Synthesis and Antimicrobial Activity of 3-(1,3,4-Oxadiazol-2-yl)quinazolin-4(3H)-ones

Abstract

In attempt to find new pharmacologically active molecules, we report here the synthesis and in vitro antimicrobial activity of various 3-(1,3,4-oxadiazol-2-yl)-quinazolin-4(3H)-ones. The antimicrobial activity of title compounds were examined against two gram positive bacteria (S. aureus, S. pyogenes), two gram negative bacteria (E. coli, P. aeruginosa) and three fungi (C. albicans, A. niger, A. clavatus) using the broth microdilution method. Some derivatives bearing a bromo or iodo group exhibited very good antimicrobial activity.

Synthesis and Crystal Structure of 3-(4-Methoxyphenyl)-2-thioxo-2,3-dihydroquinazolin-4(1H)-one

“…4-Methoxyaniline in DMSO was treated with carbon disulfide and aqueous sodium hydroxide to afford sodium 4-methoxyphenylcarbamodithioate (1) followed by reaction with dimethyl sulfate to furnish the methyl 4-methoxyphenylcarbamodithioate (2). A solution of (2) in ethanol (20 mL) was treated with methyl anthranilate in presence of anhydrous potassium carbonate to provide the methyl 2-(3-(4-methoxyphenyl)thioureido)benzoate as intermediate (3), which on basic hydrolysis yielded the title compound (4) which was recrystallized from ethanol as colorless crystals.…”

“…It is a very important heterocycle exhibiting excellent pharmacological activities such as antimicrobial [2], antifungal [3], antitumor [4], anticancer [5], antiinflammatory [6], antidepressant [7], and anticonvulsant [8] activities. 3-Aryl-2-thioxo-2,3-dihydroquinazolin-4(1H)-one are derivatives of quinazolinones have a wide range of pharmacological and biological activities such as anticonvulsant and antitumor [9].…”

The synthesis and evaluation of anti-acetylcholinesterase activity of some 4(3H)-quinazolinone derivatives bearing substituted 1,3,4- thiadiazole

“…The asymmetric and symmetric strectching bands of c-h were observed at 2999-2849 cm -1 . ın addition, the absorption bands at 1682-1668 cm -1 (quinazoline ring c=o), 1444-1609 cm -1 (aromatic c=c strectching band and n-h bending band), 816-835 cm -1 (characterized phenyl ring substitution bands) and 698-683 cm -1 (thiadiazole ring c-S-c stretching bands) were detected (20)(21)(22). h-nMR spectra of these compounds, the signals representating the quinazoline ring methyl proton at second site appeared at 2.08-2.18 ppm as a singlet whereas methyl protons of 5c compound appeared at 2.13-2.17 ppm as a double singlet.…”

Synthesis and Crystal Structure of 1-(3-Fluorophenyl)-2-thioxo-2,3-dihydroquinazolin-4(1H)-one

“…It is a very important heterocycle exhibiting excellent pharmacological activities such as antimicrobial [2], antifungal [3], antitumor [4], anticancer [5], antiinflammatory [6], antidepressant [7] and anticonvulsant [8] activities. 3-Aryl-2-thioxo-2,3-dihydroquinazolin-4(1H)-one are a subclass quinazolinones having a wide range of applications including pharmacological and biological activities and important building blocks a variety of…”