Design and synthesis of novel 7-heterocycle-6-trifluoromethyl-3- oxoquinoxaline-2-carboxylic acids bearing a substituted phenyl group as superior AMPA receptor antagonists with good physicochemical properties

Bioorganic and Medicinal Chemistry

Volumn 14, Issue 3, 2006, Pages 776-792

  Takano, Yasuo ^a   Shiga, Futoshi ^a   Asano, Jun ^a   Hori, Wataru ^a   Fukuchi, Kazunori ^a   Anraku, Tsuyoshi ^a   Uno, Takashi ^a  

^a KYORIN PHARMACEUTICAL CO LTD   (Japan)

Author keywords

3 Oxoquinoxaline 2 carboxylic acid; Cerebral ischemia; Competitive AMPA receptor antagonist; Excitatory amino acid

Indexed keywords

3,4 DIHYDRO 3 OXO 6 TRIFLUOROMETHYL 7 [4 [(4 TRIFLUOROMETHYLPHENYLAMINO) CARBONYLOXYMETHYL]IMIDAZOL 1 YL]QUINOXALINE 2 CARBOXYLIC ACID; 3,4 DIHYDRO 3 OXO 7 (PYRROL 1 YL) 6 TRIFLUOROMETHYLQUINOXALINE 2 CARBOXYLIC ACID; 3,4 DIHYDRO 3 OXO 7 [3 [[(PHENYLAMINO)CARBONYL]AMINOMETHYL]PYRROL 1 YL] 6 TRIFLUOROMETHYLQUINOXALINE 2 CARBOXYLIC ACID; 3,4 DIHYDRO 3 OXO 7 [4 [(PHENYLAMINO)CARBONYLOXYMETHYL]IMIDAZOL 1 YL] 6 TRIFLUOROMETHYLQUINOXALINE 2 CARBOXYLIC ACID; 3,4 DIHYDRO 3 OXO 7 [4 [[(PHENYLAMINO)CARBONYL]AMINOMETHYL]IMIDAZOL 1 YL] 6 TRIFLUOROMETHYLQUINOXALINE 2 CARBOXYLIC ACID; 3,4 DIHYDRO 7 (4 IMIDAZOL 1 YL) 3 OXO 6 TRIFLUOROMETHYLQUINOXALINE 2 CARBOXYLIC ACID; 3,4 DIHYDRO 7 [4 [(4 METHOXYPHENYLAMINO)CARBONYLOXYMETHYL]IMIDAZOL 1 YL] 3 OXO 6 TRIFLUOROMETHYLQUINOXALINE 2 CARBOXYLIC ACID; 3,4 DIHYDRO 7 [4 [(4 METHYLPHENYLAMINO)CARBONYLOXYMETHYL]IMIDAZOL 1 YL] 3 OXO 6 TRIFLUOROMETHYLQUINOXALINE 2 CARBOXYLIC ACID; 3,4 DIHYDRO 7 [4 [[(4 METHOXYPHENYLAMINO)CARBONYL]AMINOMETHYL]IMIDAZOL 1 YL] 3 OXO 6 TRIFLUOROMETHYLQUINOXALINE 2 CARBOXYLIC ACID; 6 (1 IMIDAZOLYL) 7 NITRO 2,3 QUINOXALINEDIONE; 7 [3 [[(4 CARBOXYPHENYLAMINO)CARBONYL]AMINOMETHYL]PYRROL 1 YL] 3,4 DIHYDRO 3 OXO 6 TRIFLUOROMETHYLQUINOXALINE 2 CARBOXYLIC ACID; 7 [4 [(3 BROMOPHENYLAMINO)CARBONYLOXYMETHYL]IMIDAZOL 1 YL] 3,4 DIHYDRO 3 OXO 6 TRIFLUOROMETHYLQUINOXALINE 2 CARBOXYLIC ACID; 7 [4 [(3 CARBOXYPHENYLAMINO)CARBONYLOXYMETHYL]IMIDAZOL 1 YL] 3,4 DIHYDRO 3 OXO 6 TRIFLUOROMETHYLQUINOXALINE 2 CARBOXYLIC ACID; 7 [4 [(4 BROMOPHENYLAMINO)CARBONYLOXYMETHYL]IMIDAZOL 