Investigations on the 4-quinolone-3-carboxylic acid motif. 6. Synthesis and pharmacological evaluation of 7-substituted quinolone-3-carboxamide derivatives as high affinity ligands for cannabinoid receptors

European Journal of Medicinal Chemistry

Volumn 58, Issue , 2012, Pages 30-43

  Pasquini, Serena ^a   De Rosa, Maria ^a   Ligresti, Alessia ^b   Mugnaini, Claudia ^a   Brizzi, Antonella ^a   Caradonna, Nicola P ^c   Cascio, Maria Grazia ^d   Bolognini, Daniele ^d   Pertwee, Roger G ^d   Di Marzo, Vincenzo ^b   Corelli, Federico ^a  

^a UNIVERSITY OF SIENA   (Italy)

^b CNR   (Italy)

^c Siena Biotech SpA   (Italy)

^d UNIVERSITY OF ABERDEEN   (United Kingdom)

Author keywords

Cannabinoid ligands; Partial agonists; Peripheral ligands; Quinolones; Synthesis

Indexed keywords

4 [3 (1,3,3 TRIMETHYLBICYCLO[2.2.1]HEPTAN 2 YL)CARBAMOYL] 4 OXO 7 (PHENYLTHIO) 1,4 DIHYDROQUINOLIN 1 YL]BUTYL ACETATE; 4 [3 (1,3,3 TRIMETHYLBICYCLO[2.2.1]HEPTAN) 2 YLCARBAMOYL] 7 FLUORO 4 OXO 1,4 DIHYDROQUINOLIN 1 YL]BUTYL ACETATE; AMIDE; CANNABINOID RECEPTOR; CARBOXYLIC ACID; N (1,3,3 TRIMETHYLBICICLO[2.2.1]HEPTAN 2 YL) 1 BUTYL 7 FLUORO 4 OXO 1,4 DIHYDROQUINOLINE 3 CARBOXAMIDE; N (1,3,3 TRIMETHYLBICICLO[2.2.1]HEPTAN 2 YL) 1 ETHYL 7 FLUORO 4 OXO 1,4 DIHYDROQUINOLINE 3 CARBOXAMIDE; N (1,3,3 TRIMETHYLBICYCLO[2.2.1]HEPTAN 2 YL) 1 (2 METHOXYETHYL) 4 OXO 7 (PHENYLTHIO) 1,4 DIHYDROQUINOLINE 3 CARBOXAMIDE; N (1,3,3 TRIMETHYLBICYCLO[2.2.1]HEPTAN 2 YL) 1 (3 METHYL) BENZYL 7 FLUORO 4 OXO 1,4 DIHYDROQUINOLINE 3 CARBOXAMIDE; N (1,3,3 TRIMETHYLBICYCLO[2.2.1]HEPTAN 2 YL) 1 (3 METHYL)BENZYL 4 OXO 7 (PHENYLTHIO) 1,4 DIHYDROQUINOLINE 3 CARBOXAMIDE; N (1,3,3 TRIMETHYLBICYCLO[2.2.1]HEPTAN 2 YL) 1 (4 HYDROXYBUTYL) 4 OXO 7 (PHENYLTHIO) 1,4 DIHYDROQUINOLINE 3 CARBOXAMIDE; N (1,3,3 TRIMETHYLBICYCLO[2.2.1]HEPTAN 2 YL) 1 [2 (DIMETHYLAMINO)ETHYL] 4 OXO 7 (PHENYLTHIO) 1,4 DIHYDROQUINOLINE 3 CARBOXAMIDE; N (1,3,3 TRIMETHYLBICYCLO[2.2.1]HEPTAN 2 YL) 1 [2 (DIMETHYLAMINO)ETHYL] 7 FLUORO 4 OXO 1,4 DIHYDROQUINOLINE 3 CARBOXAMIDE; N (1,3,3 TRIMETHYLBICYCLO[2.2.1]HEPTAN 2 YL) 1 BUTYL 4 OXO 7 (PHENYLTHIO) 1,4 DIHYDROQUINOLINE 3 CARBOXAMIDE; N (1,3,3 TRIMETHYLBICYCLO[2.2.1]HEPTAN 