Identification of Indoline-2-thione Analogs as Novel Potent Inhibitors of α-Melanocyte Stimulating Hormone Induced Melanogenesis
Based on the hits, 3,4-dihydroquinazoline-2-thione (1) and benzimidazole-2-thione (2), a series of indole-2-thione (3) and indole-2-thiol inhibitors (4) of melanogenesis were designed, synthesized and evaluated in melanoma B16 cells under the stimulant of α-melanocyte stimulating hormone (α-MSH). Th...
Gespeichert in:
| Veröffentlicht in: | Chemical & pharmaceutical bulletin 2011/10/01, Vol.59(10), pp.1285-1288 |
|---|---|
| Hauptverfasser: | , , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 1288 |
|---|---|
| container_issue | 10 |
| container_start_page | 1285 |
| container_title | Chemical & pharmaceutical bulletin |
| container_volume | 59 |
| creator | Thanigaimalai, Pillaiyar Lee, Ki-Cheul Sharma, Vinay Kumar Sharma, Niti Roh, Eunmiri Kim, Youngsoo Jung, Sang-Hun |
| description | Based on the hits, 3,4-dihydroquinazoline-2-thione (1) and benzimidazole-2-thione (2), a series of indole-2-thione (3) and indole-2-thiol inhibitors (4) of melanogenesis were designed, synthesized and evaluated in melanoma B16 cells under the stimulant of α-melanocyte stimulating hormone (α-MSH). The indole-2-thione compounds (3a—g) exhibited an effective inhibitory activity on melanin synthesis. The Structure–Activity Relationship (SAR) studies of 2 have revealed that in potent inhibitor 3a (>100% inhibition at 30 μM, IC50=1.40 μM) the role of nitrogen (3-N) at 3-position is insignificance. In addition, the hydrophobic substituents of 3 were better than the hydrophilic one. However, conversion of thione (–C=S, 3) to thiol (–C–SH, 4) led to decrease in the potency. |
| doi_str_mv | 10.1248/cpb.59.1285 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_896240195</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>896240195</sourcerecordid><originalsourceid>FETCH-LOGICAL-c575t-be67560ce1c7e0c16ab30f15aa3a2af48f08ae4c27ed86db6cc3f90d4b3bb5253</originalsourceid><addsrcrecordid>eNpFkMtu1DAUhi1ERaeFFXvkHQuU1pfYSZalKu1I5SIBa8t2TmZcJfZgO5W65JF4kT4TjmYYNrZ1zvd_sn6E3lJyQVndXtqduRBdebfiBVpRXjeVYIy_RCtCSFcxLvkpOkvpgRAmSMNfoVNGO8llTVbo97oHn93grM4ueBwGvPZ9GJ2HilV5W2aAr7wewyZhnfCX8Agj_hZySRVy64zLIaYl9_yn-gyj9sE-ZcDfs5vmsUj9Bt-FOC2eYp4t9HiPbcBDcuk1Ohn0mODN4T5HPz_d_Li-q-6_3q6vr-4rKxqRKwOyEZJYoLYBYqnUhpOBCq25Znqo24G0GmrLGuhb2RtpLR860teGGyOY4Ofo_d67i-HXDCmrySULY_kKhDmptpOsJrRbyA970saQUoRB7aKbdHxSlKilclUqV6JTS-WFfnfwzmaC_sj-67gAH_fAQ8p6A0dAx-zsCEcZOZyL9f9yq6MCz_8C7XKXkA</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>896240195</pqid></control><display><type>article</type><title>Identification of Indoline-2-thione Analogs as Novel Potent Inhibitors of α-Melanocyte Stimulating Hormone Induced Melanogenesis</title><source>MEDLINE</source><source>J-STAGE (Japan Science & Technology Information Aggregator, Electronic) Freely Available Titles - Japanese</source><source>EZB-FREE-00999 freely available EZB journals</source><source>Free Full-Text Journals in Chemistry</source><creator>Thanigaimalai, Pillaiyar ; Lee, Ki-Cheul ; Sharma, Vinay Kumar ; Sharma, Niti ; Roh, Eunmiri ; Kim, Youngsoo ; Jung, Sang-Hun</creator><creatorcontrib>Thanigaimalai, Pillaiyar ; Lee, Ki-Cheul ; Sharma, Vinay Kumar ; Sharma, Niti ; Roh, Eunmiri ; Kim, Youngsoo ; Jung, Sang-Hun</creatorcontrib><description>Based