Synthesis, antiproliferative activity in cancer cells and theoretical studies of novel 6α,7β-dihydroxyvouacapan-17β-oic acid Mannich base derivatives
Natural products are great prototypes for the design of new anticancer agents. The plant-derived natural product 6α,7β-dihydroxyvouacapan-17β-oic acid ( 1) is promising for the development of more potent antiproliferative agents against human cancer cells. Indeed, its lactone derivative 6α-hydroxyvo...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry 2010-12, Vol.18 (23), p.8172-8177 |
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| creator | Euzébio, Felipe P.G. Santos, Flávio J.L. dos Piló-Veloso, Dorila Alcântara, Antônio F.C. Ruiz, Ana L.T.G. Carvalho, João Ernesto de Foglio, Mary A. Ferreira-Alves, Dalton L. Fátima, Ângelo de |
| description | Natural products are great prototypes for the design of new anticancer agents. The plant-derived natural product 6α,7β-dihydroxyvouacapan-17β-oic acid (
1) is promising for the development of more potent antiproliferative agents against human cancer cells. Indeed, its lactone derivative 6α-hydroxyvouacapan-7β,17β-lactone (
2), a non-natural furanoditerpene, exhibited higher anticancer activity than compound
1. Herein, we describe the synthesis and antiproliferative activity of six new Mannich derivatives of compound
2 against nine cancer cell lines. Overall, our results revealed that Mannich derivatives
3–
8 were more potent than compound
2 in inhibiting the proliferation of cancer cells. Theoretical studies also supported our findings, revealing the nucleophilic character of furan ring as an important feature for antiproliferative activity of the studied Mannich derivatives. |
| doi_str_mv | 10.1016/j.bmc.2010.10.015 |
| format | Article |
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1) is promising for the development of more potent antiproliferative agents against human cancer cells. Indeed, its lactone derivative 6α-hydroxyvouacapan-7β,17β-lactone (
2), a non-natural furanoditerpene, exhibited higher anticancer activity than compound
1. Herein, we describe the synthesis and antiproliferative activity of six new Mannich derivatives of compound
2 against nine cancer cell lines. Overall, our results revealed that Mannich derivatives
3–
8 were more potent than compound
2 in inhibiting the proliferation of cancer cells. Theoretical studies also supported our findings, revealing the nucleophilic character of furan ring as an important feature for antiproliferative activity of the studied Mannich derivatives.</description><identifier>ISSN: 0968-0896</identifier><identifier>EISSN: 1464-3391</identifier><identifier>DOI: 10.1016/j.bmc.2010.10.015</identifier><identifier>PMID: 21041092</identifier><language>eng</language><publisher>Amsterdam: Elsevier Ltd</publisher><subject>6α,7β-Dihydroxyvouacapan-17β-oic acid ; Anticancer agents ; Antineoplastic agents ; Antineoplastic Agents - chemical synthesis ; Antineoplastic Agents - chemistry ; Antineoplastic Agents - pharmacology ; Biological and medical sciences ; Cell Line, Tumor ; Diterpenes - chemistry ; Drug Screening Assays, Antitumor ; Fabaceae - chemistry ; Fruit - chemistry ; Furanoditerpene derivatives ; Furans - chemistry ; General aspects ; Humans ; Lactones - chemistry ; Mannich base ; Mannich Bases - chemical synthesis ; Mannich Bases - chemistry ; Mannich Bases - pharmacology ; Medical sciences ; Models, Molecular ; Natural products ; Pharmacology. Drug treatments ; Quantum Theory</subject><ispartof>Bioorganic & medicinal chemistry, 2010-12, Vol.18 (23), p.8172-8177</ispartof><rights>2010 Elsevier Ltd</rights><rights>2015 INIST-CNRS</rights><rights>Copyright © 2010 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3405-3500d1e367eb418665a3cea50b76e11e31be4b0afd7de30332dda591cfe12fd13</citedby><cites>FETCH-LOGICAL-c3405-3500d1e367eb418665a3cea50b76e11e31be4b0afd7de30332dda591cfe12fd13</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.bmc.2010.10.015$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,777,781,3537,27905,27906,45976</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=23530205$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/21041092$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Euzébio, Felipe P.G.