title: Semisynthesis and antitumoral activity of 2-acetylfuranonaphthoquinone and other naphthoquinone derivatives from lapachol.
abstract: Ozonolysis of lapachol (1), resulting in an unusual formation of a potent antitumor agent 2-acetylfuranonaphthoquinone (3) along with the expected aldehyde 6, is described. The reaction of lapachol (1) with CAN in dry acetonitrile leading to biologically active furanonaphthoquinones is also reported. The antitumoral activity of the tested compounds on human DU-145 prostate carcinoma cells was evaluated following XTT assay. The results revealed that 2-(1-methylethenyl)-2,3-dihydronaphtho[2,3-b]furan-4,9-dione (5), beta-lapachone (10) and dehydro-beta-lapachone diacetate (11) showed 100% inhibition at 25 microg/ml. All the tested samples showed dose-dependent activity.
authors.affiliation: Department of Chemistry, Indian Institute of Technology Madras, Chennai 600 036, India.
authors.forename: Kenneth O
authors.initials: KO
authors.lastname: Eyong
authors.forename: Ponminor S
authors.initials: PS
authors.lastname: Kumar
authors.forename: Victor
authors.initials: V
authors.lastname: Kuete
authors.forename: Gabriel N
authors.initials: GN
authors.lastname: Folefoc
authors.forename: Ephriam A
authors.initials: EA
authors.lastname: Nkengfack
authors.forename: Sundarababu
authors.initials: S
authors.lastname: Baskaran
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D045744:Cell Line, Tumor; D002626:Chemistry, Pharmaceutical / Q000379:methods; D004305:Dose-Response Relationship, Drug; D015195:Drug Design; D004354:Drug Screening Assays, Antitumor; D005663:Furans / Q000138:chemical synthesis* / Q000494:pharmacology*; D006801:Humans; D008956:Models, Chemical; D009285:Naphthoquinones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D009369:Neoplasms / Q000188:drug therapy; D010126:Ozone / Q000737:chemistry; D010936:Plant Extracts / Q000378:metabolism*; D011809:Quinones / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: C508754:2-acetylfuranonaphthoquinone; D000447:Aldehydes; D000970:Antineoplastic Agents; D005663:Furans; D009285:Naphthoquinones; D010936:Plant Extracts; D011809:Quinones; D010126:Ozone; C008252:lapachol