on the hits, 3,4-dihydroquinazoline-2-thione (1) and benzimidazole-2-thione (2), a series of indole-2-thione (3) and indole-2-thiol inhibitors (4) of melanogenesis were designed, synthesized and evaluated in melanoma B16 cells under the stimulant of α-melanocyte stimulating hormone (α-MSH). The indole-2-thione compounds (3a—g) exhibited an effective inhibitory activity on melanin synthesis. The Structure–Activity Relationship (SAR) studies of 2 have revealed that in potent inhibitor 3a (>100% inhibition at 30 μM, IC50=1.40 μM) the role of nitrogen (3-N) at 3-position is insignificance. In addition, the hydrophobic substituents of 3 were better than the hydrophilic one. However, conversion of thione (–C=S, 3) to thiol (–C–SH, 4) led to decrease in the potency.</description><identifier>ISSN: 0009-2363</identifier><identifier>EISSN: 1347-5223</identifier><identifier>DOI: 10.1248/cpb.59.1285</identifier><identifier>PMID: 21963640</identifier><language>eng</language><publisher>Japan: The Pharmaceutical Society of Japan</publisher><subject>alpha-MSH - antagonists & inhibitors ; Animals ; benzimidazole-2-thione ; Cell Line, Tumor ; Drug Design ; Drug Discovery ; Drug Evaluation, Preclinical ; Humans ; indole-2-thiol ; Indoles - chemistry ; Inhibitory Concentration 50 ; inoline-2-thione ; Melanins - physiology ; melanogenesis inhibitor ; Melanoma, Experimental - metabolism ; Molecular Targeted Therapy ; Structure-Activity Relationship ; Thiones - chemistry</subject><ispartof>Chemical and Pharmaceutical Bulletin, 2011/10/01, Vol.59(10), pp.1285-1288</ispartof><rights>2011 The Pharmaceutical Society of Japan</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c575t-be67560ce1c7e0c16ab30f15aa3a2af48f08ae4c27ed86db6cc3f90d4b3bb5253</citedby><cites>FETCH-LOGICAL-c575t-be67560ce1c7e0c16ab30f15aa3a2af48f08ae4c27ed86db6cc3f90d4b3bb5253</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,1876,4009,27902,27903,27904</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/21963640$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Thanigaimalai, Pillaiyar</creatorcontrib><creatorcontrib>Lee, Ki-Cheul</creatorcontrib><creatorcontrib>Sharma, Vinay Kumar</creatorcontrib><creatorcontrib>Sharma, Niti</creatorcontrib><creatorcontrib>Roh, Eunmiri</creatorcontrib><creatorcontrib>Kim, Youngsoo</creatorcontrib><creatorcontrib>Jung, Sang-Hun</creatorcontrib><title>Identification of Indoline-2-thione Analogs as Novel Potent Inhibitors of α-Melanocyte Stimulating Hormone Induced Melanogenesis</title><title>Chemical & pharmaceutical bulletin</title><addtitle>Chem. Pharm. Bull.</addtitle><description>Based on the hits, 3,4-dihydroquinazoline-2-thione (1) and benzimidazole-2-thione (2), a series of indole-2-thione (3) and indole-2-thiol inhibitors (4) of melanogenesis were designed, synthesized and evaluated in melanoma B16 cells under the stimulant of α-melanocyte stimulating hormone (α-MSH). The indole-2-thione compounds (3a—g) exhibited an effective inhibitory activity on melanin synthesis. The Structure–Activity Relationship (SAR) studies of 2 have revealed that in potent inhibitor 3a (>100% inhibition at 30 μM, IC50=1.40 μM) the role of nitrogen (3-N) at 3-position is insignificance. In addition, the hydrophobic substituents of 3 were better than the hydrophilic one. However, conversion of thione (–C=S, 3) to thiol (–C–SH, 4) led to decrease in the potency.