Constrained (l-)-S-adenosyl-l-homocysteine (SAH) analogues as DNA methyltransferase inhibitors

…, AJ Petschner, J Rahil, N Beaulieu, F Gauthier…

Index: Isakovic, Ljubomir; Saavedra, Oscar M.; Llewellyn, David B.; Claridge, Stephen; Zhan, Lijie; Bernstein, Naomy; Vaisburg, Arkadii; Elowe, Nadine; Petschner, Andrea J.; Rahil, Jubrail; Beaulieu, Norman; Gauthier, France; MacLeod, A. Robert; Delorme, Daniel; Besterman, Jeffrey M.; Wahhab, Amal Bioorganic and Medicinal Chemistry Letters, 2009 , vol. 19, # 10 p. 2742 - 2746

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Citation Number: 29

Abstract

Potent SAH analogues with constrained homocysteine units have been designed and synthesized as inhibitors of human DNMT enzymes. The five membered (2S, 4S)-4- mercaptopyrrolidine-2-carboxylic acid, in 1a, was a good replacement for homocysteine, while the corresponding six-member counterpart was less active. Further optimization of 1a, changed the selectivity profile of these inhibitors. A Chloro substituent at the 2-position of ...

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