Bioisostere of valtrate, anti-HIV principle by inhibition for nuclear export of Rev
Based on the design from the MO calculation, 5,6-dihydrovaltrate ( 2) was synthesized and revealed to be the bioisostere of valtrate ( 1) showing anti-HIV activity by inhibition for nuclear export of Rev. Rational design by the MO calculation disclosed 5,6-dihydrovaltrate ( 2) as the bioisostere of...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2010-04, Vol.20 (7), p.2159-2162 |
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| container_title | Bioorganic & medicinal chemistry letters |
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| creator | Tamura, Satoru Shimizu, Nobuhiro Fujiwara, Katsuaki Kaneko, Masafumi Kimura, Tominori Murakami, Nobutoshi |
| description | Based on the design from the MO calculation, 5,6-dihydrovaltrate (
2) was synthesized and revealed to be the bioisostere of valtrate (
1) showing anti-HIV activity by inhibition for nuclear export of Rev.
Rational design by the MO calculation disclosed 5,6-dihydrovaltrate (
2) as the bioisostere of valtrate (
1), the Rev-export inhibitor with anti-HIV activity. The synthesis of
2 was accomplished by ingenious use of asymmetric Diels–Alder reaction and stereoselective epoxidation associated with the adjacent hydroxyl group. Because of similar biological potency to
1, the analog
2 should be recognized as a promising scaffold for new anti-HIV agents with an unprecedented mechanism of action, inhibition for nuclear export of Rev protein, in the conventional remedy. |
| doi_str_mv | 10.1016/j.bmcl.2010.02.038 |
| format | Article |
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2) was synthesized and revealed to be the bioisostere of valtrate (
1) showing anti-HIV activity by inhibition for nuclear export of Rev.
Rational design by the MO calculation disclosed 5,6-dihydrovaltrate (
2) as the bioisostere of valtrate (
1), the Rev-export inhibitor with anti-HIV activity. The synthesis of
2 was accomplished by ingenious use of asymmetric Diels–Alder reaction and stereoselective epoxidation associated with the adjacent hydroxyl group. Because of similar biological potency to
1, the analog
2 should be recognized as a promising scaffold for new anti-HIV agents with an unprecedented mechanism of action, inhibition for nuclear export of Rev protein, in the conventional remedy.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2010.02.038</identifier><identifier>PMID: 20207540</identifier><language>eng</language><publisher>Amsterdam: Elsevier Ltd</publisher><subject>Active Transport, Cell Nucleus - drug effects ; Anti-HIV ; Anti-HIV Agents - chemistry ; Anti-HIV Agents - pharmacology ; Antibiotics. Antiinfectious agents. Antiparasitic agents ; Antiviral agents ; Bioisostere ; Biological and medical sciences ; Gene Products, rev - metabolism ; HeLa Cells ; HIV Infections - drug therapy ; Human immunodeficiency virus ; Humans ; Iridoid ; Iridoids - chemistry ; Iridoids - pharmacology ; Medical sciences ; Molecular Conformation ; Pharmacology. Drug treatments ; Rev-export inhibitor ; Valtrate</subject><ispartof>Bioorganic & medicinal chemistry letters, 2010-04, Vol.20 (7), p.2159-2162</ispartof><rights>2010 Elsevier Ltd</rights><rights>2015 INIST-CNRS</rights><rights>2010 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c483t-8b823984945b5506cef26f4e6522b3c6edb548c120b603bf66e6c8859fabad553</citedby><cites>FETCH-LOGICAL-c483t-8b823984945b5506cef26f4e6522b3c6edb548c120b603bf66e6c8859fabad553</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.bmcl.2010.02.038$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=22824873$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/20207540$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Tamura, Satoru</creatorcontrib><creatorcontrib>Shimizu, Nobuhiro</creatorcontrib><creatorcontrib>Fujiwara, Katsuaki</creatorcontrib><creatorcontrib>Kaneko, Masafumi</creatorcontrib><creatorcontrib>Kimura, Tominori</creatorcontrib><creatorcontrib>Murakami, Nobutoshi</creatorcontrib><title>Bioisostere of valtrate, anti-HIV principle by inhibition for nuclear export of Rev</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>Based on the design from the MO calculation, 5,6-dihydrovaltrate (
2) was synthesized and revealed to be the bioisostere of valtrate (
1) showing anti-HIV activity by inhibition for nuclear export of Rev.
