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Matsuoka, M., Segawa, J., Makita, Y., Ohmachi, S., Kashima, T., Nakamura, K.-I., Hattori, M., Kitano, M. and Kise, M. (1997) Studies on pyridonecarboxylic acids. V. A practical synthesis of ethyl 6,7-difluoro-1-methyl-4-oxo-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylate, a key intermediate for the new tricyclic quinolone, prulifloxacin (NM441) and versatile new syntheses of the 2-thioquinoline skeleton. Journal of Heterocyclic Chemistry, 34, 1773-1779.
doi:10.1002/jhet.5570340622
has been cited by the following article:
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TITLE:
3-Arylisothiazoloquinols As Potent Ligands for the Benzodiazepine Site of GABAA Receptors
AUTHORS:
Jakob Nilsson, Elsebet Østergaard Nielsen, Tommy Liljefors, Mogens Nielsen, Olov Sterner
KEYWORDS:
Isothiazolo[5, 4-b]quinolin-4(9H)-ones; Isoxazolo[5, 4-b]quinolin-4(9H)-ones; Benzodiazepine binding site; GABAA Receptors; GABAA Receptor Subtypes; Pharmacophore Model
JOURNAL NAME:
Journal of Biomedical Science and Engineering,
Vol.5 No.1,
January
12,
2012
ABSTRACT: 3-Arylisothiazolo[5,4-b]quinolin-4(9H)-ones and 3-arylisoxazolo[5,4-b]quinolin-4(9H)-ones were synthesized and assayed for affinity for the benzodiazepine binding site of the GABAA receptors. While the 3-arylisothiazoloquinolin-4-ones were found to be potent ligands, with affinities (expressed as the affinity Ki value) down to 1 nM, the 3-arylisoxazoloquinolin-4-ones are less potent. This is suggested to depend on sterical repulsive interaction of the 3-arylisoxazoloquinolin-4-ones with the receptor essential volume of the binding site, and a higher electron density at the nitrogen in the azole ring (N-2) as well as the carbonyl oxygen in the isothiazoloquinolin-4-ones enabling them to interact stronger with hydrogen bond donor sites at the binding site.