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ABSTRACT:
A series of N-(3,5-diphenyl-4,5-dihydro-1,2-oxazol-4-yl)methyl aniline)-n-(4-sulfamoylphenyl)benzamide and N-(3,5-diphenyl-4,5-dihydro-1,2-oxazol-4-yl)methyl aniline)benzene sulfonamide have been synthesized. Various aromatic ketone reacts with aromatic aldehyde using NaOH as a catalyst gives 1,3-diphenylprop-2-en-1-one, which on further refluxed with hydroxylamine hydrochloride using potassium hydroxide as a catalyst afforded isoxazoline. Thus obtained isoxazoline on further condensed with formaldehyde and benzocaine to give N-(3,5-diphenyl-4,5-dihydro-1,2-oxazol-4-yl)methyl aniline)-4-ethyl benzoate, which on further condensed with sulphanilamide to give N-(3,5-diphenyl-4,5-dihydro-1,2-oxazol-4-yl)methyl aniline)-n-(4-sulfamoylphenyl)benzamide (A1-5) .Isoxazoline also condensed with formaldehyde and sulphanilamide to give N-(3,5-diphenyl-4,5-dihydro-1,2-oxazol-4-yl)methyl aniline)benzene sulfonamide (A6-10). The structure of the synthesized compounds were evaluated by IR, 1H NMR and elemental analysis. All the compounds screened for antitubercular activity. Anti-tubercular activity was carried out by using middle brook 7H9 broth base ( M198 ) medium against Mycobacterium tuberculosis of H37Rv strain. Streptomycin was used as standard drug for comparison.
KEYWORDS: Mycobacterium tuberculosis, anti tubercular activity, aromatic ketone, aromatic aldehyde
INTRODUCTION:
Tuberculosis (TB) is an infectious disease that is caused by a bacterium called Mycobacterium tuberculosis. According to WHO, currently one third of world's populationi is infected with latent tuberculosis[1]. TB is responsible for deaths of over 2 million people annually worldwide. Moreover enhanced susceptibility to TB in HIV infected population is another serious health problem throughout the world. The increasing problem of Multi-Drug Resistant-tuberculosis has focused on developing new drugs that are active against drug resistant tuberculosis. Isoxazoline derivatives reported wide varieties of activities, antiulcerogenic[2], anti-inflammatory[3], antidepressant[4], antiplatelet[5], antiviral[6], fungicides[7], bactericidal[8], anti - TB activity[9]. The structures of all new compounds were confirmed by their IR, 1H-NMR, Mass spectra and by elemental analysis. This prompted us to undertake an exhaustive investigation of synthesis and evaluation of anti -TB activity of various isoxazoline derivatives.
MATERIALS AND METHODS:
Melting point were taken in open capillary tubes and are uncorrected. The purity of the compounds was confirmed by thin layer chromatography using silica gel -G coated plates and spots were located by iodine. Analytical data of C, H and N were within ±0.4% of the theoretical values and their structure were elucidated by IR in KBr on Thermo Nicolet IR-200 spectrometer,1H-NMR specrtra were recorded in DMSO...