Synthesis and Evaluation of some Novel Quinazolinone Derivatives as Diuretic Agents

Abstract

A new series of quinazolin-4(3H)-one derivatives containing either a thiazole or College of Pharmacy, a 1,3,4-thiadiazole moiety were prepared in order to study the effect of such a Mansoura University, heterocyclic combination on the expected diuretic activity. Synthesis of the target Mansoura 35516, Egypt compounds (2, 4, and 6) has been achieved through an interaction of the b Pharmaceutical Organic starting 7-chloro-2-methyl-4H-3,1-benzoxazin-4-one 1 with different heterocyclic Chemistry Departments, amines. Alkylation of 3-(2-mercapto-1,3,4-thiadiazol-5-yl)quinazolin-4(3H)-one College of Pharmacy, derivative 4 with different alkyl halides or chloroacetic acid afforded the correMansoura University, sponding thioethers 5 while interaction of 2-methyl-3-(1,3,4-thiadiazol-5-yl or thiMansoura 35516, Egypt azol-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-1,3,4Ϫthiadiazol-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.

An environmentally friendly approach for the synthesis of quinazolinone sulfonamide

“…Quinazolinone sulfonamides are considered as hybrid molecules which have been identified as biological active compounds and they showed extended biological activities, such as cancer chemotherapeutic agents [42][43][44], antimicrobial [45], and diuretic [46] activities ( Fig. 1).…”

Synthesis and antifungal activity of novel 5‐substituted 4‐(1,3,4‐thiadiazol‐2‐yl)benzene‐1,3‐diols

“…A large number of reports on their synthesis and biological activities have appeared during the past years [1][2][3][4][5][6][7][8]. Among them, 1,3,4-thiadiazoles with antifungal activity against phytopathogenic fungi are an interesting group of compounds [9][10][11][12].…”

Synthesis and antimicrobial activity of novel 1,3,4‐oxadiazolyl‐quinazolin‐4(3H)ones

“…1,3,4‐Oxadiazoles are five member nitrogen atom contained heterocycles, represent broad spectrum of biological activity in both agrochemicals and pharmaceuticals such as insecticidal [1], herbicidal [2], antibacterial [3], antifungal [4], analgesic [5], anti‐inflammatory [6], antimalarial [7], antiviral [8], anti‐HBV [9], antianexiety [10], anticancer [11], anti‐HIV [12], antitubercular [13], and anticonvulsant [14]. Quinazolin‐4(3 H )one derivatives are six member fused heterocycles, possess potent pharmacological activities like antibacterial [15], antifungal [16], analgesic [17], anti‐inflammatory [18], anthelminthic [19], antitumor [20], anticonvulsant [21], antihistaminic [22], anti HIV [23], antiproliferative [24], antitubercular [25], antiviral [26], CNS depressant [27], cytotoxicity [28], diuretic [29], and hypolipidemic [30].…”