First stereoselective total synthesis and anticancer activity of new amide alkaloids of roots of pepper.
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.
Srinivas
Ch
Ch
Organic Chemistry Division-II, Indian Institute of Chemical Technology, Hyderabad 500 607, India.
Sai Pavan Kumar
Ch N S
ChN
China Raju
B
B
Jayathirtha Rao
V
V
Naidu
V G M
VG
Ramakrishna
S
S
Diwan
Prakash V
PV
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
D000470:Alkaloids; D000577:Amides; D000970:Antineoplastic Agents; D010880:Piperidines