Synthesis and antifungal activity of alkylthio and alkylsulfonyl derivatives of SM-8668
Triazole analogues which contained alkylthio or alkylsulfonyl groups where synthesized as derivatives of antifungal SM-8668 and estimated for their in vitro and in vivo activity. Derivatives having pentylthio, heptylthio or nonylthio groups showed excellent efficacy against both candidiasis and aspe...
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Veröffentlicht in: | Bioorganic & medicinal chemistry 1996-02, Vol.4 (2), p.263-273 |
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container_title | Bioorganic & medicinal chemistry |
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creator | Miyauchi, Hiroshi Kozuki, Koichi Tanio, Tomoharu Ohashi, Naohito |
description | Triazole analogues which contained alkylthio or alkylsulfonyl groups where synthesized as derivatives of antifungal SM-8668 and estimated for their in vitro and in vivo activity. Derivatives having pentylthio, heptylthio or nonylthio groups showed excellent efficacy against both candidiasis and aspergillosis. Introduction of a hydrophilic group at the end of their alkyl chain made their activity stronger. Especially, 5-hydroxypentylthio and 7-hydroxyheptylthio derivatives showed the strongest antifungal activity.
Alkyl derivatives of sulfur-containing triazoles
1 were synthesized and estimated for their antifungal activities. Some of the compounds showed potent activities against both candidiasis and aspergillosis. The induction of hydroxyl group at the end of their alkyl chain made their activities stronger. |
doi_str_mv | 10.1016/0968-0896(95)00180-8 |
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Alkyl derivatives of sulfur-containing triazoles
1 were synthesized and estimated for their antifungal activities. Some of the compounds showed potent activities against both candidiasis and aspergillosis. The induction of hydroxyl group at the end of their alkyl chain made their activities stronger.</description><identifier>ISSN: 0968-0896</identifier><identifier>EISSN: 1464-3391</identifier><identifier>DOI: 10.1016/0968-0896(95)00180-8</identifier><identifier>PMID: 8814884</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>Alkylation ; Animals ; Antifungal Agents - chemical synthesis ; Antifungal Agents - chemistry ; Antifungal Agents - pharmacology ; Antifungal Agents - therapeutic use ; Aspergillosis - drug therapy ; Candidiasis - drug therapy ; Disease Models, Animal ; Magnetic Resonance Spectroscopy ; Male ; Mice ; Structure-Activity Relationship ; Sulfur - chemistry ; Triazoles - chemistry ; Triazoles - metabolism</subject><ispartof>Bioorganic & medicinal chemistry, 1996-02, Vol.4 (2), p.263-273</ispartof><rights>1996</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c357t-9236f83759456943d48b6f93715fb48f89c248fdeb6f61f100350afe8f98ae983</citedby><cites>FETCH-LOGICAL-c357t-9236f83759456943d48b6f93715fb48f89c248fdeb6f61f100350afe8f98ae983</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/0968089695001808$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3536,27903,27904,65309</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/8814884$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Miyauchi, Hiroshi</creatorcontrib><creatorcontrib>Kozuki, Koichi</creatorcontrib><creatorcontrib>Tanio, Tomoharu</creatorcontrib><creatorcontrib>Ohashi, Naohito</creatorcontrib><title>Synthesis and antifungal activity of alkylthio and alkylsulfonyl derivatives of SM-8668</title><title>Bioorganic & medicinal chemistry</title><addtitle>Bioorg Med Chem</addtitle><description>Triazole analogues which contained alkylthio or alkylsulfonyl groups where synthesized as derivatives of antifungal SM-8668 and estimated for their in vitro and in vivo activity. Derivatives having pentylthio, heptylthio or nonylthio groups showed excellent efficacy against both candidiasis and aspergillosis. Introduction of a hydrophilic group at the end of their alkyl chain made their activity stronger. Especially, 5-hydroxypentylthio and 7-hydroxyheptylthio derivatives showed the strongest antifungal activity.
