کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
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1374444 | 981919 | 2009 | 5 صفحه PDF | دانلود رایگان |
New topical anti-infectives comprised of N,N-dichloro-β,β-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 β-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 (H2O, pH 4–7, 0–20 mM acetate or phosphate buffer, 20–40 °C). This process produces β-ketosulfonic acids which function as substrates for chlorination by the N-chlorotaurines which leads to their further degradation.
The structure–stability relationship (SSR) of alkyl and cycloalkyl β-substitutions on N,N-dichlorotaurines reveals order-of-magnitude changes in their aqueous (pH 4–7, 20–40 °C) stabilities. Stieglitz rearrangement is one of the mechanisms of decomposition and produces β-ketosulfonic acids and chlorinated derivatives thereof.Figure optionsDownload as PowerPoint slide
Journal: Bioorganic & Medicinal Chemistry Letters - Volume 19, Issue 4, 15 February 2009, Pages 1110–1114