Discovery and biological evaluation of tetrahydrothieno[2,3-c]pyridine derivatives as selective metabotropic glutamate receptor 1 antagonists for the potential treatment of neuropathic pain

European Journal of Medicinal Chemistry

Volumn 97, Issue , 2015, Pages 245-258

  Nam, Mina ^a,b   Kim, TaeHun ^a,c   Kwak, Jinsook ^a,d   Seo, Seon Hee ^a   Ko, Min Kyung ^a   Lim, Eun Jeong ^a   Min, Sun Joon ^a   Cho, Yong Seo ^a   Keum, Gyochang ^a   Baek, Du Jong ^b   Lee, Jiyoun ^e   Pae, Ae Nim ^a,c  

^a Korea Institute of Science and Technology   (South Korea)

^b Sangmyung University   (South Korea)

^c University of Science and Technology (UST)   (South Korea)

^d Sogang University   (South Korea)

^e Sungshin Women's University   (South Korea)

Author keywords

Metabotropic glutamate receptor; mGluR1 antagonist; Neuropathic pain; Thiophene derivatives

Indexed keywords

2 (BENZYLAMINO) 6 (1H PYRAZOLE 5 CARBONYL) 4,5,6,7 TETRAHYDROTHIENO[2,3 C]PYRIDINE 3 CARBONITRILE; 2 (BENZYLAMINO) 6 (3 FLUOROBENZOYL) 4,5,6,7 TETRAHYDROTHIENO[2,3 C]PYRIDINE 3 CARBONITRILE; 2 (BENZYLAMINO) 6 (3 ISOPROPYL 1H PYRAZOLE 5 CARBONYL) 4,5,6,7 TETRAHYDROTHIENO[2,3 C]PYRIDINE 3 CARBONITRILE; 2 (BENZYLAMINO) 6 (3 METHYL 1H PYRAZOLE 5 CARBONYL) 4,5,6,7 TETRAHYDROTHIENO[2,3 C]PYRIDINE 3 CARBONITRILE; 2 (BENZYLAMINO) 6 (3 METHYLBENZOYL) 4,5,6,7 TETRAHYDROTHIENO[2,3 C]PYRIDINE 3 CARBONITRILE; 2 (BENZYLAMINO) 6 (4 FLUOROBENZOYL) 4,5,6,7 TETRAHYDROTHIENO[2,3 C]PYRIDINE 3 CARBONITRILE; 2 (BENZYLAMINO) 6 (6 FLUORONICOTINOYL) 4,5,6,7 TETRAHYDROTHIENO[2,3 C]PYRIDINE 3 CARBONITRILE; 2 [(4 CHLOROBENZYL)AMINO] 6 (3 ISOPROPYL 1H PYRAZOLE 5 CARBONYL) 4,5,6,7 TETRAHYDROTHIENO[2,3 C]PYRIDINE 3 CARBONITRILE; 2 [(4 CHLOROBENZYL)AMINO] 6 (3 METHYL 1H PYRAZOLE 5 CARBONYL) 4,5,6,7 TETRAHYDROTHIENO[2,3 C]PYRIDINE 3 CARBONITRILE; 2 [(4 FLUOROBENZYL)AMINO] 6 (1H PYRAZOLE 5 CARBONYL) 4,5,6,7 TETRAHYDROTHIENO[2,3 C]PYRIDINE 3 CARBONITRILE; 2 [(4 FLUOROBENZYL)AMINO] 6 (3 ISOPROPYL 1H PYRAZOLE 5 CARBONYL) 4,5,6,7 TETRAHYDROTHIENO[2,3 C]PYRIDINE 3 CARBONITRILE; 2 [(4 FLUOROBENZYL)AMINO] 6 (3 METHYL 1H PYRAZOLE 5 CARBONYL) 4,5,6,7 TETRAHYDROTHIENO[2,3 C]PYRIDINE 3 CARBONITRILE; 4 CHLORO N [3 CYANO 6 (3 ISOPROPYL 1H PYRAZOLE 5 CARBONYL) 4,5,6,7 TETRAHYDROTHIENO[2,3 C]PYRIDIN 2 YL]BENZAMIDE; 4 CHLORO N [3 CYANO 6 (3 METHYL 1H PYRAZOLE 5 CARBONYL) 4,5,6,7 TETRAHYDROTHIENO[2,3 C]PYRIDIN 2 YL]BENZAMIDE; 4 FLUORO N [3 CYANO 6 (3 ISOPROPYL 1H PYRAZOLE 5 CARBONYL) 4,5,6,7 TETRAHYDROTHIENO[2,3 C]PYRIDIN 2 YL]BENZAMIDE; 4 FLUORO N [3 CYANO 6 (3 METHYL 1H PYRAZOLE 5 CARBONYL) 4,5,6,7 TETRAHYDROTHIENO[2,3 C]PYRIDIN 2 YL]BENZAMIDE; 4 METHOXY N [3 CYANO 6 (3 ISOPROPYL 1H PYRAZOLE 5 CARBONYL) 4,5,6,7 TETRAHYDROTHIENO[2,3 C]PYRIDIN 2 YL]BENZAMIDE; 4 METHOXY N [3 CYANO 6 (3 METHYL 1H PYRAZOLE 5 CARBONYL) 4,5,6,7 TETRAHYDROTHIENO[2,3 C]PYRIDIN 2 YL]BENZAMIDE; 6 (4 FLUOROBENZOYL) 2 [(4 FLUOROBENZYL)AMINO] 4,5,6,7 TETRAHYDROTHIENO[2,3 C]PYRIDINE 3 CARBONITRILE; 6 BENZOYL 2 (BENZYLAMINO) 4,5,6,7 TETRAHYDROTHIENO[2,3 C]PYRIDINE 3 CARBONITRILE; 6 BENZOYL 2 [(4 FLUOROBENZYL)AMINO] 4,5,6,7 TETRAHYDROTHIENO[2,3 C]PYRIDINE 3 CARBONITRILE; ANALGESIC AGENT; GABAPENTIN; METABOTROPIC RECEPTOR 1; METABOTROPIC RECEPTOR ANTAGONIST; N [3 CYANO 6 (3 ISOPROPYL 1H PYRAZOLE 5 CARBONYL) 4,5,6,7 TETRAHYDROTHIENO[2,3 C]PYRIDIN 2 YL]BENZAMIDE; N [3 CYANO 6 (3 METHYL 1H PYRAZOLE 5 CARBONYL) 4,5,6,7 TETRAHYDROTHIENO[2,3 C]PYRIDIN 2 YL]BENZAMIDE; TETRAHYDROTHIENO[2,3 C]PYRIDINE DERIVATIVE; THIENOPYRIDINE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG; 2-(BENZYLAMINO)-6-(3-METHYL-1H-PYRAZOLE-5-CARBONYL)-4,5,6,7-TETRAHYDROTHIENO(2,3-C)PYRIDINE-3-CARBONITRILE; 2-(BENZYLAMINO)-6-(4-FLUOROBENZOYL)-4,5,6,7-TETRAHYDROTHIENO(2,3-C)PYRIDINE-3-CARBONITRILE; METABOTROPIC GLUTAMATE RECEPTOR TYPE 1; METABOTROPIC RECEPTOR; NITRILE; PYRIDINE; PYRIDINE DERIVATIVE;