</description><subject>alpha-MSH - antagonists & inhibitors</subject><subject>Animals</subject><subject>benzimidazole-2-thione</subject><subject>Cell Line, Tumor</subject><subject>Drug Design</subject><subject>Drug Discovery</subject><subject>Drug Evaluation, Preclinical</subject><subject>Humans</subject><subject>indole-2-thiol</subject><subject>Indoles - chemistry</subject><subject>Inhibitory Concentration 50</subject><subject>inoline-2-thione</subject><subject>Melanins - physiology</subject><subject>melanogenesis inhibitor</subject><subject>Melanoma, Experimental - metabolism</subject><subject>Molecular Targeted Therapy</subject><subject>Structure-Activity Relationship</subject><subject>Thiones - chemistry</subject><issn>0009-2363</issn><issn>1347-5223</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpFkMtu1DAUhi1ERaeFFXvkHQuU1pfYSZalKu1I5SIBa8t2TmZcJfZgO5W65JF4kT4TjmYYNrZ1zvd_sn6E3lJyQVndXtqduRBdebfiBVpRXjeVYIy_RCtCSFcxLvkpOkvpgRAmSMNfoVNGO8llTVbo97oHn93grM4ueBwGvPZ9GJ2HilV5W2aAr7wewyZhnfCX8Agj_hZySRVy64zLIaYl9_yn-gyj9sE-ZcDfs5vmsUj9Bt-FOC2eYp4t9HiPbcBDcuk1Ohn0mODN4T5HPz_d_Li-q-6_3q6vr-4rKxqRKwOyEZJYoLYBYqnUhpOBCq25Znqo24G0GmrLGuhb2RtpLR860teGGyOY4Ofo_d67i-HXDCmrySULY_kKhDmptpOsJrRbyA970saQUoRB7aKbdHxSlKilclUqV6JTS-WFfnfwzmaC_sj-67gAH_fAQ8p6A0dAx-zsCEcZOZyL9f9yq6MCz_8C7XKXkA</recordid><startdate>2011</startdate><enddate>2011</enddate><creator>Thanigaimalai, Pillaiyar</creator><creator>Lee, Ki-Cheul</creator><creator>Sharma, Vinay Kumar</creator><creator>Sharma, Niti</creator><creator>Roh, Eunmiri</creator><creator>Kim, Youngsoo</creator><creator>Jung, Sang-Hun</creator><general>The Pharmaceutical Society of Japan</general><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></search><sort><creationdate>2011</creationdate><title>Identification of Indoline-2-thione Analogs as Novel Potent Inhibitors of α-Melanocyte Stimulating Hormone Induced Melanogenesis</title><author>Thanigaimalai, Pillaiyar ; Lee, Ki-Cheul ; Sharma, Vinay Kumar ; Sharma, Niti ; Roh, Eunmiri ; Kim, Youngsoo ; Jung, Sang-Hun</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c575t-be67560ce1c7e0c16ab30f15aa3a2af48f08ae4c27ed86db6cc3f90d4b3bb5253</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>alpha-MSH - antagonists & inhibitors</topic><topic>Animals</topic><topic>benzimidazole-2-thione</topic><topic>Cell Line, Tumor</topic><topic>Drug Design</topic><topic>Drug Discovery</topic><topic>Drug Evaluation, Preclinical</topic><topic>Humans</topic><topic>indole-2-thiol</topic><topic>Indoles - chemistry</topic><topic>Inhibitory Concentration 50</topic><topic>inoline-2-thione</topic><topic>Melanins - physiology</topic><topic>melanogenesis inhibitor</topic><topic>Melanoma, Experimental - metabolism</topic><topic>Molecular Targeted Therapy</topic><topic>Structure-Activity Relationship</topic><topic>Thiones - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Thanigaimalai, Pillaiyar</creatorcontrib><creatorcontrib>Lee, Ki-Cheul</creatorcontrib><creatorcontrib>Sharma, Vinay Kumar</creatorcontrib><creatorcontrib>Sharma, Niti</creatorcontrib><creatorcontrib>Roh, Eunmiri</creatorcontrib><creatorcontrib>Kim, Youngsoo</creatorcontrib><creatorcontrib>Jung, Sang-Hun</creatorcontrib><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><jtitle>Chemical & pharmaceutical bulletin</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Thanigaimalai, Pillaiyar</au><au>Lee, Ki-Cheul</au><au>Sharma, Vinay Kumar</au><au>Sharma, Niti</au><au>Roh, Eunmiri</au><au>Kim, Youngsoo</au><au>Jung, Sang-Hun</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Identification of Indoline-2-thione Analogs as Novel Potent Inhibitors of α-Melanocyte Stimulating Hormone Induced Melanogenesis</atitle><jtitle>Chemical & pharmaceutical bulletin</jtitle><addtitle>Chem. Pharm. Bull.</addtitle><date>2011</date><risdate>2011</risdate><volume>59</volume><issue>10</issue><spage>1285</spage><epage>1288</epage><pages>1285-1288</pages><issn>0009-2363</issn><eissn>1347-5223</eissn><abstract>Based on the hits, 3,4-dihydroquinazoline-2-thione (1) and benzimidazole-2-thione (2), a series of indole-2-thione (3) and indole-2-thiol inhibitors (4) of melanogenesis were designed, synthesized and evaluated in melanoma B16 cells under the stimulant of α-melanocyte stimulating hormone (α-MSH). The indole-2-thione compounds (3a—g) exhibited an effective inhibitory activity on melanin synthesis. The Structure–Activity Relationship (SAR) studies of 2 have revealed that in potent inhibitor 3a (>100% inhibition at 30 μM, IC50=1.40 μM) the role of nitrogen (3-N) at 3-position is insignificance. In addition, the hydrophobic substituents of 3 were better than the hydrophilic one. However, conversion of thione (–C=S, 3) to thiol (–C–SH, 4) led to decrease in the potency.</abstract><cop>Japan</cop><pub>The Pharmaceutical Society of Japan</pub><pmid>21963640</pmid><doi>10.1248/cpb.59.1285</doi><tpages>4</tpages><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0009-2363 |
| ispartof | Chemical and Pharmaceutical Bulletin, 2011/10/01, Vol.59(10), pp.1285-1288 |
| issn | 0009-2363 1347-5223 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_896240195 |
| source | MEDLINE; J-STAGE (Japan Science & Technology Information Aggregator, Electronic) Freely Available Titles - Japanese; EZB-FREE-00999 freely available EZB journals; Free Full-Text Journals in Chemistry |
| subjects | alpha-MSH - antagonists & inhibitors Animals benzimidazole-2-thione Cell Line, Tumor Drug Design Drug Discovery Drug Evaluation, Preclinical Humans indole-2-thiol Indoles - chemistry Inhibitory Concentration 50 inoline-2-thione Melanins - physiology melanogenesis inhibitor Melanoma, Experimental - metabolism Molecular Targeted Therapy Structure-Activity Relationship Thiones - chemistry |
| title | Identification of Indoline-2-thione Analogs as Novel Potent Inhibitors of α-Melanocyte Stimulating Hormone Induced Melanogenesis |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-24T03%3A23%3A15IST&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=Identification%20of%20Indoline-2-thione%20Analogs%20as%20Novel%20Potent%20Inhibitors%20of%20%CE%B1-Melanocyte%20Stimulating%20Hormone%20Induced%20Melanogenesis&rft.jtitle=Chemical%20&%20pharmaceutical%20bulletin&rft.au=Thanigaimalai,%20Pillaiyar&rft.date=2011&rft.volume=59&rft.issue=10&rft.spage=1285&rft.epage=1288&rft.pages=1285-1288&rft.issn=0009-2363&rft.eissn=1347-5223&rft_id=info:doi/10.1248/cpb.59.1285&rft_dat=%3Cproquest_cross%3E896240195%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=896240195&rft_id=info:pmid/21963640&rfr_iscdi=true |