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

Abstract

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.

Crystal structure of [3,5-dimethyl-4-(prop-2-ynyl)-1Hpyrazol- 1-yl](2-furyl)methanone, C13H12N2O2

“…Derivatives of pyrazoles represent one of the most active classes of compounds possessing aw ide spectrum of biological activities, such as antibacterial [1,2], antimicrobial [3][4][5][6], antiviral [7], antioxidant [8],a nti-inflammatory [9,10], anticonvulsant [11,12], anticancer [13], anesthetic and anti-arrhythmic activities [14].T he formation of the title compound is the result of intramolecular ring closure of intermediate N'-(3-acetylhex-5-yn-2-ylidene)furan-2-carbohydrazide obtained as the main product in the absence of PTSA. But the N'-(3-acetylhex-5-yn-2-ylidene)furan-2-carbohydrazide maybealso isomerized to N'-(3-acetylhex-2-en-5-yn-2-yl)furan-2-carbohydrazide.…”

The One-Step Synthesis of 3,4-Dihydropyrano[F]Chromene Derivatives in Under Grinding as an Environmentally Friendly Alternative

“…Compounds with an uracil moiety antitumor, antibacterial, antihypertensive, vasodilator, bronchiodilator, hepatoprotective, cardiotonic, and antiallergic activities. Some of them exhibit antimalarial, antifungal analgesics, and herbicidal properties [5][6][7][8][9] .…”

Synthesis and Antimicrobial Activity of Novel Series of Diversely Substituted Acetyl Pyrazoline Bearing Biphenyl Carbonitrile Motif

“…Pyrazoline compounds are acquiring more importance because of their immense biological and pharmacological potential. This class of compound possesses wide spectrum of biological activities such as antimicrobial [1,2,3], anti-inflammatory and analgesic [4,5], anticancer [6,7], antidepressant [8], anti-tuberculosis [9,10], antiamoebic [11] antioxidant [12,13], antihyperglycemic [14], anti-epileptic [15,16], anti-parkinson and anti-alzheimer [17].…”