Design, Synthesis, and Cytotoxic Activity of Michael Acceptors and Enol Esters in the Benzo[b]acronycine Series
A series of 2-acyl-6-methoxy-3,3,14-trimethyl-3,14-dihydro-7H-benzo[b]pyrano[3,2-h]acridin-7-ones (4—6) was prepared by treatment of 6-methoxy-3,3,14-trimethyl-3,14-dihydro-7H-benzo[b]pyrano[3,2-h]acridin-7-one (3) with an excess of an appropriate acyl chloride in the presence of aluminum chloride....
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| Veröffentlicht in: | Chemical & Pharmaceutical Bulletin 2005, Vol.53(8), pp.919-922 |
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| creator | Mai, Huong Doan Thi Gaslonde, Thomas Michel, Sylvie Koch, Michel Tillequin, François Bailly, Christian David-Cordonnier, Marie-Hélène Pfeiffer, Bruno Léonce, Stéphane Pierré, Alain |
| description | A series of 2-acyl-6-methoxy-3,3,14-trimethyl-3,14-dihydro-7H-benzo[b]pyrano[3,2-h]acridin-7-ones (4—6) was prepared by treatment of 6-methoxy-3,3,14-trimethyl-3,14-dihydro-7H-benzo[b]pyrano[3,2-h]acridin-7-one (3) with an excess of an appropriate acyl chloride in the presence of aluminum chloride. Treatment of (±)-cis-1-hydroxy-2-acyloxy-6-methoxy-3,3,14-trimethyl-1,2,3,14-tetrahydro-7H-benzo[b]pyrano[3,2-h]acridin-7-ones (9, 10) or (±)-cis-1,2-diacyloxy-6-methoxy-3,3,14-trimethyl-1,2,3,14-tetrahydro-7H-benzo[b]pyrano[3,2-h]acridin-7-ones (2, 11) with hydrochloric acid gave the corresponding 2-acyloxy-6-methoxy-3,3,14-trimethyl-3,14-dihydro-7H-benzo[b]pyrano[3,2-h]acridin-7-ones, exemplified by acetate 7 and butyrate 8. None of the Michael acceptors 4—6 showed significant antiproliferative activity. Enol esters 7 and 8 were markedly cytotoxic toward L1210 leukemia cells, with IC50 values within the same range of magnitude as (±)-cis-1,2-diacetoxy-6-methoxy-3,3,14-trimethyl-1,2,3,14-tetrahydro-7H-benzo[b]pyrano[3,2-h]acridin-7-one (S23906-1), currently under phase I clinical trials. In contrast with S23906-1, enol esters 7 and 8 were not reactive toward purified DNA. |
| doi_str_mv | 10.1248/cpb.53.919 |
| format | Article |
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M. R. /C. N. R. S. n ; bINSERM U- et Laboratoire de Pharmacologie Antitumorale du Centre Oscar Lambret ; Faculte des Sciences Pharmaceutiques et Biologiques ; IRCL ; cInstitut de Recherches Servier ; Division Recherche Cancerologie</creatorcontrib><description>A series of 2-acyl-6-methoxy-3,3,14-trimethyl-3,14-dihydro-7H-benzo[b]pyrano[3,2-h]acridin-7-ones (4—6) was prepared by treatment of 6-methoxy-3,3,14-trimethyl-3,14-dihydro-7H-benzo[b]pyrano[3,2-h]acridin-7-one (3) with an excess of an appropriate acyl chloride in the presence of aluminum chloride. Treatment of (±)-cis-1-hydroxy-2-acyloxy-6-methoxy-3,3,14-trimethyl-1,2,3,14-tetrahydro-7H-benzo[b]pyrano[3,2-h]acridin-7-ones (9, 10) or (±)-cis-1,2-diacyloxy-6-methoxy-3,3,14-trimethyl-1,2,3,14-tetrahydro-7H-benzo[b]pyrano[3,2-h]acridin-7-ones (2, 11) with hydrochloric acid gave the corresponding 2-acyloxy-6-methoxy-3,3,14-trimethyl-3,14-dihydro-7H-benzo[b]pyrano[3,2-h]acridin-7-ones, exemplified by acetate 7 and butyrate 8. None of the Michael acceptors 4—6 showed significant antiproliferative activity. Enol esters 7 and 8 were markedly cytotoxic toward L1210 leukemia cells, with IC50 values within the same range of magnitude as (±)-cis-1,2-diacetoxy-6-methoxy-3,3,14-trimethyl-1,2,3,14-tetrahydro-7H-benzo[b]pyrano[3,2-h]acridin-7-one (S23906-1), currently under phase I clinical trials. In contrast with S23906-1, enol esters 7 and 8 were not reactive toward purified DNA.