A simple method for the synthesis of title compounds is reported, which were isolated from a series of reactions. After a nucleophilic reaction of 2-phenyl-3,1-benzoxazin-4(3H)-one (1) with thiosemicarbazide to furnish quinazolinylthiourea (2), followed by cyclisation with chloroacetic acid, 3-[(4-oxo-1,3-thiazolidin-2-yliden)amino]-2-phenylquinazolin-4(3H)-one (3) was yielded, which was converted to corresponding arylidene derivatives (5a-f) by treatment with various aldehydes (4a-f). Subsequent condensation of (5a-f) with phthalimidoxyethylbromide gave title compounds (7a-f). The structure of isolated compounds has been determined by means of IR, 1 H NMR and mass spectroscopy.
Mebendazole is a well known anti-helimintic and belongs to the benzimidazole group of medicines. In order to achieve better medicinal results, i.e. enhanced activity and low toxicity, structural modifications are made in the existing drugs. Some 5-benzoyl-N-[1-(alkoxyphthalimido) benzimidazol-2-yl] carbamic acid methyl ester(3a-c)and 5-benzoyl-N-[1-(2,3-bis oxyphthalimido∕oxysuccinimido propyl benzimidazol-2-yl) carbamic acid methyl ester(7a-b)have been synthesized from two different routes. Structures of the compounds have been established on the basis of elemental analysis and spectral studies. All the synthesized compounds(3a-c)and(7a-b)were assayedin vitrofor antimicrobial activity against mebendazole (itself) and standard [ciprofloxacin (antibacterial) and fluconazole (antifungal)].
A number of 3-N-ethoxyphthalimido-5-amino-2-oxo-7-(4-substituted phenyl/2furyl/3,4-disubstituted phenyl) -1,3-thiazolo[4,5d]pyrimidines [5a-f] and 6-Nethoxyphthalimido-5-oxo 3-(4-substituted phenyl/2-furyl/3,4-disubstituted phenyl)-3,3adihydro[1,3] thiazole [4,5-c]isoxazoles [7a-f] derivatives have been proposed to synthesize from the condensation of phthalimidoxyethyl bromide with [4a-f] and [6a-f], respectively. The compounds [4a-f] and [6a-f] in turn have been prepared by the reaction of 5-(4-substituted phenyl/2-furyl/3,4-disubstituted phenyl)-1,3 thiazolidine -2,4-dione [3a-f] with guanidine nitrate and hydroxylamine hydrochloride, respectively. All the synthesized compounds were characterized by carbon and nitrogen elemental analysis and IR, 1H, NMR and mass spectral studies. All the final derivatives of titled compounds have been tested for their antifungal activities against Candida albicans and Aspergillus fumigatus and antibacterial activities against Bacillus subtilis, Klebsiella pneumoniae, Escherichia coli and Proteus mirabilis comparing with standard drugs.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.