3-Arylamino and 3-Alkoxy-nor-β-lapachone Derivatives: Synthesis and Cytotoxicity against Cancer Cell Lines
Several 3-arylamino and 3-alkoxy-nor-β-lapachone derivatives were synthesized in moderate to high yields and found to be highly potent against cancer cells SF295 (central nervous system), HCT8 (colon), MDA-MB435 (melanoma), and HL60 (leukemia), with IC50 below 2 μM. The arylamino para-nitro and the...
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| Veröffentlicht in: | Journal of medicinal chemistry 2010-01, Vol.53 (1), p.504-508 |
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| creator | da Silva Júnior, Eufrânio N de Deus, Clara F Cavalcanti, Bruno C Pessoa, Cláudia Costa-Lotufo, Letícia V Montenegro, Raquel C de Moraes, Manoel O Pinto, Maria do Carmo F. R de Simone, Carlos A Ferreira, Vitor F Goulart, Marilia O. F Andrade, Carlos Kleber Z Pinto, Antônio V |
| description | Several 3-arylamino and 3-alkoxy-nor-β-lapachone derivatives were synthesized in moderate to high yields and found to be highly potent against cancer cells SF295 (central nervous system), HCT8 (colon), MDA-MB435 (melanoma), and HL60 (leukemia), with IC50 below 2 μM. The arylamino para-nitro and the 2,4-dimethoxy substituted naphthoquinones showed the best cytoxicity profile, while the ortho-nitro and the 2,4-dimethoxy substituted ones were more selective than doxorubicin and similar to the precursor lapachones, thus emerging as promising new lead compounds in anticancer drug development. |
| doi_str_mv | 10.1021/jm900865m |
| format | Article |
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The arylamino para-nitro and the 2,4-dimethoxy substituted naphthoquinones showed the best cytoxicity profile, while the ortho-nitro and the 2,4-dimethoxy substituted ones were more selective than doxorubicin and similar to the precursor lapachones, thus emerging as promising new lead compounds in anticancer drug development.</description><identifier>ISSN: 0022-2623</identifier><identifier>EISSN: 1520-4804</identifier><identifier>DOI: 10.1021/jm900865m</identifier><identifier>PMID: 19947600</identifier><identifier>CODEN: JMCMAR</identifier><language>eng</language><publisher>Columbus, OH: American Chemical Society</publisher><subject>Antineoplastic agents ; Biological and medical sciences ; Cell Line, Tumor ; Cell Proliferation - drug effects ; Crystallography, X-Ray ; Drug Screening Assays, Antitumor ; General aspects ; Humans ; Medical sciences ; Models, Molecular ; Molecular Structure ; Naphthoquinones - chemical synthesis ; Naphthoquinones - chemistry ; Naphthoquinones - pharmacology ; Naphthoquinones - toxicity ; Pharmacology. 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F</creatorcontrib><creatorcontrib>Andrade, Carlos Kleber Z</creatorcontrib><creatorcontrib>Pinto, Antônio V</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><jtitle>Journal of medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>da Silva Júnior, Eufrânio N</au><au>de Deus, Clara F</au><au>Cavalcanti, Bruno C</au><au>Pessoa, Cláudia</au><au>Costa-Lotufo, Letícia V</au><au>Montenegro, Raquel C</au><au>de Moraes, Manoel O</au><au>Pinto, Maria do Carmo F. R</au><au>de Simone, Carlos A</au><au>Ferreira, Vitor F</au><au>Goulart, Marilia O. F</au><au>Andrade, Carlos Kleber Z</au><au>Pinto, Antônio V</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>3-Arylamino and 3-Alkoxy-nor-β-lapachone Derivatives: Synthesis and Cytotoxicity against Cancer Cell Lines</atitle><jtitle>Journal of medicinal chemistry</jtitle><addtitle>J. Med. Chem</addtitle><date>2010-01-14</date><risdate>2010</risdate><volume>53</volume><issue>1</issue><spage>504</spage><epage>508</epage><pages>504-508</pages><issn>0022-2623</issn><eissn>1520-4804</eissn><coden>JMCMAR</coden><abstract>Several 3-arylamino and 3-alkoxy-nor-β-lapachone derivatives were synthesized in moderate to high yields and found to be highly potent against cancer cells SF295 (central nervous system), HCT8 (colon), MDA-MB435 (melanoma), and HL60 (leukemia), with IC50 below 2 μM. The arylamino para-nitro and the 2,4-dimethoxy substituted naphthoquinones showed the best cytoxicity profile, while the ortho-nitro and the 2,4-dimethoxy substituted ones were more selective than doxorubicin and similar to the precursor lapachones, thus emerging as promising new lead compounds in anticancer drug development.</abstract><cop>Columbus, OH</cop><pub>American Chemical Society</pub><pmid>19947600</pmid><doi>10.1021/jm900865m</doi><tpages>5</tpages></addata></record> |
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| ispartof | Journal of medicinal chemistry, 2010-01, Vol.53 (1), p.504-508 |
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| subjects | Antineoplastic agents Biological and medical sciences Cell Line, Tumor Cell Proliferation - drug effects Crystallography, X-Ray Drug Screening Assays, Antitumor General aspects Humans Medical sciences Models, Molecular Molecular Structure Naphthoquinones - chemical synthesis Naphthoquinones - chemistry Naphthoquinones - pharmacology Naphthoquinones - toxicity Pharmacology. Drug treatments Stereoisomerism Structure-Activity Relationship |
| title | 3-Arylamino and 3-Alkoxy-nor-β-lapachone Derivatives: Synthesis and Cytotoxicity against Cancer Cell Lines |
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