</description><identifier>ISSN: 0009-2363</identifier><identifier>EISSN: 1347-5223</identifier><identifier>DOI: 10.1248/cpb.53.919</identifier><identifier>PMID: 16079520</identifier><language>eng</language><publisher>Japan: The Pharmaceutical Society of Japan</publisher><subject>Acronine - analogs & derivatives ; Acronine - chemical synthesis ; Acronine - chemistry ; Acronine - pharmacology ; acronycine ; Animals ; Antineoplastic Agents - chemical synthesis ; Antineoplastic Agents - chemistry ; Antineoplastic Agents - pharmacology ; benzo[b]acronycine ; Cell Cycle ; Cell Line, Tumor ; cytotoxicity ; Drug Design ; Esters ; Leukemia L1210 - pathology ; Magnetic Resonance Spectroscopy ; Mice ; Spectrophotometry, Ultraviolet</subject><ispartof>Chemical and Pharmaceutical Bulletin, 2005, Vol.53(8), pp.919-922</ispartof><rights>2005 The Pharmaceutical Society of Japan</rights><rights>Copyright Japan Science and Technology Agency 2005</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c630t-e2bc21296639b0ba29c270a29401513d41f9436bc0d0af2c48bacfcb5e4337ee3</citedby><cites>FETCH-LOGICAL-c630t-e2bc21296639b0ba29c270a29401513d41f9436bc0d0af2c48bacfcb5e4337ee3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,1883,4024,27923,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/16079520$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Mai, Huong Doan Thi</creatorcontrib><creatorcontrib>Gaslonde, Thomas</creatorcontrib><creatorcontrib>Michel, Sylvie</creatorcontrib><creatorcontrib>Koch, Michel</creatorcontrib><creatorcontrib>Tillequin, François</creatorcontrib><creatorcontrib>Bailly, Christian</creatorcontrib><creatorcontrib>David-Cordonnier, Marie-Hélène</creatorcontrib><creatorcontrib>Pfeiffer, Bruno</creatorcontrib><creatorcontrib>Léonce, Stéphane</creatorcontrib><creatorcontrib>Pierré, Alain</creatorcontrib><creatorcontrib>aLaboratoire de Pharmacognosie de l'Universite Rene Descartes</creatorcontrib><creatorcontrib>U. M. R. /C. N. R. S. n</creatorcontrib><creatorcontrib>bINSERM U- et Laboratoire de Pharmacologie Antitumorale du Centre Oscar Lambret</creatorcontrib><creatorcontrib>Faculte des Sciences Pharmaceutiques et Biologiques</creatorcontrib><creatorcontrib>IRCL</creatorcontrib><creatorcontrib>cInstitut de Recherches Servier</creatorcontrib><creatorcontrib>Division Recherche Cancerologie</creatorcontrib><title>Design, Synthesis, and Cytotoxic Activity of Michael Acceptors and Enol Esters in the Benzo[b]acronycine Series</title><title>Chemical & Pharmaceutical Bulletin</title><addtitle>Chem. Pharm. Bull.</addtitle><description>A series of 2-acyl-6-methoxy-3,3,14-trimethyl-3,14-dihydro-7H-benzo[b]pyrano[3,2-h]acridin-7-ones (4—6) was prepared by treatment of 6-methoxy-3,3,14-trimethyl-3,14-dihydro-7H-benzo[b]pyrano[3,2-h]acridin-7-one (3) with an excess of an appropriate acyl chloride in the presence of aluminum chloride. Treatment of (±)-cis-1-hydroxy-2-acyloxy-6-methoxy-3,3,14-trimethyl-1,2,3,14-tetrahydro-7H-benzo[b]pyrano[3,2-h]acridin-7-ones (9, 10) or (±)-cis-1,2-diacyloxy-6-methoxy-3,3,14-trimethyl-1,2,3,14-tetrahydro-7H-benzo[b]pyrano[3,2-h]acridin-7-ones (2, 11) with hydrochloric acid gave the corresponding 2-acyloxy-6-methoxy-3,3,14-trimethyl-3,14-dihydro-7H-benzo[b]pyrano[3,2-h]acridin-7-ones, exemplified by acetate 7 and butyrate 8. None of the Michael acceptors 4—6 showed significant antiproliferative activity. Enol esters 7 and 8 were markedly cytotoxic toward L1210 leukemia cells, with IC50 values within the same range of magnitude as (±)-cis-1,2-diacetoxy-6-methoxy-3,3,14-trimethyl-1,2,3,14-tetrahydro-7H-benzo[b]pyrano[3,2-h]acridin-7-one (S23906-1), currently under phase I clinical trials. In contrast with S23906-1, enol esters 7 and 8 were not reactive toward purified DNA.