European Journal of Medicinal Chemistry p. 267 - 277 (1998)
Update date:2022-08-05
Topics:
Nishijima, Kazumi
Shinkawa, Tomoaki
Yamashita, Yoshiaki
Sato, Naofumi
Nishida, Hidemitsu
Kato, Kazuo
Onuki, Yoshiaki
Mizota, Masahiro
Ohtomo, Kikuo
Miyano, Soutarou
The diuretic activity of 6-chloro-2,3-dihydro-1-propionyl-4(1H)-quinolinone 4-oxime 1 (M12285) was previously shown to derive from a 6-chloro-2,3-dihydro-1-propionyl-4(1H)-quinolinone 4-oxime-O-sulfonic acid salt as a rat metabolite. Thus, in the present study, the potassium salt 2 (M17000) was synthesized to unambiguously establish the structure as well as the stereochemistry of the oxime. The structural features of compounds 1 and 2 were compared with those of conventional diuretics by electrostatic potential maps. Using compound 2 as a lead compound, various quinolinone oxime sulfonic acid derivatives were synthesized and the diuretic activity for elucidation of the structure-activity relationships examined. Among the compounds synthesized, 7-chloro-2,3-dihydro-1-(2-methylbenzoyl)-4(1H)-quinolinone 4-oxime-O-sulfonic acid potassium salt 3 (M17055) showed a particularly high activity. Elsevier, Paris.
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Doi:10.1246/bcsj.71.1683
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