Discovery of a benzimidazole series of ADAMTS-5 (aggrecanase-2) inhibitors by scaffold hopping

European Journal of Medicinal Chemistry

Volumn 71, Issue , 2014, Pages 250-258

  Sogame, Shinya ^a   Suenaga, Yoshihito ^a   Atobe, Masakazu ^a   Kawanishi, Masashi ^a   Tanaka, Eiichi ^a   Miyoshi, Shiro ^a  

^a ASAHI KASEI PHARMA CORPORATION   (Japan)

Author keywords

ADAMTS 5; Benzimidazole; Inhibitor; Osteoarthritis; Thiazolidin 4 one

Indexed keywords

2 (1H BENZO[D]IMIDAZOL 2 YL) N METHYLETHANETHIOAMIDE; 2 (BENZO[D]OXAZOL 2 YLMETHYLENE)THIAZOLIDIN 4 ONE; 2 (BENZO[D]THIAZOL 2 YLMETHYLENE)THIAZOLIDIN 4 ONE; 2 (THIOPHEN 2 YLMETHYLENE)THIAZOLIDIN 4 ONE; 2 [(1 METHYL 1H BENZO[D]IMIDAZOL 2 YL)METHYLENE]THIAZOLIDIN 4 ONE; 2 [(1H BENZO[D]IMIDAZOL 2 YL)METHYLENE] 3 METHYLTHIAZOLIDIN 4 ONE; 2 [(1H BENZO[D]IMIDAZOL 2 YL)METHYLENE] 5 (2 HYDROXY ETHYL)THIAZOLIDIN 4 ONE; 2 [(1H BENZO[D]IMIDAZOL 2 YL)METHYLENE] 5 BUTYLTHIAZO LIDIN 4 ONE; 2 [(1H BENZO[D]IMIDAZOL 2 YL)METHYLENE] 5 ETHYLTHIAZO LIDIN 4 ONE; 2 [(1H BENZO[D]IMIDAZOL 2 YL)METHYLENE] 5 METHYLTHIA ZOLIDIN 4 ONE; 2 [(1H BENZO[D]IMIDAZOL 2 YL)METHYLENE] 5 PROPYLTHIA ZOLIDIN 4 ONE; 2 [(1H IMIDAZOL 5 YL)METHYLENE]THIAZOLIDIN 4 ONE; 2 [(1H NAPHTHO[2,3 D]IMIDAZOL 2 YL)METHYLENE]THIAZOLIDIN 4 ONE; 2 [(4 HYDROXYTHIAZOL 2 YL)METHYLENE]THIAZOLIDIN 4 ONE; 2 [(4,5 DIHYDRONAPHTHO[1,2 D]THIAZOL 2 YL)METHYLENE]THIAZOLIDIN 4 ONE; 2 [(4H THIOCHROMENO[4,3 D]THIAZOL 2 YL)METHYLENE]THIAZOLIDIN 4 ONE; 2 [(5,6 DIMETHYL 1H BENZO[D]IMIDAZOL 2 YL)METHYLENE] 5 PROPYLTHIAZOLIDIN 4 ONE; 2 [(5,6 DIMETHYL 1H BENZO[D]IMIDAZOL 2 YL)METHYLENE]THIAZOLIDIN 4 ONE; 2 [(6 FLUORO 1H BENZO[D]IMIDAZOL 2 YL)METHYLENE] 5 PROPYLTHIAZOLIDIN 4 ONE; 2 [(6 METHYL 1H BENZO[D]IMIDAZOL 2 YL)METHYLENE] 5 PROPYLTHIAZOLIDIN 4 ONE; 2 [(6 METHYL 1H BENZO[D]IMIDAZOL 2 YL)METHYLENE]THIAZOLIDIN 4 ONE; 2 [(7 METHYL 1H BENZO[D]IMIDAZOL 2 YL)METHYLENE] 5 PROPYLTHIAZOLIDIN 4 ONE; 2 [(7 METHYL 1H BENZO[D]IMIDAZOL 2 YL)METHYLENE]THIAZOLIDIN 4 ONE; 2 [(8H INDENO[1,2 D]THIAZOL 2 YL)METHYLENE]THIAZOLIDIN 4 ONE; 2 [[4 (PYRIDIN 2 YL)THIAZOL 2 YL]METHYLENE]THIAZOLIDIN 4 ONE; 5 PROPYL 2 [[6 (TRIFLUOROMETHYL) 1H BENZO[D]IMIDAZOL 2 YL]METHYLENE] THIAZOLIDIN 4 ONE; AGGRECANASE 2; BENZIMIDAZOLE DERIVATIVE; METALLOPROTEINASE INHIBITOR; UNCLASSIFIED DRUG; UNINDEXED DRUG; ADAM PROTEIN; ADAMTS5 PROTEIN, HUMAN; BENZIMIDAZOLE; INHIBITOR;

ARTICLE; DRUG SYNTHESIS; MOLECULAR WEIGHT; PERMEABILITY; PH; PHYSICAL CHEMISTRY; PROTON NUCLEAR MAGNETIC RESONANCE; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ADAMTS-5; CHEMISTRY; DRUG ANTAGONISM; DRUG DESIGN; HUMAN; METABOLISM; OSTEOARTHRITIS; STRUCTURE ACTIVITY RELATION; THIAZOLIDIN-4-ONE;

ADAMTS-5; BENZIMIDAZOLE; INHIBITOR; OSTEOARTHRITIS; THIAZOLIDIN-4-ONE;

ADAM PROTEINS; BENZIMIDAZOLES; DRUG DESIGN; HUMANS; OSTEOARTHRITIS; PERMEABILITY; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84890114835     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2013.10.075     Document Type: Article

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