A Practical Regioselective Synthesis of Alkylthio- or Arylthioindoles without the Use of Smelly Compounds Such as Thiols
A convenient method for the synthesis of 3-methylthioindoles has been established which does not use smelly compounds such as thiol derivatives. The method, which introduces an alkyl- or arylthio-group into the C3-position of the indole skeleton, was extended to the direct introduction of a methylth...
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Veröffentlicht in: | Chemical & pharmaceutical bulletin 2013/03/01, Vol.61(3), pp.292-303 |
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creator | Hamashima, Toshihiko Mori, Yoshiaki Sawada, Kazunori Kasahara, Yuko Murayama, Daisuke Kamei, Yuto Okuno, Hiroaki Yokoyama, Yuusaku Suzuki, Hideharu |
description | A convenient method for the synthesis of 3-methylthioindoles has been established which does not use smelly compounds such as thiol derivatives. The method, which introduces an alkyl- or arylthio-group into the C3-position of the indole skeleton, was extended to the direct introduction of a methylthio or bromo group at the C2-position using 3-methylthioindoles. No dimerization occurred, and the reaction mechanism was confirmed. The products have the partial structure of potent anti-methicillin-resistant Staphylococcus aureus (anti-MRSA) bromomethylthioindoles (MC 5-8) isolated from marine algae. Furthermore, this reaction could be applied to the synthesis of 3,3-diindolyl thioether which is a core structure of Echinosulfone A. |
doi_str_mv | 10.1248/cpb.c12-00882 |
format | Article |
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The method, which introduces an alkyl- or arylthio-group into the C3-position of the indole skeleton, was extended to the direct introduction of a methylthio or bromo group at the C2-position using 3-methylthioindoles. No dimerization occurred, and the reaction mechanism was confirmed. The products have the partial structure of potent anti-methicillin-resistant Staphylococcus aureus (anti-MRSA) bromomethylthioindoles (MC 5-8) isolated from marine algae. Furthermore, this reaction could be applied to the synthesis of 3,3-diindolyl thioether which is a core structure of Echinosulfone A.</description><identifier>ISSN: 0009-2363</identifier><identifier>EISSN: 1347-5223</identifier><identifier>DOI: 10.1248/cpb.c12-00882</identifier><identifier>PMID: 23221649</identifier><language>eng</language><publisher>Japan: The Pharmaceutical Society of Japan</publisher><subject>Anti-Bacterial Agents - chemical synthesis ; Anti-Bacterial Agents - chemistry ; Anti-Bacterial Agents - pharmacology ; Dimerization ; electrophilic aromatic substitution ; indole ; Indoles - chemistry ; Methicillin-Resistant Staphylococcus aureus - drug effects ; Sulfhydryl Compounds - chemistry ; sulfoxide ; thioether ; trifluoroacetic anhydride</subject><ispartof>Chemical and Pharmaceutical Bulletin, 2013/03/01, Vol.61(3), pp.292-303</ispartof><rights>2013 The Pharmaceutical Society of Japan</rights><rights>Copyright Japan Science and Technology Agency 2013</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c486t-38cf0fc9d9307d1157398d6f87bb376cbc0bb42ac2684c096bec08f9da995db83</citedby><cites>FETCH-LOGICAL-c486t-38cf0fc9d9307d1157398d6f87bb376cbc0bb42ac2684c096bec08f9da995db83</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>315,781,785,1884,27926,27927</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/23221649$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Hamashima, Toshihiko</creatorcontrib><creatorcontrib>Mori, Yoshiaki</creatorcontrib><creatorcontrib>Sawada, Kazunori</creatorcontrib><creatorcontrib>Kasahara, Yuko</creatorcontrib><creatorcontrib>Murayama, Daisuke</creatorcontrib><creatorcontrib>Kamei, Yuto</creatorcontrib><creatorcontrib>Okuno, Hiroaki</creatorcontrib><creatorcontrib>Yokoyama, Yuusaku</creatorcontrib><creatorcontrib>Suzuki, Hideharu</creatorcontrib><title>A Practical Regioselective Synthesis of Alkylthio- or Arylthioindoles without the Use of Smelly Compounds Such as Thiols</title><title>Chemical & pharmaceutical bulletin</title><addtitle>Chem. Pharm. Bull.</addtitle><description>A convenient method for the synthesis of 3-methylthioindoles has been established which does not use smelly compounds such as thiol derivatives. The method, which introduces an alkyl- or arylthio-group into the C3-position of the indole skeleton, was extended to the direct introduction of a methylthio or bromo group at the C2-position using 3-methylthioindoles. No dimerization occurred, and the reaction mechanism was confirmed. The products have the partial structure of potent anti-methicillin-resistant Staphylococcus aureus (anti-MRSA) bromomethylthioindoles (MC 5-8) isolated from marine algae. Furthermore, this reaction could be applied to the synthesis of 3,3-diindolyl thioether which is a core structure of Echinosulfone A.