</creatorcontrib><creatorcontrib>Santos, Flávio J.L. dos</creatorcontrib><creatorcontrib>Piló-Veloso, Dorila</creatorcontrib><creatorcontrib>Alcântara, Antônio F.C.</creatorcontrib><creatorcontrib>Ruiz, Ana L.T.G.</creatorcontrib><creatorcontrib>Carvalho, João Ernesto de</creatorcontrib><creatorcontrib>Foglio, Mary A.</creatorcontrib><creatorcontrib>Ferreira-Alves, Dalton L.</creatorcontrib><creatorcontrib>Fátima, Ângelo de</creatorcontrib><title>Synthesis, antiproliferative activity in cancer cells and theoretical studies of novel 6α,7β-dihydroxyvouacapan-17β-oic acid Mannich base derivatives</title><title>Bioorganic & medicinal chemistry</title><addtitle>Bioorg Med Chem</addtitle><description>Natural products are great prototypes for the design of new anticancer agents. The plant-derived natural product 6α,7β-dihydroxyvouacapan-17β-oic acid (
1) is promising for the development of more potent antiproliferative agents against human cancer cells. Indeed, its lactone derivative 6α-hydroxyvouacapan-7β,17β-lactone (
2), a non-natural furanoditerpene, exhibited higher anticancer activity than compound
1. Herein, we describe the synthesis and antiproliferative activity of six new Mannich derivatives of compound
2 against nine cancer cell lines. Overall, our results revealed that Mannich derivatives
3–
8 were more potent than compound
2 in inhibiting the proliferation of cancer cells. Theoretical studies also supported our findings, revealing the nucleophilic character of furan ring as an important feature for antiproliferative activity of the studied Mannich derivatives.</description><subject>6α,7β-Dihydroxyvouacapan-17β-oic acid</subject><subject>Anticancer agents</subject><subject>Antineoplastic agents</subject><subject>Antineoplastic Agents - chemical synthesis</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Biological and medical sciences</subject><subject>Cell Line, Tumor</subject><subject>Diterpenes - chemistry</subject><subject>Drug Screening Assays, Antitumor</subject><subject>Fabaceae - chemistry</subject><subject>Fruit - chemistry</subject><subject>Furanoditerpene derivatives</subject><subject>Furans - chemistry</subject><subject>General aspects</subject><subject>Humans</subject><subject>Lactones - chemistry</subject><subject>Mannich base</subject><subject>Mannich Bases - chemical synthesis</subject><subject>Mannich Bases - chemistry</subject><subject>Mannich Bases - pharmacology</subject><subject>Medical sciences</subject><subject>Models, Molecular</subject><subject>Natural products</subject><subject>Pharmacology. Drug treatments</subject><subject>Quantum Theory</subject><issn>0968-0896</issn><issn>1464-3391</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2010</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kc9u1DAQxi1ERZfCA3BBvqBemmUcJ85GnFDFP6mIA3C2HHuinVU2XuwkIm_S14AH6TPV6S5w4zTy-DefPd_H2AsBawFCvd6tm71d5_BwXoMoH7GVKFSRSVmLx2wFtdpksKnVOXsa4w4A8qIWT9h5LqAQUOcrdvt17octRopX3PQDHYLvqMVgBpqQG5sKDTOnnlvTWwzcYtfFhDqexnzAgazpeBxGRxi5b3nvJ-y4uvt1Vd39zhxtZxf8z3nyo7HmYPpMLH1PNqmT459N35Pd8sZE5A4DTQ9Px2fsrDVdxOenesG-v3_37fpjdvPlw6frtzeZlQWUmSwBnECpKmwKsVGqNNKiKaGpFIp0IRosGjCtqxxKkDJ3zpS1sC2KvHVCXrDLo27a_MeIcdB7isuSpkc_Rl2popTVplpIcSRt8DEGbPUh0N6EWQvQSx56p1MeesljaaU80szLk_rY7NH9nfgTQAJenQATk5FtSC5T_MfJUkIOi9CbI4fJi4kw6GgJUyKOAtpBO0__-cY9nQys_A</recordid><startdate>20101201</startdate><enddate>20101201</enddate><creator>Euzébio, Felipe P.G.</creator><creator>Santos, Flávio J.L. dos</creator><creator>Piló-Veloso, Dorila</creator><creator>Alcântara, Antônio F.C.