beta-aminoacyl-thiazolidine-2da
IC(50) value of 1 nM, and selective over DPP-2, DPP-8, and DPP-9. Stable, and showed no CYP inhibition, hERG binding or cytotoxicity. Compound 2db, an ester prodrug of 2da, showed good in vivo DPP-IV inhibition after oral administration in rat and dog models.
General
Type : Trifluoro,Sulfur Compound,Thiazolidine
Chemical_Nomenclature : (2R)-2-[4-[[[3-[(3R)-3-amino-4-(2,4,5-trifluorophenyl)butanoyl]-1,3-thiazolidine-2-carbonyl]amino]methyl]anilino]-3-methylbutanoic acid
Canonical SMILES : CC(C)C(C(=O)O)NC1=CC=C(C=C1)CNC(=O)C2N(CCS2)C(=O)CC(CC3=CC(=C(C=C3F)F)F)N
InChI : InChI=1S\/C26H31F3N4O4S\/c1-14(2)23(26(36)37)32-18-5-3-15(4-6-18)13-31-24(35)25-33(7-8-38-25)22(34)11-17(30)9-16-10-20(28)21(29)12-19(16)27\/h3-6,10,12,14,17,23,25,32H,7-9,11,13,30H2,1-2H3,(H,31,35)(H,36,37)\/t17-,23-,25?\/m1\/s1
InChIKey : ZUNWVBNRQTWJFD-DELLSAQKSA-N
Other name(s) : N-(4-{[({(2r)-3-[(3r)-3-Amino-4-(2,4,5-Trifluorophenyl)butanoyl]-1,3-Thiazolidin-2-Yl}carbonyl)amino]methyl}phenyl)-D-Valine,AZV,2DA
MW : 552.61
Formula : C26H31F3N4O4S
CAS_number :
PubChem : 50919286
UniChem : ZUNWVBNRQTWJFD-DELLSAQKSA-N
IUPHAR :
Wikipedia :
Target
Families : beta-aminoacyl-thiazolidine-2da ligand of proteins in family: DPP4N_Peptidase_S9
Stucture : 3Q8W A b-aminoacyl containing thiazolidine derivative and DPPIV complex
Protein : human-DPP4
References (1)
| Title : Discovery of beta-aminoacyl containing thiazolidine derivatives as potent and selective dipeptidyl peptidase IV inhibitors - Park_2011_Bioorg.Med.Chem.Lett_21_1366 |
| Author(s) : Park WS , Kang SK , Jun MA , Shin MS , Kim KY , Rhee SD , Bae MA , Kim MS , Kim KR , Kang NS , Yoo SE , Lee JO , Song DH , Silinski P , Schneider SE , Ahn JH , Kim SS |
| Ref : Bioorganic & Medicinal Chemistry Lett , 21 :1366 , 2011 |
| Abstract : Park_2011_Bioorg.Med.Chem.Lett_21_1366 |
| ESTHER : Park_2011_Bioorg.Med.Chem.Lett_21_1366 |
| PubMedSearch : Park_2011_Bioorg.Med.Chem.Lett_21_1366 |
| PubMedID: 21306895 |
| Gene_locus related to this paper: human-DPP4 |