Abstract
Heterocyclic compounds are very widely distributed in nature and very abundant in plant andanimalproducts. They are included in many biochemical materials essential for life like nucleicacids(nucleotides), sugars and their derivatives, vitamin C and also, most members of vitaminBgroup(vitamin B6- pyridoxine). They are also found in application of diverse field such as agriculture,pharmaceutical and manufacturing industries. Researches have shown that heterocyclicnuclei givehigh chemotherapeutic values such as anti-malaria, anti-diabetics, anticancer and also act as aremedyfor the development of novel drugs. Imidazole containing moiety occupied a unique position in organic compounds. It is a five-memberednitrogenous heterocyclic moiety that has three carbons, two nitrogens, four hydrogen atoms, andtwodouble bonds having general molecular formula of C3H4N2. It is also known as 1,3-diazolebecauseof the nitrogen atoms present at the first and third positions (non–adjacent position) of thering, onenitrogen bear a hydrogen atom as the pyridine structure, and the other is called pyrrole typenitrogenand position four and five are equivalent. It formed the basis of many therapeutic natural productssuch as histamine, purine, histidine among others The research work focuses on the synthesis, characterization and antimicrobial activitiesofthederivatives of some new imidazole derivatives. Wallach synthesis was used to synthesize 1-methyl-5-chloro-imidazole which was nitrated to give 1-methyl-4-nitro-5-chloroimidazole. H2Sgas wasbubbleinto the solution 1-methyl-4-nitro-5-chloroimidazole in the presence of sodiumethoxide whichgave62% yield of 1-methyl-4-nitroimidazole-5-thiol (compound 4). Compound 4 was coupledwithbenzoylchloride and phenylethylbromide to produce compound 4B and 4A respectively. 1-methyl-4-nitroimidazole-5-thiol underwent oxidative chlorination to yield an unstable intermediateof1-methyl-4-nitroimidazole-5–sulfonyl chloride. All attempt to stabilized 1-methyl-4-nitroimidazole-5–sulfonyl chloride failed. With the sulfonyl chloride at position 5 on imidazole ring, it wasthencoupled with proline, proline methylester, biphenylhydroxide, 2-aminophenol and N- ethylanilinewhich yielded 1-methyl-4-nitroimidazole-5- lphonylproline,1-methyl-4-nitroimidazole-5-sulphonylprolinemethylester, 1-methyl-4-nitroimidazole-5-sulphonyl(2-hydroxylbiphenyl), 1-methyl-4-nitroimidazole-5-sulphonyl(2-aminophenol),1-methyl-4-nitroimidazole-5-sulphonyl(N- ethylaniline). The 4-nitro-2-methyl-1-H-ethanolyimidazole was chlorosulfonated with thionyl chloride, andthencoupled with aniline and 2,4 dichloroaniline to give 1-chloroethane-2-[thioacylaniline-4-nitroimidazole and 1-chloroethane-2-[thioacyl-(2,4-dichloroaniline)]-4-nitroimidazole respectively.The synthesized compounds were purified and confirmed using thin layer chromatography(TLC) and column chromatography, FT-IR, 1HNMR and 13CNMR spectral and were evaluatedforAnti-bacterial activity against Staphylococcus aureus, Pseudomonas aeruginosa, Escherichiacoli,Klebsiella pneumoniae and Bacillus subtilis and Anti-fungal activity against CandidaalbicansandAspergillus niger