Isothiazolidinone heterocycles as inhibitors of protein tyrosine phosphatases: Synthesis and structure-activity relationships of a peptide scaffold

Bioorganic and Medicinal Chemistry

Volumn 14, Issue 17, 2006, Pages 5833-5849

  Yue, Eddy W ^a   Wayland, Brian ^a   Douty, Brent ^a   Crawley, Matthew L ^a   McLaughlin, Erin ^a   Takvorian, Amy ^a   Wasserman, Zelda ^a   Bower, Michael J ^a   Wei, Min ^a   Li, Yanlong ^a   Ala, Paul J ^a   Gonneville, Lucie ^a   Wynn, Richard ^a   Burn, Timothy C ^a   Liu, Phillip C C ^a   Combs, Andrew P ^a  

^a Experimental Station   (United States)

Author keywords

Isothiazolidinone heterocycle; Phosphatase inhibitors; Phosphotyrosine mimetics; Protein tyrosine phosphatase 1B

Indexed keywords

2 (ACETYLAMINO) 3 [4 (1,1 DIOXIDO 3 OXOISOTHIAZOLIDIN 5 YL)PHENYL]PROPANAMIDE; 2 AMINO 3 [4 (1,1 DIOXIDO 3 OXOISOTHIAZOLIDIN 5 YL)PHENYL]PROPANAMIDE TRIFLUOROACETATE; 2 AMINO N [2 AMINO 1 [4 (1,1 DIOXIDO 3 OXOISOTHIAZOLIDIN 5 YL)BENZYL] 2 OXOETHYL] 3 PHENYLPROPANAMIDE TRIFLUOROACETATE; 3 [4 (1,1 DIOXIDO 3 OXO 2,3 DIHYDROISOTHIAZOL 4 YL)PHENYL] 2 [[2[[(4 METHOXYPHENYL)ACETYL]AMINO] 3 PHENYLPROPANOYL]AMINO] N PENTYLPROPANAMIDE; 3 [4 (1,1 DIOXIDO 3 OXO 2,3 DIHYDROISOTHIAZOL 5 YL)PHENYL] 2 [[2[[(4 METHOXYPHENYL)ACETYL]AMINO] 3 PHENYLPROPANOYL]AMINO] N PENTYLPROPANAMIDE; ISOTHIAZOLIDINONE DERIVATIVE; N [(4 METHOXYPHENYL)ACETYL]PHENYLALANYL 4 (1,1 DIOXIDO 4 OXO 1,2,5 THIADIAZOLIDIN 2 YL) N PENTYLPROPANAMIDE; N [2 [[2 AMINO 1 [ (1,1 DIOXIDO 3 OXO 2,3 DIHYDROISOTHIAZOL 5 YL)BENZYL] 2 OXOETHYL]AMINO] 1 BENZYL 2 OXOETHYL]BENZAMIDE; N [2 [[2 AMINO 1 [4 (1,1 DIOXIDO 3 OXOISOTHIAZOLIDIN 5 YL)BENZYL] 2 OXOETHYL]AMINO] 1 BENZYL 2 OXOETHYL]BENZAMIDE; N [2 AMINO 1 [4 (1,1 DIOXIDO 3 OXO 2,3 DIHYDROISOTHIAZOL 5 YL)1 BENZYL] 2 OXOETHYL] 3 PHENYL 2 [(PHENYLACETYL)AMINO]PROPANAMIDE; N [2 AMINO 1 [4 (1,1 DIOXIDO 3 OXO 2,3 DIHYDROISOTHIAZOL 5 YL)BENZYL] 2 OXOETHYL] 2 [[(4 HYDROXYPHENYL)ACETYL]AMINO] 3 PHENYLPROPANAMIDE; N [2 AMINO 1 [4 (1,1 DIOXIDO 3 OXO 2,3 DIHYDROISOTHIAZOL 5 YL)BENZYL] 2 OXOETHYL] 2 [[(4 METHOXYPHENYL)ACETYL]AMINO] 3 PHENYLPROPANAMIDE; N [2 AMINO 1 [4 (1,1 DIOXIDO 3 OXO 2,3 DIHYDROISOTHIAZOL 5 YL)BENZYL] 2 OXOETHYL] 3 PHENYL 2 [(3 PHENYLPROPANOYL)AMINO]PROPANAMIDE; N [2 AMINO 1 [4 (1,1 DIOXIDO 3 OXO 2,3 DIHYDROISOTHIAZOL 5 YL)BENZYL] 2 OXOETHYL] 3 PHENYL 2 [[(4 (TRIFLUOROMETHYL)PHENYL]ACETYL]AMINO]PROPANAMIDE; N [2 AMINO 1 [4 (1,1 DIOXIDO 3 OXOISOTHIAZOLIDIN 5 YL)BENZYL] 2 OXOETHYL] 2 [[(4 HYDROXYPHENYL)ACETYL]AMINO] 3 PHENYLPROPANAMIDE; N [2 AMINO 1 [4 (1,1 DIOXIDO 3 OXOISOTHIAZOLIDIN 5 YL)BENZYL] 2 OXOETHYL] 2 [[(4 METHOXYPHENYL)ACETYL]AMINO] 3 PHENYLPROPANAMIDE; N [2 AMINO 1 [4 (1,1 DIOXIDO 3 OXOISOTHIAZOLIDIN 5 YL)BENZYL] 2 OXOETHYL] 3 PHENYL 2 [(3 PHENYLPROPANOYL)AMINO]PROPANAMIDE; N [2 AMINO 1 [4 (1,1 DIOXIDO 3 OXOISOTHIAZOLIDIN 5 YL)BENZYL] 2 OXOETHYL] 3 PHENYL 2 [(PHENYLACETYL)AMINO]PROPANAMIDE; N [2 AMINO 1 [4 (1,1 DIOXIDO 3 OXOISOTHIAZOLIDIN 5 YL)BENZYL] 2 OXOETHYL] 3 PHENYL 2 [[[(4 (TRIFLUOROMETHYL)PHENYL]ACETYL]AMINO]PROPANAMIDE; PEPTIDE DERIVATIVE; PROTEIN TYROSINE PHOSPHATASE INHIBITOR; TERT BUTYL [2 AMINO 1 [4 (1,1 DIOXIDO 3 OXOISOTHIAZOLIDIN 5 YL)BENZYL] 2 OXOETHYL]CARBAMATE; UNCLASSIFIED DRUG;

AB INITIO CALCULATION; ARTICLE; BINDING AFFINITY; COMPARATIVE STUDY; CONFORMATION; CRYSTAL STRUCTURE; DRUG DESIGN; DRUG SYNTHESIS; ENERGY; STRUCTURE ACTIVITY RELATION; SUZUKI REACTION; X RAY CRYSTALLOGRAPHY;

ESCHERICHIA COLI; HUMANS; INTRACELLULAR SIGNALING PEPTIDES AND PROTEINS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PEPTIDES; PROTEIN-TYROSINE-PHOSPHATASE; SHP1 PROTEIN TYROSINE PHOSPHATASE; STRUCTURE-ACTIVITY RELATIONSHIP; THIAZOLES;

EID: 33746036019     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2006.05.032     Document Type: Article

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