2 YL) 1 ETHYL 4 OXO 7 (PHENYLTHIO) 1,4 DIHYDROQUINOLINE 3 CARBOXAMIDE; N (1,3,3 TRIMETHYLBICYCLO[2.2.1]HEPTAN 2 YL) 1 METHYL 4 OXO 7 (PHENYLTHIO) 1,4 DIHYDROQUINOLINE 3 CARBOXAMIDE; N (1,3,3 TRIMETHYLBICYCLO[2.2.1]HEPTAN 2 YL) 4 OXO 1 PENTYL 7 (PHENYLTHIO) 1,4 DIHYDROQUINOLINE 3 CARBOXAMIDE; N (1,3,3 TRIMETHYLBICYCLO[2.2.1]HEPTAN 2 YL) 4 OXO 7 (PHENYLTHIO) 1 [4 (PHENYLTHIO)BUTYL] 1,4 DIHYDROQUINOLINE 3 CARBOXAMIDE; N (1,3,3 TRIMETHYLBICYCLO[2.2.1]HEPTAN 2 YL) 4 OXO 7 (PHENYLTHIO) 1 PROPYL 1,4 DIHYDROQUINOLINE 3 CARBOXAMIDE; N (1,3,3 TRIMETHYLBICYCLO[2.2.1]HEPTAN 2 YL) 7 FLUORO 1 (2 METHOXYETHYL) 4 OXO 1,4 DIHYDROQUINOLINE 3 CARBOXAMIDE; N (1,3,3 TRIMETHYLBICYCLO[2.2.1]HEPTAN 2 YL) 7 FLUORO 1 (4 HYDROXYBUTYL) 4 OXO 1,4 DIHYDROQUINOLINE 3 CARBOXAMIDE; N (1,3,3 TRIMETHYLBICYCLO[2.2.1]HEPTAN 2 YL) 7 FLUORO 1 METHYL 4 OXO 1,4 DIHYDROQUINOLINE 3 CARBOXAMIDE; N (1,3,3 TRIMETHYLBICYCLO[2.2.1]HEPTAN 2 YL) 7 FLUORO 4 OXO 1 PENTYL 1,4 DIHYDROQUINOLINE 3 CARBOXAMIDE; N (1,3,3 TRIMETHYLBICYCLO[2.2.1]HEPTAN 2 YL) 7 FLUORO 4 OXO 1 PROPYL 1,4 DIHYDROQUINOLINE 3 CARBOXAMIDE; N (1,3,3 TRIMETHYLBICYCLO[2.2.1]HEPTAN 2 YL) 7 FLUORO 4 OXO 1 VINYL 1,4 DIHYDROQUINOLINE 3 CARBOXAMIDE; N (3,4 DICHLOROBENZYL) 4 OXO 1 PENTYL 7 PHENYL 1,4 DIHYDROQUINOLINE 3 CARBOXAMIDE; N (3,4 DICHLOROBENZYL) 7 BROMO 4 OXO 1 PENTYL 1,4 DIHYDROQUINOLINE 3 CARBOXAMIDE; N ISOPROPYL 4 OXO 1 PENTYL 7 (PHENYLTHIO) 1,4 DIHYDROQUINOLINE 3 CARBOXAMIDE; N',N' DIMETHYL 4 OXO 1 PENTYL 7 (PHENYLTHIO) 1,4 DIHYDROQUINOLINE 3 CARBOHYDRAZIDE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANIMAL CELL; ARTICLE; BINDING AFFINITY; BLOOD BRAIN BARRIER; CELL MEMBRANE PERMEABILITY; CONTROLLED STUDY; DRUG SYNTHESIS; FEMALE; NONHUMAN; STRUCTURE ACTIVITY RELATION;

ANIMALS; CELL LINE; CHO CELLS; CRICETINAE; DOGS; DOSE-RESPONSE RELATIONSHIP, DRUG; HUMANS; LIGANDS; MOLECULAR STRUCTURE; QUINOLONES; RECEPTOR, CANNABINOID, CB1; RECEPTOR, CANNABINOID, CB2; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84867589575     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2012.09.035     Document Type: Article

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