Reduction of 3,5,7,7,10,12,14,14-octamethyl-1,4,8,11-tetraazacyclotetradeca-4,11-diene (Me8[14]diene) with sodium borohydride yields three diastereomeric Me8[14]anes. These diastereomers can be separated through fractional crystallization from xylene. The structure of these isomers has been established on the bseis of their NMR spectra. The structure of one isomer has been confirmed by X-ray crystallography.
4-Aminoantipyrine and 1,4-diaminobutane react with 4-isothiocyanato-4-methylpentan-2-one to give condensation products 1 and 2 respectively. Condensation of p-nitroaniline with 4-isothiocyanatobutan-2-one gave thiourea derivative 3 however coupling with 4-methyl-2-nitroaniline and 4-methoxy-2-nitroaniline gave cyclized products 5 and 6. 3,4-Diaminobenzophenone on condensation with 4-isothiocyanato-4-methylpentan-2-one in the presence of THF gave product 7 whereas the same reaction using methanol as solvent gave a mixture of hydroxy and methoxy compounds i.e. 8 which on treatment with acid under reflux temp. of MeOH gave pyrimidobenzimidazole derivative 9 in good yields. SMethyl pyrimidobenzimidazole derivative 10 was obtained by treating 9 with methanol under strongly acidic conditions. Pyrimidobenzimidazole 9 on reaction with methyl bromoacetate and ethyl bromoacetate gave compounds 11 and 12 respectively. Anti-inflammatory activity was carried out at 100 mg /kg p.o. of compounds 1-3 and 5-12. Compounds 5, 6, 8 and 10 showed 11,18,25 and 22% activity respectively whereas all other compounds were found to be inactive. Analgesic activity evaluation of 1, 2, 7-9 and 12 showed that compounds 2, 7 and 12 exhibited 50, 25 and 60% at 100 mg/kg p.o. and 50, 25 and 40% activity at 50 mg/kg p.o. respectively where as compounds 1, 8 and 9 were found to be inactive.
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.