ALLODYNIA; ANALGESIC ACTIVITY; ANIMAL EXPERIMENT; ANIMAL MODEL; AREA UNDER THE CURVE; ARTICLE; BINDING SITE; BIOLOGICAL ACTIVITY; BRAIN-TO-PLASMA RATIO; CALCIUM TRANSPORT; CONTROLLED STUDY; DRUG BIOAVAILABILITY; DRUG BLOOD LEVEL; DRUG BRAIN LEVEL; DRUG CLEARANCE; DRUG DESIGN; DRUG HALF LIFE; DRUG SYNTHESIS; EMBRYO; HUMAN; HUMAN CELL; HYDROGEN BOND; IC50; IN VITRO STUDY; MALE; MAXIMUM PLASMA CONCENTRATION; MEAN RESIDENCE TIME; METABOLIC STABILITY; NEUROPATHIC PAIN; NONHUMAN; RAT; STRUCTURE ACTIVITY RELATION; TIME TO MAXIMUM PLASMA CONCENTRATION; ANIMAL; ANTAGONISTS AND INHIBITORS; CELL CULTURE; CHEMISTRY; DISEASE MODEL; DRUG DEVELOPMENT; DRUG EFFECTS; EVALUATION STUDY; HEK293 CELL LINE; LIVER MICROSOME; METABOLISM; NEURALGIA; ORAL DRUG ADMINISTRATION; SPRAGUE DAWLEY RAT; TISSUE DISTRIBUTION;

ADMINISTRATION, ORAL; ANALGESICS; ANIMALS; CELLS, CULTURED; DISEASE MODELS, ANIMAL; DRUG DISCOVERY; HEK293 CELLS; HUMANS; MALE; MICROSOMES, LIVER; NEURALGIA; NITRILES; PYRIDINES; RATS; RATS, SPRAGUE-DAWLEY; RECEPTORS, METABOTROPIC GLUTAMATE; STRUCTURE-ACTIVITY RELATIONSHIP; TISSUE DISTRIBUTION;

EID: 84929311773     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2015.04.060     Document Type: Article

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