</description><subject>Acronine - analogs & derivatives</subject><subject>Acronine - chemical synthesis</subject><subject>Acronine - chemistry</subject><subject>Acronine - pharmacology</subject><subject>acronycine</subject><subject>Animals</subject><subject>Antineoplastic Agents - chemical synthesis</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>benzo[b]acronycine</subject><subject>Cell Cycle</subject><subject>Cell Line, Tumor</subject><subject>cytotoxicity</subject><subject>Drug Design</subject><subject>Esters</subject><subject>Leukemia L1210 - pathology</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Mice</subject><subject>Spectrophotometry, Ultraviolet</subject><issn>0009-2363</issn><issn>1347-5223</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2005</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpFUMFuEzEUtBAVDYULH4AscUPd9NneXe-eUAmhrVTEoXBCyPI6bxtHGzu1HcTy9ThsaA9-Y_uNZ56HkDcM5oyXzYXZdfNKzFvWPiMzJkpZVJyL52QGAG3BRS1OycsYNwC8AilekFNWg2wrDjPiP2G09-6c3o0urfM-nlPtVnQxJp_8b2vopUn2l00j9T39Ys1a45DvDO6SD_Efd-n8QJcxYT5bR7MM_Yjuj__R_dQmeDca65DeYbAYX5GTXg8RXx_xjHz_vPy2uC5uv17dLC5vC1MLSAXyznDG27oWbQed5q3hEjKUwComViXr21LUnYEV6J6bsum06U1XYSmERBRn5N2kuwv-YY8xqY3fB5ctFStrEE3dSJlZ7ydWHjPGgL3aBbvVYVQM1CFblbNVlVA520x-e5Tcd1tcPVGPYWbC1UTIXWv04N2QP_5kbKI0a9xaxQEqlZeAJkOrIMvnwjkDyevmYPVhUtrEpO_x0UqHZM2A_6dqpnJ4_dhZ66DQib9qqKHz</recordid><startdate>2005</startdate><enddate>2005</enddate><creator>Mai, Huong Doan Thi</creator><creator>Gaslonde, Thomas</creator><creator>Michel, Sylvie</creator><creator>Koch, Michel</creator><creator>Tillequin, François</creator><creator>Bailly, Christian</creator><creator>David-Cordonnier, Marie-Hélène</creator><creator>Pfeiffer, Bruno</creator><creator>Léonce, Stéphane</creator><creator>Pierré, Alain</creator><general>The Pharmaceutical Society of Japan</general><general>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></search><sort><creationdate>2005</creationdate><title>Design, Synthesis, and Cytotoxic Activity of Michael Acceptors and Enol Esters in the Benzo[b]acronycine Series</title><author>Mai, Huong Doan Thi ; Gaslonde, Thomas ; Michel, Sylvie ; Koch, Michel ; Tillequin, François ; Bailly, Christian ; David-Cordonnier, Marie-Hélène ; Pfeiffer, Bruno ; Léonce, Stéphane ; Pierré, Alain</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c630t-e2bc21296639b0ba29c270a29401513d41f9436bc0d0af2c48bacfcb5e4337ee3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2005</creationdate><topic>Acronine - analogs & derivatives</topic><topic>Acronine - chemical synthesis</topic><topic>Acronine - chemistry</topic><topic>Acronine - pharmacology</topic><topic>acronycine</topic><topic>Animals</topic><topic>Antineoplastic Agents - chemical synthesis</topic><topic>Antineoplastic Agents - chemistry</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>benzo[b]acronycine</topic><topic>Cell Cycle</topic><topic>Cell Line, Tumor</topic><topic>cytotoxicity</topic><topic>Drug Design</topic><topic>Esters</topic><topic>Leukemia L1210 - pathology</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Mice</topic><topic>Spectrophotometry, Ultraviolet</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Mai, Huong Doan Thi</creatorcontrib><creatorcontrib>Gaslonde, Thomas</creatorcontrib><creatorcontrib>Michel, Sylvie</creatorcontrib><creatorcontrib>Koch, Michel</creatorcontrib><creatorcontrib>Tillequin, François</creatorcontrib><creatorcontrib>Bailly, Christian</creatorcontrib><creatorcontrib>David-Cordonnier, Marie-Hélène</creatorcontrib><creatorcontrib>Pfeiffer, Bruno</creatorcontrib><creatorcontrib>Léonce, Stéphane</creatorcontrib><creatorcontrib>Pierré, Alain</creatorcontrib><creatorcontrib>aLaboratoire de Pharmacognosie de