Synthesis of novel triazole derivatives as potent inhibitor of allene oxide synthase (CYP74A), a key enzyme in jasmonic acid biosynthesis
A series of new triazole derivatives was synthesized and their inhibitory activity against allene oxide synthase (AOS, CYP74A), a key enzyme in jasmonic acid biosynthesis, was evaluated. Structure-activity relationship studies revealed that methyl 8-[1-(naphthalen-2-yl)-2-(1,2,4-triazol-1-yl)ethoxy]...
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Veröffentlicht in: | Journal of Pesticide Science 2012/03/20, Vol.37(1), pp.80-84 |
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creator | Oh, Keimei Nakai, Kouta Yamada, Kazuhiro Yoshizawa, Yuko |
description | A series of new triazole derivatives was synthesized and their inhibitory activity against allene oxide synthase (AOS, CYP74A), a key enzyme in jasmonic acid biosynthesis, was evaluated. Structure-activity relationship studies revealed that methyl 8-[1-(naphthalen-2-yl)-2-(1,2,4-triazol-1-yl)ethoxy]octanate (4i) and methyl 8-[1-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-yl)ethoxy]octanate (4g) exhibit potent inhibitory activity to allene oxide synthase, with IC50 values of 0.75±0.30 and 0.84±0.60 μM, respectively. |
doi_str_mv | 10.1584/jpestics.D11-006 |
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Pestic. Sci.</addtitle><description>A series of new triazole derivatives was synthesized and their inhibitory activity against allene oxide synthase (AOS, CYP74A), a key enzyme in jasmonic acid biosynthesis, was evaluated. Structure-activity relationship studies revealed that methyl 8-[1-(naphthalen-2-yl)-2-(1,2,4-triazol-1-yl)ethoxy]octanate (4i) and methyl 8-[1-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-yl)ethoxy]octanate (4g) exhibit potent inhibitory activity to allene oxide synthase, with IC50 values of 0.75±0.30 and 0.84±0.60 μM, respectively.</description><subject>allene oxide synthase inhibitor</subject><subject>crop protection</subject><subject>jasmonic acid</subject><issn>1348-589X</issn><issn>1349-0923</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><recordid>eNpFkE1LAzEQhoMoWGrvHnNUcGuy2Y_ssVSrQkFBBT2FbDJrU7ebkoTi9h_4r921tl5m5vA-78CD0DklY5ry5Hq5Bh-M8uMbSiNCsiM0oCwpIlLE7Pj35lHKi7dTNPJ-SQihOcuLIhug7-e2CQvwxmNb4cZuoMbBGbm1NWANzmxkMBvwWHq8tgGagE2zMKUJ1vWErGtoANsvowH7vkt6wBfT96c8mVxeYYk_ocXQbNsVdCReSr-yjVFYKqNxaazf_z9DJ5WsPYz-9hC9zm5fpvfR_PHuYTqZRyqlaYgqlYFkaZHynBMeq4JqLmnGuWJ5zFMNHGQMJWhNoaKq0qyAinGImaZlQhQbIrLrVc5676ASa2dW0rWCEtHbFHuborMpOpsdMtshSx_kBxwA6bpYDf8AywXtxx94CKiFdAIa9gPghIeG</recordid><startdate>20120101</startdate><enddate>20120101</enddate><creator>Oh, Keimei</creator><creator>Nakai, Kouta</creator><creator>Yamada, Kazuhiro</creator><creator>Yoshizawa, Yuko</creator><general>Pesticide Science Society of Japan</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20120101</creationdate><title>Synthesis of novel triazole derivatives as potent inhibitor of allene oxide synthase (CYP74A), a key enzyme in jasmonic acid biosynthesis</title><author>Oh, Keimei ; Nakai, Kouta ; Yamada, Kazuhiro ; Yoshizawa, Yuko</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c515t-fc6ea3595878082c91d8a1688c37285de8ea2ebedd1ef1cfd39ef38e23d1b40c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>allene oxide synthase inhibitor</topic><topic>crop protection</topic><topic>jasmonic acid</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Oh, Keimei</creatorcontrib><creatorcontrib>Nakai, Kouta</creatorcontrib><creatorcontrib>Yamada, Kazuhiro</creatorcontrib><creatorcontrib>Yoshizawa, Yuko</creatorcontrib><collection>CrossRef</collection><jtitle>Journal of Pesticide Science</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Oh, Keimei</au><au>Nakai, Kouta</au><au>Yamada, Kazuhiro</au><au>Yoshizawa, Yuko</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of novel triazole derivatives as potent inhibitor of allene oxide synthase (CYP74A), a key enzyme in jasmonic acid biosynthesis</atitle><jtitle>Journal of Pesticide Science</jtitle><addtitle>J. Pestic. Sci.</addtitle><date>2012-01-01</date><risdate>2012</risdate><volume>37</volume><issue>1</issue><spage>80</spage><epage>84</epage><pages>80-84</pages><issn>1348-589X</issn><eissn>1349-0923</eissn><abstract>A series of new triazole derivatives was synthesized and their inhibitory activity against allene oxide synthase (AOS, CYP74A), a key enzyme in jasmonic acid biosynthesis, was evaluated. Structure-activity relationship studies revealed that methyl 8-[1-(naphthalen-2-yl)-2-(1,2,4-triazol-1-yl)ethoxy]octanate (4i) and methyl 8-[1-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-yl)ethoxy]octanate (4g) exhibit potent inhibitory activity to allene oxide synthase, with IC50 values of 0.75±0.30 and 0.84±0.60 μM, respectively.</abstract><pub>Pesticide Science Society of Japan</pub><doi>10.1584/jpestics.D11-006</doi><tpages>5</tpages><oa>free_for_read</oa></addata></record> |
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source | J-STAGE (Japan Science & Technology Information Aggregator, Electronic) Freely Available Titles - Japanese; Open Access Titles of Japan; AgriKnowledge(アグリナレッジ)AGROLib |
subjects | allene oxide synthase inhibitor crop protection jasmonic acid |
title | Synthesis of novel triazole derivatives as potent inhibitor of allene oxide synthase (CYP74A), a key enzyme in jasmonic acid biosynthesis |
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