</description><subject>Anti-Bacterial Agents - chemical synthesis</subject><subject>Anti-Bacterial Agents - chemistry</subject><subject>Anti-Bacterial Agents - pharmacology</subject><subject>Dimerization</subject><subject>electrophilic aromatic substitution</subject><subject>indole</subject><subject>Indoles - chemistry</subject><subject>Methicillin-Resistant Staphylococcus aureus - drug effects</subject><subject>Sulfhydryl Compounds - chemistry</subject><subject>sulfoxide</subject><subject>thioether</subject><subject>trifluoroacetic anhydride</subject><issn>0009-2363</issn><issn>1347-5223</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpdkU1P3DAQhq2qqCy0R66VpV64hI4_NrGPqxW0SEhULJwt23FItk682Enb_ff1srBIXGY08jOvRn4QOiNwQSgX3-3GXFhCCwAh6Ac0I4xXxZxS9hHNAEAWlJXsGJ2ktAagc6jYJ3RMGaWk5HKG_i3wr6jt2Fnt8Z177EJy3uX5j8Or7TC2LnUJhwYv_O-tH9suFDhEvIj7oRvq4F3Cf7uxDdOIM48fktstrHrn_RYvQ78J01AnvJpsi3XC93nPp8_oqNE-uS8v_RQ9XF3eL38WN7c_rpeLm8JyUY4FE7aBxspaMqhqQuYVk6IuG1EZw6rSGgvGcKotLQW3IEvjLIhG1lrKeW0EO0Xn-9xNDE-TS6Pqu2TzaXpwYUqKMMIZq_LvZfTbO3Qdpjjk6xThlQDGgcpMFXvKxpBSdI3axK7XcasIqJ0SlZWorEQ9K8n815fUyfSuPtCvDjKw3APrNOpHdwB0zFa8e44riWK7coh9e211VG5g_wFrr6Aw</recordid><startdate>20130301</startdate><enddate>20130301</enddate><creator>Hamashima, Toshihiko</creator><creator>Mori, Yoshiaki</creator><creator>Sawada, Kazunori</creator><creator>Kasahara, Yuko</creator><creator>Murayama, Daisuke</creator><creator>Kamei, Yuto</creator><creator>Okuno, Hiroaki</creator><creator>Yokoyama, Yuusaku</creator><creator>Suzuki, Hideharu</creator><general>The Pharmaceutical Society of Japan</general><general>Japan Science and Technology Agency</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>7TK</scope><scope>7TM</scope><scope>7U9</scope><scope>H94</scope><scope>7X8</scope></search><sort><creationdate>20130301</creationdate><title>A Practical Regioselective Synthesis of Alkylthio- or Arylthioindoles without the Use of Smelly Compounds Such as Thiols</title><author>Hamashima, Toshihiko ; Mori, Yoshiaki ; Sawada, Kazunori ; Kasahara, Yuko ; Murayama, Daisuke ; Kamei, Yuto ; Okuno, Hiroaki ; Yokoyama, Yuusaku ; Suzuki, Hideharu</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c486t-38cf0fc9d9307d1157398d6f87bb376cbc0bb42ac2684c096bec08f9da995db83</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>Anti-Bacterial Agents - chemical synthesis</topic><topic>Anti-Bacterial Agents - chemistry</topic><topic>Anti-Bacterial Agents - pharmacology</topic><topic>Dimerization</topic><topic>electrophilic aromatic substitution</topic><topic>indole</topic><topic>Indoles - chemistry</topic><topic>Methicillin-Resistant Staphylococcus aureus - drug effects</topic><topic>Sulfhydryl Compounds - chemistry</topic><topic>sulfoxide</topic><topic>thioether</topic><topic>trifluoroacetic anhydride</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Hamashima, Toshihiko</creatorcontrib><creatorcontrib>Mori, Yoshiaki</creatorcontrib><creatorcontrib>Sawada, Kazunori</creatorcontrib><creatorcontrib>Kasahara, Yuko</creatorcontrib><creatorcontrib>Murayama, Daisuke</creatorcontrib><creatorcontrib>Kamei, Yuto</creatorcontrib><creatorcontrib>Okuno, Hiroaki</creatorcontrib><creatorcontrib>Yokoyama, Yuusaku</creatorcontrib><creatorcontrib>Suzuki, Hideharu</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Neurosciences Abstracts</collection><collection>Nucleic Acids Abstracts</collection><collection>Virology and AIDS Abstracts</collection><collection>AIDS and Cancer Research Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Chemical & pharmaceutical bulletin</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Hamashima, Toshihiko</au><au>Mori, Yoshiaki</au><au>Sawada, Kazunori</au><au>Kasahara, Yuko</au><au>Murayama, Daisuke</au><au>Kamei, Yuto</au><au>Okuno, Hiroaki</au><au>Yokoyama, Yuusaku</au><au>Suzuki, Hideharu</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A Practical Regioselective Synthesis of Alkylthio- or Arylthioindoles without the Use of Smelly Compounds Such as Thiols</atitle><jtitle>Chemical & pharmaceutical bulletin</jtitle><addtitle>Chem. Pharm. Bull.</addtitle><date>2013-03-01</date><risdate>2013</risdate><volume>61</volume><issue>3</issue><spage>292</spage><epage>303</epage><pages>292-303</pages><issn>0009-2363</issn><eissn>1347-5223</eissn><abstract>A convenient method for the synthesis of 3-methylthioindoles has been established which does not use smelly compounds such as thiol derivatives. The method, which introduces an alkyl- or arylthio-group into the C3-position of the indole skeleton, was extended to the direct introduction of a methylthio or bromo group at the C2-position using 3-methylthioindoles. No dimerization occurred, and the reaction mechanism was confirmed. The products have the partial structure of potent anti-methicillin-resistant Staphylococcus aureus (anti-MRSA) bromomethylthioindoles (MC 5-8) isolated from marine algae. 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subjects | Anti-Bacterial Agents - chemical synthesis Anti-Bacterial Agents - chemistry Anti-Bacterial Agents - pharmacology Dimerization electrophilic aromatic substitution indole Indoles - chemistry Methicillin-Resistant Staphylococcus aureus - drug effects Sulfhydryl Compounds - chemistry sulfoxide thioether trifluoroacetic anhydride |
title | A Practical Regioselective Synthesis of Alkylthio- or Arylthioindoles without the Use of Smelly Compounds Such as Thiols |
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