SYNTHESIS AND DIURETIC ACTIVITY OF 4,5-DIHYDRO-6H-IMIDAZO[4,5,1-IJ]QUINOLINE-6-ONE 6-OXIME-O-SULFONIC ACID-DERIVATIVES

Using our previously reported -2,3-dihydro-1-(2-methylbenzoyl)-4(1H)-q uinolinone 4-oxime-O-sulfonic acid potassium salt 1a (M17055) as a lea d, a series of tricyclic (2a-o, 3, 4, 5) and tetracyclic (6) quinolino ne oxime O-sulfonic acid derivatives were synthesized by ring annulati on of the 1-(2-methylbenzoyl) moiety to the quinolinone skeleton. They were compared with furosemide and compound la for diuretic activity i n dogs; some tricyclic 4,5-dihydro-6H-imidazo[4,5,1-ij]quinoline-6-one 6-oxime-O-sulfonic acid derivatives showed diuretic activity comparab le (2c,e) or superior (2m) to the lead compound la. These results are discussed on the basis of a comparison of the conformational and elect ronic characteristics of the relevant compounds with the aid of comput er graphics. (C) Elsevier, Paris.