Application In Synthesis of 2-(tert-Butyl)isothiazol-3(2H)-one 1,1-dioxide. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: 2-(tert-Butyl)isothiazol-3(2H)-one 1,1-dioxide, is researched, Molecular C7H11NO3S, CAS is 119639-24-6, about Isothiazolidinone heterocycles as inhibitors of protein tyrosine phosphatases: Synthesis and structure-activity relationships of a peptide scaffold. Author is Yue, Eddy W.; Wayland, Brian; Douty, Brent; Crawley, Matthew L.; McLaughlin, Erin; Takvorian, Amy; Wasserman, Zelda; Bower, Michael J.; Wei, Min; Li, Yanlong; Ala, Paul J.; Gonneville, Lucie; Wynn, Richard; Burn, Timothy C.; Liu, Phillip C. C.; Combs, Andrew P..
Oxo- and trioxo-substituted isothiazolidinylphenylalanines are prepared as tyrosine mimetics by Suzuki coupling reactions of chloroisothiazolidinones and chlorodioxoisothiazolidinones with N-Boc-4-borono-L-phenylalanine derivatives; the isothiazolidinylphenylalanines (with or without subsequent hydrogenation) are incorporated into dipeptides prepared as human protein tyrosine phosphatase 1B (PTP1B) inhibitors such as I. Of the compounds tested, I is the most potent inhibitor of PTP1B with an IC50 value of 40 nM; the corresponding mixture of isothiazolidinone diastereomers inhibits PTP1B with an IC50 value of 80 nM, and the separated (R)-isothiazolidinone diastereomer inhibits PTB1B with an IC50 value of 15.5 μM; the related dipeptides prepared inhibit PTP1B less potently than either I or the mixture of isothiazolidine diastereomers containing I. Crystal structures of a dioxothiazolidinone-substituted dipeptide and a dioxoisothiazolinone-substituted dipeptide bound to PTP1B are determined by X-ray crystallog.; the low energy conformation found by ab initio calculations for the saturated heterocycle more closely approaches the conformation obtained upon binding to PTP1B than that of the unsaturated heterocycle.
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Reference:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com