</creator><creator>Ruiz, Ana L.T.G.</creator><creator>Carvalho, João Ernesto de</creator><creator>Foglio, Mary A.</creator><creator>Ferreira-Alves, Dalton L.</creator><creator>Fátima, Ângelo de</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></search><sort><creationdate>20101201</creationdate><title>Synthesis, antiproliferative activity in cancer cells and theoretical studies of novel 6α,7β-dihydroxyvouacapan-17β-oic acid Mannich base derivatives</title><author>Euzébio, Felipe P.G. ; Santos, Flávio J.L. dos ; Piló-Veloso, Dorila ; Alcântara, Antônio F.C. ; Ruiz, Ana L.T.G. ; Carvalho, João Ernesto de ; Foglio, Mary A. ; Ferreira-Alves, Dalton L. ; Fátima, Ângelo de</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3405-3500d1e367eb418665a3cea50b76e11e31be4b0afd7de30332dda591cfe12fd13</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2010</creationdate><topic>6α,7β-Dihydroxyvouacapan-17β-oic acid</topic><topic>Anticancer agents</topic><topic>Antineoplastic agents</topic><topic>Antineoplastic Agents - chemical synthesis</topic><topic>Antineoplastic Agents - chemistry</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>Biological and medical sciences</topic><topic>Cell Line, Tumor</topic><topic>Diterpenes - chemistry</topic><topic>Drug Screening Assays, Antitumor</topic><topic>Fabaceae - chemistry</topic><topic>Fruit - chemistry</topic><topic>Furanoditerpene derivatives</topic><topic>Furans - chemistry</topic><topic>General aspects</topic><topic>Humans</topic><topic>Lactones - chemistry</topic><topic>Mannich base</topic><topic>Mannich Bases - chemical synthesis</topic><topic>Mannich Bases - chemistry</topic><topic>Mannich Bases - pharmacology</topic><topic>Medical sciences</topic><topic>Models, Molecular</topic><topic>Natural products</topic><topic>Pharmacology. 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The plant-derived natural product 6α,7β-dihydroxyvouacapan-17β-oic acid (
1) is promising for the development of more potent antiproliferative agents against human cancer cells. Indeed, its lactone derivative 6α-hydroxyvouacapan-7β,17β-lactone (
2), a non-natural furanoditerpene, exhibited higher anticancer activity than compound
1. Herein, we describe the synthesis and antiproliferative activity of six new Mannich derivatives of compound
2 against nine cancer cell lines. Overall, our results revealed that Mannich derivatives
3–
8 were more potent than compound
2 in inhibiting the proliferation of cancer cells. Theoretical studies also supported our findings, revealing the nucleophilic character of furan ring as an important feature for antiproliferative activity of the studied Mannich derivatives.</abstract><cop>Amsterdam</cop><pub>Elsevier Ltd</pub><pmid>21041092</pmid><doi>10.1016/j.bmc.2010.10.015</doi><tpages>6</tpages><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0968-0896 |
| ispartof | Bioorganic & medicinal chemistry, 2010-12, Vol.18 (23), p.8172-8177 |
| issn | 0968-0896 1464-3391 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_764537871 |
| source | MEDLINE; ScienceDirect Journals (5 years ago - present) |
| subjects | 6α,7β-Dihydroxyvouacapan-17β-oic acid Anticancer agents Antineoplastic agents Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacology Biological and medical sciences Cell Line, Tumor Diterpenes - chemistry Drug Screening Assays, Antitumor Fabaceae - chemistry Fruit - chemistry Furanoditerpene derivatives Furans - chemistry General aspects Humans Lactones - chemistry Mannich base Mannich Bases - chemical synthesis Mannich Bases - chemistry Mannich Bases - pharmacology Medical sciences Models, Molecular Natural products Pharmacology. Drug treatments Quantum Theory |
| title | Synthesis, antiproliferative activity in cancer cells and theoretical studies of novel 6α,7β-dihydroxyvouacapan-17β-oic acid Mannich base derivatives |
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