1 YL] 3,4 DIHYDRO 3 OXO 6 TRIFLUOROMETHYLQUINOXALINE 2 CARBOXYLIC ACID; 7 [4 [(4 CARBOXYPHENYLAMINO)CARBONYLOXYMETHYL]IMIDAZOL 1 YL] 3,4 DIHYDRO 3 OXO 6 TRIFLUOROMETHYLQUINOXALINE 2 CARBOXYLIC ACID; 7 [4 [[(3 CARBOXYMETHYLPHENYLAMINO)CARBONYL]AMINOMETHYL]IMIDAZOL 1 YL] 3,4 DIHYDRO 3 OXO 6 TRIFLUOROMETHYLQUINOXALINE 2 CARBOXYLIC ACID; 7 [4 [[(3 CARBOXYPHENYLAMINO)CARBONYL]AMINOMETHYL]IMIDAZOL 1 YL] 3,4 DIHYDRO 3 OXO 6 TRIFLUOROMETHYLQUINOXALINE 2 CARBOXYLIC ACID; 7 [4 [[(4 BROMOPHENYLAMINO)CARBONYL]AMINOMETHYL]IMIDAZOL 1 YL] 3,4 DIHYDRO 3 OXO 6 TRIFLUOROMETHYLQUINOXALINE 2 CARBOXYLIC ACID; 7 [4 [[(4 CARBOXYMETHYLPHENYLAMINO)CARBONYL]AMINOMETHYL]IMIDAZOL 1 YL] 3,4 DIHYDRO 3 OXO 6 TRIFLUOROMETHYLQUINOXALINE 2 CARBOXYLIC ACID; 7 [4 [[(4 CARBOXYPHENYLAMINO)CARBONYL]AMINOMETHYL]IMIDAZOL 1 YL] 3,4 DIHYDRO 3 OXO 6 TRIFLUOROMETHYLQUINOXALINE 2 CARBOXYLIC ACID; 7 [4 [[3 (CARBOXYMETHYL)PHENYLAMINO]CARBONYLOXYMETHYL]IMIDAZOL 1 YL] 3,4 DIHYDRO 3 OXO 6 TRIFLUOROMETHYLQUINOXALINE 2 CARBOXYLIC ACID; 7 [4 [[4 (CARBOXYMETHYL)PHENYLAMINO]CARBONYLOXYMETHYL]IMIDAZOL 3,4 DIHYDRO 3 OXO 6 TRIFLUOROMETHYL 1 YL]QUINOXALINE 2 CARBOXYLIC ACID; [1,2,3,4 TETRAHYDRO 7 (1H IMIDAZOL 1 YL) 6 NITRO 2,3 DIOXO 1 QUINOXALINYL]ACETIC ACID; AMPA RECEPTOR; AMPA RECEPTOR ANTAGONIST; FUNCTIONAL GROUP; GRA 293; KRP 199; PHENYL GROUP; QUINOXALINE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; AQUEOUS SOLUTION; ARTICLE; BRAIN ISCHEMIA; CONTROLLED STUDY; DRUG DESIGN; DRUG EFFECT; DRUG POTENCY; DRUG RECEPTOR BINDING; DRUG SELECTIVITY; DRUG SOLUBILITY; DRUG STABILITY; DRUG SYNTHESIS; IN VITRO STUDY; MALE; NEUROPROTECTION; NONHUMAN; PHYSICAL CHEMISTRY; RAT; RECEPTOR AFFINITY; STRUCTURE ACTIVITY RELATION;

ANIMALS; BRAIN ISCHEMIA; CEREBRAL CORTEX; CHEMISTRY, PHYSICAL; DRUG DESIGN; DRUG STABILITY; EVOKED POTENTIALS; MALE; MOLECULAR STRUCTURE; NEUROPROTECTIVE AGENTS; QUINOXALINES; RADIOLIGAND ASSAY; RATS; RATS, WISTAR; RECEPTORS, AMPA; SOLUBILITY;

ANIMALIA;

EID: 28844431546     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2005.08.060     Document Type: Article

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