Identification of 3-aminomethyl-1,2-dihydro-4-phenyl-1-isoquinolones: A new class of potent, selective, and orally active non-peptide dipeptidyl peptidase IV inhibitors that form a unique interaction with Lys554

Bioorganic and Medicinal Chemistry

Volumn 19, Issue 16, 2011, Pages 4953-4970

  Banno, Yoshihiro ^a   Miyamoto, Yasufumi ^a   Sasaki, Mitsuru ^a   Oi, Satoru ^a   Asakawa, Tomoko ^a   Kataoka, Osamu ^a   Takeuchi, Koji ^a   Suzuki, Nobuhiro ^a   Ikedo, Koji ^a   Kosaka, Takuo ^a   Tsubotani, Shigetoshi ^a   Tani, Akiyoshi ^a   Funami, Miyuki ^a   Tawada, Michiko ^a   Yamamoto, Yoshio ^a   Aertgeerts, Kathleen ^b   Yano, Jason ^b   Maezaki, Hironobu ^a  

^a TAKEDA PHARMACEUTICAL COMPANY LIMITED   (Japan)

^b Takeda San Diego Inc   (United States)

Author keywords

Anti diabetic effects; Dipeptidyl peptidase IV (DPP 4); Isoquinolone

Indexed keywords

2 [[3 (AMINOMETHYL) 2 (2 METHYLPROPYL) 1 OXO 4 PHENYL 1,2 DIHYDROISOQUINOLIN 6 YL]OXY]ACETAMIDE; 2 BUTYL 6 CHLORO 1 OXO 4 PHENYL 1,2 DIHYDROISOQUINOLINE 3 CARBOXYLIC ACID; 3 [3 (AMINOMETHYL) 2 (2 METHYLPROPYL) 1 OXO 4 PHENYL 1,2 DIHYDROISOQUINOLIN 6 YL]PROP 2 ENAMIDE; 3 AMINOMETHYL 1,2 DIHYDRO 4 PHENYL 1 ISOQUINOLONE DERIVATIVE; 4 CHLORO 2 (PHENYLCARBONYL)BENZOIC ACID; 4 FLUORO 2 (PHENYLCARBONYL)BENZOIC ACID; 6 BROMO 1 OXO 4 PHENYL 1H ISOCHROMENE 3 CARBOXYLIC ACID; 6 BROMO 2 (2 METHYLPROPYL) 1 OXO 4 PHENYL 1,2 DIHYDROISOQUINOLINE 3 CARBOXYLIC ACID; 6 CHLORO 1 OXO 2 PENTYL 4 PHENYL 1,2 DIHYDROISOQUINOLINE 3 CARBOXYLIC ACID; 6 CHLORO 1 OXO 4 PHENYL 1,2 DIHYDROISOQUINOLINE 3 CARBOXYLIC ACID; 6 CHLORO 1 OXO 4 PHENYL 1H ISOCHROMENE 3 CARBOXYLIC ACID; 6 CHLORO 2 (2 METHYLPROPYL) 1 OXO 4 PHENYL 1,2 DIHYDROISOQUINOLINE 3 CARBOXYLIC ACID; 6 CHLORO 2 (2,2 DIMETHYLPROPYL) 1 OXO 4 PHENYL 1,2 DIHYDROISOQUINOLINE 3 CARBOXYLIC ACID; 6 CHLORO 2 ETHYL 1 OXO 4 PHENYL 1,2 DIHYDROISOQUINOLINE 3 CARBOXYLIC ACID; 6 CHLORO 2 METHYL 1 OXO 4 PHENYL 1,2 DIHYDROISOQUINOLINE 3 CARBOXYLIC ACID; 6 FLUORO 1 OXO 4 PHENYL 1H ISOCHROMENE 3 CARBOXYLIC ACID; 6 FLUORO 2 (2 METHYLPROPYL) 1 OXO 4 PHENYL 1,2 DIHYDROISOQUINOLINE 3 CARBOXYLIC ACID; CYTOSOL AMINOPEPTIDASE; DIPEPTIDYL PEPTIDASE; DIPEPTIDYL PEPTIDASE 2; DIPEPTIDYL PEPTIDASE I; DIPEPTIDYL PEPTIDASE IV; DIPEPTIDYL PEPTIDASE IV INHIBITOR; GLUCOSE; INSULIN; LYSINE; PHENYL GROUP; PROLINE IMINOPEPTIDASE; PROLYL ENDOPEPTIDASE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ALKOXYCARBONYLATION; ALKYLATION; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; BENZYLATION; BINDING KINETICS; CHEMICAL MODIFICATION; CHLORINATION; CONTROLLED STUDY; CYCLIZATION; DISEASE MODEL; DRUG BINDING SITE; DRUG DOSE COMPARISON; DRUG EFFICACY; DRUG POTENCY; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; FEMALE; GLUCOSE BLOOD LEVEL; HUMAN; HYDROGEN BOND; HYDROLYSIS; HYDROPHILICITY; IC 50; INSULIN BLOOD LEVEL; METHANESULFONYLATION; METHOXYCARBONYLATION; METHYLATION; MOLECULAR INTERACTION; NON INSULIN DEPENDENT DIABETES MELLITUS; NONHUMAN; ORAL GLUCOSE TOLERANCE TEST; RAT; RING OPENING; SAPONIFICATION; STRUCTURE ACTIVITY RELATION; X RAY CRYSTALLOGRAPHY;

ADMINISTRATION, ORAL; ANIMALS; BLOOD GLUCOSE; CACO-2 CELLS; DIABETES MELLITUS, TYPE 2; DIPEPTIDYL PEPTIDASE 4; DIPEPTIDYL-PEPTIDASE IV INHIBITORS; DIPEPTIDYL-PEPTIDASES AND TRIPEPTIDYL-PEPTIDASES; DRUG DESIGN; FEMALE; GLUCOSE TOLERANCE TEST; HUMANS; HYPOGLYCEMIC AGENTS; ISOQUINOLINES; MOLECULAR TARGETED THERAPY; PEPTIDES; QUINOLONES; RATS; RATS, WISTAR; STRUCTURE-ACTIVITY RELATIONSHIP;

RATTUS;

EID: 79961165720     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2011.06.059     Document Type: Article

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