Rational design by the MO calculation disclosed 5,6-dihydrovaltrate (
2) as the bioisostere of valtrate (
1), the Rev-export inhibitor with anti-HIV activity. The synthesis of
2 was accomplished by ingenious use of asymmetric Diels–Alder reaction and stereoselective epoxidation associated with the adjacent hydroxyl group. Because of similar biological potency to
1, the analog
2 should be recognized as a promising scaffold for new anti-HIV agents with an unprecedented mechanism of action, inhibition for nuclear export of Rev protein, in the conventional remedy.</description><subject>Active Transport, Cell Nucleus - drug effects</subject><subject>Anti-HIV</subject><subject>Anti-HIV Agents - chemistry</subject><subject>Anti-HIV Agents - pharmacology</subject><subject>Antibiotics. Antiinfectious agents. Antiparasitic agents</subject><subject>Antiviral agents</subject><subject>Bioisostere</subject><subject>Biological and medical sciences</subject><subject>Gene Products, rev - metabolism</subject><subject>HeLa Cells</subject><subject>HIV Infections - drug therapy</subject><subject>Human immunodeficiency virus</subject><subject>Humans</subject><subject>Iridoid</subject><subject>Iridoids - chemistry</subject><subject>Iridoids - pharmacology</subject><subject>Medical sciences</subject><subject>Molecular Conformation</subject><subject>Pharmacology. Drug treatments</subject><subject>Rev-export inhibitor</subject><subject>Valtrate</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>eNqFkF1rFDEUhoModtv6B7yQ3Ig3nfVMvjYD3tSitlAoaBXvQpI5wSyzkzXJLvbfO8OuemevDhye9-Wch5CXLSxbaNXb9dJt_LBkMC2ALYHrJ2TRCiUaLkA-JQvoFDS6E99PyGkpa4BWgBDPyQkDBispYEG-vI8pllQqZqQp0L0darYVL6gda2yub77RbY6jj9sBqXugcfwRXawxjTSkTMedH9Bmir-2Kde54DPuz8mzYIeCL47zjHz9-OH-6rq5vft0c3V523iheW2004x3WnRCOilBeQxMBYFKMua4V9g7KbRvGTgF3AWlUHmtZRess72U_Iy8OfRuc_q5w1LNJhaPw2BHTLtiVkIBSM354yTniku26iaSHUifUykZg5ne39j8YFows3WzNrN1M1s3wMxkfQq9Otbv3Ab7v5E_mifg9RGwxdshZDsZLf84ppnQq_nOdwcOJ237iNkUH3H02MeMvpo-xf_d8RtIfJ8z</recordid><startdate>20100401</startdate><enddate>20100401</enddate><creator>Tamura, Satoru</creator><creator>Shimizu, Nobuhiro</creator><creator>Fujiwara, Katsuaki</creator><creator>Kaneko, Masafumi</creator><creator>Kimura, Tominori</creator><creator>Murakami, Nobutoshi</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>20100401</creationdate><title>Bioisostere of valtrate, anti-HIV principle by inhibition for nuclear export of Rev</title><author>Tamura, Satoru ; Shimizu, Nobuhiro ; Fujiwara, Katsuaki ; Kaneko, Masafumi ; Kimura, Tominori ; Murakami, Nobutoshi</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c483t-8b823984945b5506cef26f4e6522b3c6edb548c120b603bf66e6c8859fabad553</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2010</creationdate><topic>Active Transport, Cell Nucleus - drug effects</topic><topic>Anti-HIV</topic><topic>Anti-HIV Agents - chemistry</topic><topic>Anti-HIV Agents - pharmacology</topic><topic>Antibiotics. Antiinfectious agents. Antiparasitic agents</topic><topic>Antiviral agents</topic><topic>Bioisostere</topic><topic>Biological and medical sciences</topic><topic>Gene Products, rev - metabolism</topic><topic>HeLa Cells</topic><topic>HIV Infections - drug therapy</topic><topic>Human immunodeficiency virus</topic><topic>Humans</topic><topic>Iridoid</topic><topic>Iridoids - chemistry</topic><topic>Iridoids - pharmacology</topic><topic>Medical sciences</topic><topic>Molecular Conformation</topic><topic>Pharmacology. Drug treatments</topic><topic>Rev-export inhibitor</topic><topic>Valtrate</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Tamura, Satoru</creatorcontrib><creatorcontrib>Shimizu, Nobuhiro</creatorcontrib><creatorcontrib>Fujiwara, Katsuaki</creatorcontrib><creatorcontrib>Kaneko, Masafumi</creatorcontrib><creatorcontrib>Kimura, Tominori</creatorcontrib><creatorcontrib>Murakami, Nobutoshi</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>Tamura, Satoru</au><au>Shimizu, Nobuhiro</au><au>Fujiwara, Katsuaki</au><au>Kaneko, Masafumi</au><au>Kimura, Tominori</au><au>Murakami, Nobutoshi</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Bioisostere of valtrate, anti-HIV principle by inhibition for nuclear export of Rev</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2010-04-01</date><risdate>2010</risdate><volume>20</volume><issue>7</issue><spage>2159</spage><epage>2162</epage><pages>2159-2162</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>Based on the design from the MO calculation, 5,6-dihydrovaltrate (
2) was synthesized and revealed to be the bioisostere of valtrate (
1) showing anti-HIV activity by inhibition for nuclear export of Rev.
Rational design by the MO calculation disclosed 5,6-dihydrovaltrate (
2) as the bioisostere of valtrate (
1), the Rev-export inhibitor with anti-HIV activity. The synthesis of
2 was accomplished by ingenious use of asymmetric Diels–Alder reaction and stereoselective epoxidation associated with the adjacent hydroxyl group. Because of similar biological potency to
1, the analog
2 should be recognized as a promising scaffold for new anti-HIV agents with an unprecedented mechanism of action, inhibition for nuclear export of Rev protein, in the conventional remedy.</abstract><cop>Amsterdam</cop><pub>Elsevier Ltd</pub><pmid>20207540</pmid><doi>10.1016/j.bmcl.2010.02.038</doi><tpages>4</tpages></addata></record> |
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| ispartof | Bioorganic & medicinal chemistry letters, 2010-04, Vol.20 (7), p.2159-2162 |
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| subjects | Active Transport, Cell Nucleus - drug effects Anti-HIV Anti-HIV Agents - chemistry Anti-HIV Agents - pharmacology Antibiotics. Antiinfectious agents. Antiparasitic agents Antiviral agents Bioisostere Biological and medical sciences Gene Products, rev - metabolism HeLa Cells HIV Infections - drug therapy Human immunodeficiency virus Humans Iridoid Iridoids - chemistry Iridoids - pharmacology Medical sciences Molecular Conformation Pharmacology. Drug treatments Rev-export inhibitor Valtrate |
| title | Bioisostere of valtrate, anti-HIV principle by inhibition for nuclear export of Rev |
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