N-bromosuccinimide mediated decarboxylative sulfonylation of beta-keto acids with sodium sulfinates toward beta-keto sulfones: Evaluation of human carboxylesterase 1 activity

摘要

A N-bromosuccinimide (NBS) mediated decarboxylative sulfonylation of beta-keto acids with sodium sulfinates is developed. The transformation exhibits a broad substrate scope and good functional group tolerance. Preliminary mechanistic studies showed that this reaction is likely to proceed through a nucleophilic substitution of beta-keto acid with sulfonyl bromide pathway. All synthesized beta-keto sulfones were evaluated the inhibitory effect against human carboxylesterase 1 (CES1). This investigation offers an expedient strategy for efficient synthesis of beta-keto sulfones that are widely present in biologically active natural products and pharmaceutical agents. (C) 2018 Elsevier Ltd. All rights reserved.