Azza R. Maarouf, E. R. El-Bendary, F. Goda
Oct 1, 2004
Citations
0
Influential Citations
36
Citations
Journal
Archiv der Pharmazie
Abstract
A new series of quinazolin‐4(3H)‐one derivatives containing either a thiazole or a 1, 3, 4‐thiadiazole moiety were prepared in order to study the effect of such a heterocyclic combination on the expected diuretic activity. Synthesis of the target compounds (2, 4, and 6) has been achieved through an interaction of the starting 7‐chloro‐2‐methyl‐4H‐3, 1‐benzoxazin‐4‐one 1 with different heterocyclic amines. Alkylation of 3‐(2‐mercapto‐1, 3, 4‐thiadiazol‐5‐yl)quinazolin‐4(3H)‐one derivative 4 with different alkyl halides or chloroacetic acid afforded the corresponding thioethers 5 while interaction of 2‐methyl‐3‐(1, 3, 4‐thiadiazol‐5‐yl or thiazol‐5‐yl)quinazolin‐4(3H)‐ones (2 and 6) with various aromatic aldehydes resulted in the formation of the arylvinyl analogs 3 and 7, respectively. On the other hand, 2‐morpholinomethyl‐3‐(2‐sulfamoyl or mercapto‐1, 3, 4—thiadiazol‐5‐yl)quinazolin‐4(3H)‐one derivatives 10 have also been synthesized through an interaction of the sulfonamide or thiol analog 9 with the appropriate amine. Biological evaluation of some of the target compounds as diuretic agents was carried out. The results showed that 2‐[2‐(4‐chlorophenyl)vinyl]‐7‐chloro‐3‐(2‐sulfamoyl‐1, 3, 4‐thiadiazol‐5‐yl)quinazolin‐4(3H)‐one 7b exhibited significant diuretic activity. The detailed synthesis, spectroscopic and biological data are reported.