1,2,3,4-tetrahydroquinoline-based selective human neuronal nitric oxide synthase (nNOS) inhibitors: Lead optimization studies resulting in the identification of N-(1-(2-(methylamino)ethyl)-1,2,3,4-tetrahydroquinolin-6-yl) thiophene-2-carboximidamide as a preclinical development candidate

Journal of Medicinal Chemistry

Volumn 55, Issue 6, 2012, Pages 2882-2893

  Ramnauth, Jailall ^a   Renton, Paul ^a   Dove, Peter ^a   Annedi, Subhash C ^a   Speed, Joanne ^a   Silverman, Sarah ^a   Mladenova, Gabriela ^a   Maddaford, Shawn P ^a   Zinghini, Salvatore ^a   Rakhit, Suman ^a   Andrews, John ^a   Lee, David K H ^b   Zhang, Dongqin ^c   Porreca, Frank ^c  

^a NeurAxon Inc   (Canada)

^b NoAb BioDiscoveries Inc   (Canada)

^c UNIVERSITY OF ARIZONA COLLEGE OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 (6 BROMO 3,4 DIHYDROQUINOLIN 1(2H) YL) 2 (ETHYL(METHYL) AMINO)ETHANONE; 1 [6 BROMO 3,4 DIHYDROQUINOLIN 1 (2H) YL] 2 CHLOROETHANONE; 2 ((2 (6 BROMO 3,4 DIHYDROQUINOLIN 1(2H) YL)ETHYL)(METHYL)AMINO)ETHANOL; 2 (2 HYDROXYETHYLAMINO) 1 [6 NITRO 3,4 DIHYDROQUINOLIN 1(2H) YL]ETHANONE; 2 [6 BROMO 3,4 DIHYDROQUINOLIN 1(2H) YL N ETHYLETHAN AMINE; 6 BROMO 1 (2 CHLOROETHYL) 1,2,3,4 TETRAHYDROQUINOLINE; 6 BROMO 1 (2 IODOETHYL) 1,2,3,4 TETRAHYDROQUINOLINE; AMINO ACID DERIVATIVE; N (1 (PYRROLIDIN 3 YL) 1,2,3,4 TETRAHYDROQUINOLIN 6 YL) THIOPHENE 2 CARBOXIMIDAMIDE; N [1 (2 [ETHYL(METHYL)AMINO]ETHYL] 1,2,3,4 TETRAHYDROQUINOLIN 6 YL]THIOPHENE 2 CARBOXIMIDAMIDE; N [1 [2 (2 HYDROXYETHYLAMINO)ETHYL] 1,2,3,4 TETRAHYDROQUINOLINOLINE 6 YL]THIOPHENE 2 CARBOXIMIDAMIDE; N [1 [2 (ETHYLAMINO)ETHYL] 1,2,3,4 TETRAHYDROQUINOLIN 6 YL] THIOPHENE 2 CARBOXIMIDAMIDE; N [1 [2 (ISOPROPYLAMINO)ETHYL] 1,2,3,4 TETRAHYDROQUINOLIN 6 YL]THIOPHENE 2 CARBOXIMIDAMID; N [1 [2 (METHYLAMINO)ETHYL] 1,2,3,4 TETRAHYDROQUINOLIN 6 YL]THIOPHENE 2 CARBOXIMIDAMIDE; N [1 [2 [(2 HYDROXYETHYL)(METHYL)AMINO]ETHYL] 1,2,3,4 TETRAHYDROQUINOLIN 6 YL]THIOPHENE 2 CARBOXIMIDAMIDE; N [1 [3 (METHYLAMINO)PROPYL] 1,2,3,4 TETRAHYDROQUINOLIN 6 YL]THIOPHENE 2 CARBOXIMIDAMIDE; N [1 [3 2 (9HYDROXYETHYLAMINO)PROPYL] 1,2,3,4 TETRAHYDROQUINOLIN 6 YL]THIOPHENE 2 CARBOXIMIDAMIDE; N [2 [6 BROMO 3,4 DIHYDROQUINOLIN 1(2H) YL]ETHYL]PROPAN 2 AMINE; NEURONAL NITRIC OXIDE SYNTHASE; NITRIC OXIDE SYNTHASE INHIBITOR; PHENYL METHYL[2 [6 NITRO 3,4 DIHYDROQUINOLIN 1(2H) YL] ETHYL]CARBAMATE; PHENYL METHYL[3 (6 NITRO 3,4 DIHYDROQUINOLIN 1(2H) YL PROPYL]CARBAMATE; PHENYL METHYL[3 [6 (THIOPHENE 2 CARBOXIMIDAMIDO) 3,4 DIHYDROQUINOLIN 1(2H) YL]PROPYL]CARBAMATE; QUINOLINE DERIVATIVE; TERT BUTYL 2 (6 BROMO-3,4 DIHYDROQUINOLIN 1(2H) YL)ETHYL (ETHYL)CARBAMATE; TERT BUTYL 2 [6 BROMO 3,4 DIHYDROQUINOLIN 1(2H) YL)ETHY](ISOPROPYL)CARBAMATE; TERT BUTYL 2 HYDROXYETHYL(2 (6 NITRO 3,4 DIHYDROQUINOLIN 1(2H) YL) 2 OXOETHYL)CARBAMATE; TERT BUTYL 2 HYDROXYETHYL[3 [6 (THIOPHENE 2 CARBOXIMIDAMIDO) 3,4 DIHYDROQUINOLIN 1(2H) YL)PROPYL]CARBAMATE; TERT BUTYL 3 [6 (THIOPHENE 2 CARBOXIMIDAMIDO) 3,4 DIHYDROQUINOLIN 1(2H) YL]PYRROLIDINE 1 CARBOXYLATE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; CONTROLLED STUDY; DISEASE MODEL; DRUG ACTIVITY; DRUG BIOAVAILABILITY; DRUG DETERMINATION; DRUG SAFETY; HUMAN; HUMAN CELL; IC 50; MOLECULAR LIBRARY; NEUROPATHIC PAIN; NONHUMAN; PATCH CLAMP; PHYSICAL CHEMISTRY; RAT; REACTION OPTIMIZATION;

ADMINISTRATION, ORAL; ANALGESICS; ANIMALS; BIOLOGICAL AVAILABILITY; ETHER-A-GO-GO POTASSIUM CHANNELS; HIGH-THROUGHPUT SCREENING ASSAYS; HUMANS; NEURALGIA; NITRIC OXIDE SYNTHASE TYPE I; PATCH-CLAMP TECHNIQUES; QUINOLINES; RATS; SMALL MOLECULE LIBRARIES; STRUCTURE-ACTIVITY RELATIONSHIP; THIOPHENES;

EID: 84863376247     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm3000449     Document Type: Article

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