l'Universite Rene Descartes</creatorcontrib><creatorcontrib>U. M. R. /C. N. R. S. n</creatorcontrib><creatorcontrib>bINSERM U- et Laboratoire de Pharmacologie Antitumorale du Centre Oscar Lambret</creatorcontrib><creatorcontrib>Faculte des Sciences Pharmaceutiques et Biologiques</creatorcontrib><creatorcontrib>IRCL</creatorcontrib><creatorcontrib>cInstitut de Recherches Servier</creatorcontrib><creatorcontrib>Division Recherche Cancerologie</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><jtitle>Chemical & Pharmaceutical Bulletin</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Mai, Huong Doan Thi</au><au>Gaslonde, Thomas</au><au>Michel, Sylvie</au><au>Koch, Michel</au><au>Tillequin, François</au><au>Bailly, Christian</au><au>David-Cordonnier, Marie-Hélène</au><au>Pfeiffer, Bruno</au><au>Léonce, Stéphane</au><au>Pierré, Alain</au><aucorp>aLaboratoire de Pharmacognosie de l'Universite Rene Descartes</aucorp><aucorp>U. M. R. /C. N. R. S. n</aucorp><aucorp>bINSERM U- et Laboratoire de Pharmacologie Antitumorale du Centre Oscar Lambret</aucorp><aucorp>Faculte des Sciences Pharmaceutiques et Biologiques</aucorp><aucorp>IRCL</aucorp><aucorp>cInstitut de Recherches Servier</aucorp><aucorp>Division Recherche Cancerologie</aucorp><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Design, Synthesis, and Cytotoxic Activity of Michael Acceptors and Enol Esters in the Benzo[b]acronycine Series</atitle><jtitle>Chemical & Pharmaceutical Bulletin</jtitle><addtitle>Chem. Pharm. Bull.</addtitle><date>2005</date><risdate>2005</risdate><volume>53</volume><issue>8</issue><spage>919</spage><epage>922</epage><pages>919-922</pages><issn>0009-2363</issn><eissn>1347-5223</eissn><abstract>A series of 2-acyl-6-methoxy-3,3,14-trimethyl-3,14-dihydro-7H-benzo[b]pyrano[3,2-h]acridin-7-ones (4—6) was prepared by treatment of 6-methoxy-3,3,14-trimethyl-3,14-dihydro-7H-benzo[b]pyrano[3,2-h]acridin-7-one (3) with an excess of an appropriate acyl chloride in the presence of aluminum chloride. Treatment of (±)-cis-1-hydroxy-2-acyloxy-6-methoxy-3,3,14-trimethyl-1,2,3,14-tetrahydro-7H-benzo[b]pyrano[3,2-h]acridin-7-ones (9, 10) or (±)-cis-1,2-diacyloxy-6-methoxy-3,3,14-trimethyl-1,2,3,14-tetrahydro-7H-benzo[b]pyrano[3,2-h]acridin-7-ones (2, 11) with hydrochloric acid gave the corresponding 2-acyloxy-6-methoxy-3,3,14-trimethyl-3,14-dihydro-7H-benzo[b]pyrano[3,2-h]acridin-7-ones, exemplified by acetate 7 and butyrate 8. None of the Michael acceptors 4—6 showed significant antiproliferative activity. Enol esters 7 and 8 were markedly cytotoxic toward L1210 leukemia cells, with IC50 values within the same range of magnitude as (±)-cis-1,2-diacetoxy-6-methoxy-3,3,14-trimethyl-1,2,3,14-tetrahydro-7H-benzo[b]pyrano[3,2-h]acridin-7-one (S23906-1), currently under phase I clinical trials. In contrast with S23906-1, enol esters 7 and 8 were not reactive toward purified DNA.</abstract><cop>Japan</cop><pub>The Pharmaceutical Society of Japan</pub><pmid>16079520</pmid><doi>10.1248/cpb.53.919</doi><tpages>4</tpages><oa>free_for_read</oa></addata></record> |
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| subjects | Acronine - analogs & derivatives Acronine - chemical synthesis Acronine - chemistry Acronine - pharmacology acronycine Animals Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacology benzo[b]acronycine Cell Cycle Cell Line, Tumor cytotoxicity Drug Design Esters Leukemia L1210 - pathology Magnetic Resonance Spectroscopy Mice Spectrophotometry, Ultraviolet |
| title | Design, Synthesis, and Cytotoxic Activity of Michael Acceptors and Enol Esters in the Benzo[b]acronycine Series |
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