Synthesis and spectroscopic characterisation of a combinatorial library based on the fungal natural product 3-chloro-4-hydroxyphenylacetamide.
Parallel solution-phase chemistry has yielded a series of secondary amide analogues of the fungal natural product 3-chloro-4-hydroxyphenylacetamide. 3-Chloro-4-hydroxyphenylacetic acid was coupled to a variety of primary amines using 1-ethyl-3-(3'-dimethylamino- propyl)-carbodiimide hydrochloride. The desired products were obtained in good yield and high purity following rapid silica purification. All analogues were spectroscopically characterised using NMR, UV, IR and MS data. One compound displayed moderate cytotoxicity against the human melanoma and prostate cell lines, MM96L and DU145.
Davis
Rohan A
RA
Natural Product Discovery, Eskitis Institute for Cell and Molecular Therapies, Griffith University, Brisbane, QLD 4111, Australia. r.davis@griffith.edu.au
Pierens
Gregory K
GK
Parsons
Peter G
PG
D044482:Benzeneacetamides / Q000737:chemistry*; D001685:Biological Factors / Q000737:chemistry*; D020650:Combinatorial Chemistry Techniques; D005658:Fungi / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure
C521462:3-chloro-4-hydroxyphenylacetamide; D044482:Benzeneacetamides; D001685:Biological Factors