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Design, synthesis and spectroscopic characterisation of a focused library based on the polyandrocarpamine natural product scaffold
Author(s) -
Baron Paul S.,
Neve Juliette E.,
Camp David,
Suraweera Lekha,
Lam Ann,
Lai John,
Jovanovic Lidija,
Nelson Colleen,
Davis Rohan A.
Publication year - 2013
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.3958
Subject(s) - chemistry , natural product , lncap , aldol condensation , combinatorial chemistry , cancer cell lines , in silico , cytotoxicity , aldol reaction , organic chemistry , in vitro , prostate cancer , cancer cell , biochemistry , cancer , catalysis , medicine , gene
A focused library based on the marine natural products polyandrocarpamines A ( 1 ) and B ( 2 ) has been designed and synthesised using parallel solution‐phase chemistry. In silico physicochemical property calculations were performed on synthetic candidates in order to optimise the library for drug discovery and chemical biology. A library of ten 2‐aminoimidazolone products ( 3–12 ) was prepared by coupling glycocyamidine and a variety of aldehydes using a one‐step stereoselective aldol condensation reaction under microwave conditions. All analogues were characterised by NMR, UV, IR and MS. The library was evaluated for cytotoxicity towards the prostate cancer cell lines, LNCaP, PC‐3 and 22Rv1. Copyright © 2013 John Wiley & Sons, Ltd.