title: Stieglitz rearrangement of N,N-dichloro-beta,beta-disubstituted taurines under mild aqueous conditions.
abstract: 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 beta-ketosulfonic acids which function as substrates for chlorination by the N-chlorotaurines which leads to their further degradation.
authors.affiliation: NovaBay Pharmaceuticals, 5980 Horton St. Suite 550, Emeryville, CA 94608, USA. tshiau@novabaypharma.com
authors.forename: Timothy P
authors.initials: TP
authors.lastname: Shiau
authors.forename: Ashley
authors.initials: A
authors.lastname: Houchin
authors.forename: Satheesh
authors.initials: S
authors.lastname: Nair
authors.forename: Ping
authors.initials: P
authors.lastname: Xu
authors.forename: Eddy
authors.initials: E
authors.lastname: Low
authors.forename: Ramin Ron
authors.initials: RR
authors.lastname: Najafi
authors.forename: Rakesh
authors.initials: R
authors.lastname: Jain
mesh_terms: D020650:Combinatorial Chemistry Techniques; D006843:Hydrocarbons, Chlorinated / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D015394:Molecular Structure; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D013654:Taurine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D014867:Water / Q000737:chemistry
chemical_list: D006843:Hydrocarbons, Chlorinated; D014867:Water; D013654:Taurine