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Molecules 2013, 18(3), 2683-2711; doi:10.3390/molecules18032683
Article

Synthesis, Antibacterial and Antifungal Activity of Some New Pyrazoline and Pyrazole Derivatives

Received: 31 October 2012; in revised form: 7 January 2013 / Accepted: 9 January 2013 / Published: 28 February 2013
(This article belongs to the Special Issue Heterocycles)
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Abstract: A series of 2-pyrazolines 59 have been synthesized from α,β-unsaturated ketones 24. New 2-pyrazoline derivatives 1315 bearing benzenesulfonamide moieties were then synthesized by condensing the appropriate chalcones 24 with 4-hydrazinyl benzenesulfonamide hydrochloride. Ethyl [1,2,4] triazolo[3,4-c][1,2,4]triazino[5,6-b]-5H-indole-5-ethanoate (26) and 1-(5H-[1,2,4]triazino[5,6-b] indol-3-yl)-3-methyl-1H-pyrazol-5(4H)-one (32) were synthesized from 3-hydrazinyl-5H-[1,2,4]triazino[5,6-b]indole (24). On the other hand ethyl[1,2,4]triazolo[3,4-c][1,2,4]triazino[5,6-b]-5,10-dihydroquinoxaline- 5-ethanoate (27) and 1-(5,10-dihydro-[1,2,4]triazino[5,6-b]quinoxalin-3-yl)-3-methyl-1H-pyrazol-5(4H)-one (33) were synthesized from 3-hydrazinyl-5,10-dihydro-[1,2,4]triazino[5,6-b]quinoxaline (25) by reaction with diethyl malonate or ethyl acetoacetate, respectively. Condensation of 6,6-dimethyl-4-oxo-4,5,6,7-tetrahydro-1H-indole-2-carbaldehyde (1') with compound 24 or 25 afforded the corresponding Schiff's bases 36 and 37, respectively. Reaction of the Schiff's base 37 with benzoyl hydrazine or acetic anhydride afforded benzohydrazide derivative 39 and the cyclized compound 40, respectively. Furthermore, the pyrazole derivatives 4244 were synthesized by cyclization of hydrazine derivative 25 with the prepared chalcones 24. All the newly synthesized compounds have been characterized on the basis of IR and 1H-NMR spectral data as well as physical data. Antimicrobial activity against the organisms E. coli ATCC8739 and P. aeruginosa ATCC 9027 as examples of Gram-negative bacteria, S. aureus ATCC 6583P as an example of Gram-positive bacteria and C. albicans ATCC 2091 as an example of a yeast-like fungus have been studied using the Nutrient Agar (NA) and Sabouraud Dextrose Agar (SDA) diffusion methods. The best performance was found for the compounds 16, 17, 19 and 20.
Keywords: chalcones; pyrazoline; pyrazole; carbothioamide; benzenesulfonamide; thiazolidine; indole; quinoxaline chalcones; pyrazoline; pyrazole; carbothioamide; benzenesulfonamide; thiazolidine; indole; quinoxaline
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MDPI and ACS Style

Hassan, S.Y. Synthesis, Antibacterial and Antifungal Activity of Some New Pyrazoline and Pyrazole Derivatives. Molecules 2013, 18, 2683-2711.

AMA Style

Hassan SY. Synthesis, Antibacterial and Antifungal Activity of Some New Pyrazoline and Pyrazole Derivatives. Molecules. 2013; 18(3):2683-2711.

Chicago/Turabian Style

Hassan, Seham Y. 2013. "Synthesis, Antibacterial and Antifungal Activity of Some New Pyrazoline and Pyrazole Derivatives." Molecules 18, no. 3: 2683-2711.



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