Stieglitz rearrangement of N, N-dichloro-β,β-disubstituted taurines under mild aqueous conditions

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 chlo...

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Veröffentlicht in:Bioorganic & medicinal chemistry letters 2009-02, Vol.19 (4), p.1110-1114
Hauptverfasser: Shiau, Timothy P., Houchin, Ashley, Nair, Satheesh, Xu, Ping, Low, Eddy, Najafi, Ramin (Ron), Jain, Rakesh
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container_end_page 1114
container_issue 4
container_start_page 1110
container_title Bioorganic & medicinal chemistry letters
container_volume 19
creator Shiau, Timothy P.
Houchin, Ashley
Nair, Satheesh
Xu, Ping
Low, Eddy
Najafi, Ramin (Ron)
Jain, Rakesh
description 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. 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 (H 2O, 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.
doi_str_mv 10.1016/j.bmcl.2008.12.109
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subjects Antimicrobial
Chloroamines
Chlorotaurine
Combinatorial Chemistry Techniques
Dichloroamines
Hydrocarbons, Chlorinated - chemical synthesis
Hydrocarbons, Chlorinated - chemistry
Hydrocarbons, Chlorinated - pharmacology
Molecular Structure
Rearrangement
Stereoisomerism
Stieglitz
Structure-Activity Relationship
Sulfinimine addition
Taurine
Taurine - analogs & derivatives
Taurine - chemical synthesis
Taurine - chemistry
Taurine - pharmacology
Water - chemistry
title Stieglitz rearrangement of N, N-dichloro-β,β-disubstituted taurines under mild aqueous conditions
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