Semisynthesis and antitumoral activity of 2-acetylfuranonaphthoquinone and other naphthoquinone derivatives from lapachol.
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.
Eyong
Kenneth O
KO
Department of Chemistry, Indian Institute of Technology Madras, Chennai 600 036, India.
Kumar
Ponminor S
PS
Kuete
Victor
V
Folefoc
Gabriel N
GN
Nkengfack
Ephriam A
EA
Baskaran
Sundarababu
S
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
C508754:2-acetylfuranonaphthoquinone; D000447:Aldehydes; D000970:Antineoplastic Agents; D005663:Furans; D009285:Naphthoquinones; D010936:Plant Extracts; D011809:Quinones; D010126:Ozone; C008252:lapachol