期刊
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
卷 19, 期 4, 页码 1110-1114出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmcl.2008.12.109
关键词
Taurine; Chlorotaurine; Chloroamines; Dichloroamines; Stieglitz; Rearrangement; Antimicrobial; Sulfinimine addition
资金
- Alcon Laboratories
New topical anti-infectives comprised of N,N-dichloro-beta,beta-disubstituted taurines [Tetrahedron Lett. 2008, 49, 2193; Biorg. Med. Chem. Lett. 2009, 19, 196] have been examined for structure-stability relationships (SSR) based upon various alkyl, heteroalkyl and cycloalkyl beta-substitutions. These substitutions affect order-of-magnitude changes in the aqueous stability of these N,N-dichloroamines which can undergo Stieglitz rearrangement of alkyl groups under extremely mild conditions (H(2)O, pH 4-7, 0-20 mM acetate or phosphate buffer, 20-40 degrees C). This process produces b-ketosulfonic acids which function as substrates for chlorination by the N-chlorotaurines which leads to their further degradation. (C) 2009 Elsevier Ltd. All rights reserved.
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