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 and their anti cancer activity is reported. The first stereoselective total synthesis of new natural amide alkaloids 1– 3 have been achieved from commercially available starting materials. Wittig olefination, Sharpless asy...

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Bibliographic Details
Published in:	Bioorganic & medicinal chemistry letters Vol. 19; no. 20; pp. 5915 - 5918
Main Authors:	Srinivas, Ch, Sai Pavan Kumar, Ch.N.S., China Raju, B., Jayathirtha Rao, V., Naidu, V.G.M., Ramakrishna, S., Diwan, Prakash V.
Format:	Journal Article
Language:	English
Published:	Amsterdam Elsevier Ltd 15-10-2009 Elsevier
Subjects:	Alkaloids - chemical synthesis Alkaloids - chemistry Alkaloids - pharmacology Amide alkaloids Amides - chemical synthesis Amides - chemistry Amides - pharmacology Anticancer activity Antineoplastic agents Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacology Biological and medical sciences Cell Line, Tumor Drug Screening Assays, Antitumor Epoxidation General aspects Humans HWE olefination Medical sciences Pharmacology. Drug treatments Piperaceae - chemistry Piperidines - chemical synthesis Piperidines - chemistry Piperidines - pharmacology Plant Roots - chemistry Sharpless asymmetric dihydroxylation Stereoisomerism Stereoselective synthesis Wittig olefination HWE olefination Amide alkaloids Wittig olefination Anticancer activity Epoxidation Stereoselective synthesis Sharpless asymmetric dihydroxylation Antineoplastic agent Osmium Complexes Epimer Lung Cytotoxicity Alkanal Stereoselectivity Alkaloid Dicotyledones Angiospermae Vinylic compound Piperidine derivatives Asymmetric reaction Colon Mammary gland Chemical synthesis Tumor cell Below ground plant part Human Wittig reaction Root Aliphatic compound Olefination Piperaceae Transition metal Complexes Aldehyde In vitro Biological activity Total synthesis Cell line Sharpless dihydroxylation Plant origin Carboxamide Platinoid Complexes Spermatophyta Piper Glycol
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Summary:	The first stereoselective total synthesis of new natural amide alkaloids 1– 3 and their anti cancer activity is reported. 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.
Bibliography:	ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	0960-894X 1464-3405
DOI:	10.1016/j.bmcl.2009.08.056