20638280&rft_els_id=S0960894X10009108&rfr_iscdi=true |