Alkyl derivatives of sulfur-containing triazoles
1 were synthesized and estimated for their antifungal activities. Some of the compounds showed potent activities against both candidiasis and aspergillosis. The induction of hydroxyl group at the end of their alkyl chain made their activities stronger.</description><subject>Alkylation</subject><subject>Animals</subject><subject>Antifungal Agents - chemical synthesis</subject><subject>Antifungal Agents - chemistry</subject><subject>Antifungal Agents - pharmacology</subject><subject>Antifungal Agents - therapeutic use</subject><subject>Aspergillosis - drug therapy</subject><subject>Candidiasis - drug therapy</subject><subject>Disease Models, Animal</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Male</subject><subject>Mice</subject><subject>Structure-Activity Relationship</subject><subject>Sulfur - chemistry</subject><subject>Triazoles - chemistry</subject><subject>Triazoles - metabolism</subject><issn>0968-0896</issn><issn>1464-3391</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1996</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kE1LxDAQhoMo6_rxDxR6Ej1UkybNTi6CLH7BiodVPIZsO3Gj3XZN2oX-e1u77NFDGDLz5B3yEHLG6DWjTN5QJSGmoOSlSq8oZUBj2CNjJqSIOVdsn4x3yCE5CuGLUpoIxUZkBMAEgBiTj3lb1ksMLkSmzLtTO9uUn6aITFa7javbqLKRKb7bol66aoD6W2gKW5VtEeXo3cZ0LIYenb_EICWckANrioCn23pM3h_u36ZP8ez18Xl6N4sznk7qWCVcWuCTVIlUKsFzAQtpFZ-w1C4EWFBZ0pUcu65kllHKU2osglVgUAE_JhdD7tpXPw2GWq9cyLAoTIlVE_QEGEsSpTpQDGDmqxA8Wr32bmV8qxnVvU_dy9K9LK1S_edT9_nn2_xmscJ892grsJvfDnPsPrlx6HXIHJYZ5s5jVuu8cv8v-AUiHoRO</recordid><startdate>19960201</startdate><enddate>19960201</enddate><creator>Miyauchi, Hiroshi</creator><creator>Kozuki, Koichi</creator><creator>Tanio, Tomoharu</creator><creator>Ohashi, Naohito</creator><general>Elsevier Ltd</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>19960201</creationdate><title>Synthesis and antifungal activity of alkylthio and alkylsulfonyl derivatives of SM-8668</title><author>Miyauchi, Hiroshi ; Kozuki, Koichi ; Tanio, Tomoharu ; Ohashi, Naohito</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c357t-9236f83759456943d48b6f93715fb48f89c248fdeb6f61f100350afe8f98ae983</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1996</creationdate><topic>Alkylation</topic><topic>Animals</topic><topic>Antifungal Agents - chemical synthesis</topic><topic>Antifungal Agents - chemistry</topic><topic>Antifungal Agents - pharmacology</topic><topic>Antifungal Agents - therapeutic use</topic><topic>Aspergillosis - drug therapy</topic><topic>Candidiasis - drug therapy</topic><topic>Disease Models, Animal</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Male</topic><topic>Mice</topic><topic>Structure-Activity Relationship</topic><topic>Sulfur - chemistry</topic><topic>Triazoles - chemistry</topic><topic>Triazoles - metabolism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Miyauchi, Hiroshi</creatorcontrib><creatorcontrib>Kozuki, Koichi</creatorcontrib><creatorcontrib>Tanio, Tomoharu</creatorcontrib><creatorcontrib>Ohashi, Naohito</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>Bioorganic & medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Miyauchi, Hiroshi</au><au>Kozuki, Koichi</au><au>Tanio, Tomoharu</au><au>Ohashi, Naohito</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and antifungal activity of alkylthio and alkylsulfonyl derivatives of SM-8668</atitle><jtitle>Bioorganic & medicinal chemistry</jtitle><addtitle>Bioorg Med Chem</addtitle><date>1996-02-01</date><risdate>1996</risdate><volume>4</volume><issue>2</issue><spage>263</spage><epage>273</epage><pages>263-273</pages><issn>0968-0896</issn><eissn>1464-3391</eissn><abstract>Triazole analogues which contained alkylthio or alkylsulfonyl groups where synthesized as derivatives of antifungal SM-8668 and estimated for their in vitro and in vivo activity. Derivatives having pentylthio, heptylthio or nonylthio groups showed excellent efficacy against both candidiasis and aspergillosis. Introduction of a hydrophilic group at the end of their alkyl chain made their activity stronger. Especially, 5-hydroxypentylthio and 7-hydroxyheptylthio derivatives showed the strongest antifungal activity.
Alkyl derivatives of sulfur-containing triazoles
1 were synthesized and estimated for their antifungal activities. Some of the compounds showed potent activities against both candidiasis and aspergillosis. The induction of hydroxyl group at the end of their alkyl chain made their activities stronger.</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>8814884</pmid><doi>10.1016/0968-0896(95)00180-8</doi><tpages>11</tpages></addata></record> |
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source | MEDLINE; Elsevier ScienceDirect Journals |
subjects | Alkylation Animals Antifungal Agents - chemical synthesis Antifungal Agents - chemistry Antifungal Agents - pharmacology Antifungal Agents - therapeutic use Aspergillosis - drug therapy Candidiasis - drug therapy Disease Models, Animal Magnetic Resonance Spectroscopy Male Mice Structure-Activity Relationship Sulfur - chemistry Triazoles - chemistry Triazoles - metabolism |
title | Synthesis and antifungal activity of alkylthio and alkylsulfonyl derivatives of SM-8668 |
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