Synthesis and selective antitubercular and antimicrobial inhibitory activity of 1-acetyl-3,5-diphenyl-4,5-dihydro-(1h)-pyrazole derivatives

The new compounds 1-aryl-3-{1-phenyl-3-[p (methylthio)phenyl]pyrazol-4-yl}-2-propen-1-ones 2a?l were prepared by the condensation of 1-phenyl-3-[p (methylthio)phenyl]-4-formylpyrazole 1 with different aryl ketones. Compounds 2a?l in reaction with hydrazine hydrate yielded 3-aryl-5-{1-phenyl-3-[p-(methylthio)phenyl]pyrazol-4 yl}-4,5-dihydro-(1H)-pyrazoles 3a?l and in the presence of hydrazine hydrate in glacial acetic acid gave 1-acetyl-3-aryl 5-{1-phenyl-3-[p-(methylthio)phenyl]pyrazol-4-yl}-4,5 dihydro-(1H)-pyrazoles 4a?l. These compounds were tested in vitro for their antitubercular and antimicrobial activities. The in vitro antimycobacterial activity of the newly synthesized compounds was investigated against Mycobacterium tuberculosis H37RV (ATCC 27294) in BACTEC 12B medium using the ALAMAR radiometric system. The antimicrobial in vitro activity was tested against Bacillus coccous, Bacillus subtilis Escherichia coli, Proteus vulgaris and antifungal activity against Aspergillus niger. The structures of the synthesized compounds were assigned on the basis of elemental analysis IR, 1H NMR and mass spectral data. Nova jedinjenja 1-aril-3-{1-fenil-3-[p-(metiltio)fenil]-pirazol-4-il}-2-propen-1-oni 2a-l dobijena su kondenzacijom 1-fenil-3-[p-(metiltio)fenil]-4-formilpirazola 1 sa razlicitim arilketonima. Jedinjenja 2a-l u reakciji sa hidrazinhidratom dala su 3-aril 5-{1-fenil-3-[p-(metiltio)fenil]-pirazol-4-il}-4,5-dihidro-(1H)-pirazole 3a-l i u prisustvu hidrazinhidrata u glacijalnoj sircetnoj kiselini 1-acetil-3-aril-5-{1-fenil 3-[p-(metiltio)fenil]-pirazol-4-il}-4,5-dihidro-(1H)-pirazole 4a-l. Ova jedinjenja su testirana in vitro na antituberkulinsku i antibakterijsku aktivnost. In vitro antigljivic na i antibakterijska aktivnost sintetizovanih jedinjenja ispitivana je prema Mycobacterium tuberculosis H37RV (ATCC 27924) u BACTEC 12B sredini koriscenjem ALAMAR radiometrijskog sistema. Antimikrobna aktivnost in vitro testirana je prema Bacillus coccous, Bacillus subtilis Escherichia coli, Proteus vulgaris, kao i antigljivicna aktivnost prema Aspergillus niger. Struktura sintetizovanih jedinjenja definisana je na osnovu elementalne analize, IR, 1HNMR i masenospektrometrijskih podataka.