title: First stereoselective total synthesis and anticancer activity of new amide alkaloids of roots of pepper.
abstract: The first stereoselective total synthesis of new natural amide alkaloids 1-3 have been achieved from commercially available starting materials. Wittig olefination, Sharpless asymmetric dihydroxylation, epoxidation, a trans regioselective opening of 2,3-epoxy alcohol, Horner-Wadsworth-Emmons (HWE) olefination and amide coupling are the key steps. The amide alkaloids 1-3 are evaluated for their anticancer activity against colon (HT-29), breast (MCF-7) and lung (A-549) human cancer cell lines for the first time.
authors.affiliation: Organic Chemistry Division-II, Indian Institute of Chemical Technology, Hyderabad 500 607, India.
authors.forename: Ch
authors.initials: Ch
authors.lastname: Srinivas
authors.forename: Ch N S
authors.initials: ChN
authors.lastname: Sai Pavan Kumar
authors.forename: B
authors.initials: B
authors.lastname: China Raju
authors.forename: V
authors.initials: V
authors.lastname: Jayathirtha Rao
authors.forename: V G M
authors.initials: VG
authors.lastname: Naidu
authors.forename: S
authors.initials: S
authors.lastname: Ramakrishna
authors.forename: Prakash V
authors.initials: PV
authors.lastname: Diwan
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D045744:Cell Line, Tumor; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D026321:Piperaceae / Q000737:chemistry*; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D018517:Plant Roots / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D000577:Amides; D000970:Antineoplastic Agents; D010880:Piperidines