Table of Contents
Advances in Chemistry
Volume 2014, Article ID 329681, 12 pages
http://dx.doi.org/10.1155/2014/329681
Research Article

Synthesis and Antimicrobial Studies of Pyrimidine Pyrazole Heterocycles

1Department of Chemistry, Bio-organic Laboratory, Kirori Mal College, University of Delhi, Delhi 110 007, India
2Department of Chemistry, Bio-organic Laboratory, University of Delhi, Delhi 110 007, India
3Centre for Biotechnology, Maharshi Dayanand University, Rohtak 124 001, India

Received 30 April 2014; Revised 19 July 2014; Accepted 29 July 2014; Published 25 August 2014

Academic Editor: Adriana I. Segall

Copyright © 2014 Rakesh Kumar et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Abstract

Prompted from the diversity of the wider use and being an integral part of genetic material, an effort was made to synthesize pyrimidine pyrazole derivatives of pharmaceutical interest by oxidative cyclization of chalcones with satisfactory yield and purity. A novel series of 1,3-dimethyl-6-hydroxy-2,4-dioxo-5-(1′-phenyl-3′-aryl-1H-pyrazol-5′-yl)-1,2,3,4-tetrahydropyrimidines (5a–d) and 1,3-diaryl-6-hydroxy-4-oxo-2-thioxo-5-(1′-phenyl-3′-aryl-1H-pyrazol-5′-yl)-1,2,3,4-tetrahydropyrimidines (5e–l) has been synthesized. The structures of these compounds were established on the basis of FT-IR, 1H NMR, 13C NMR, and mass spectral analysis. All the synthesized compounds were screened for their antimicrobial activity against bacteria and fungi. Among all the compounds, 5g was found to be the most active as its MIC was 31.25 µg/mL against S. aureus and B. cereus. The compounds 5h, 5c, and 5e also possess antibacterial activity with MIC values as 62.50, 125.00, and 500.00 µg/mL, respectively. The compounds 5c and 5j were found to have antifungal activity against Aspergillus spp. As antifungal drugs lag behind the antibacterial drugs, therefore we tried in vitro combination of these two compounds with standard antifungal drugs (polyene and azole) against Aspergillus spp. The combination of ketoconazole with 5c and 5j showed synergy at 1 : 8 (6.25 : 50.00 µg/mL) and 1 : 4 (25 : 100 µg/mL) against A. fumigatus (ITCC 4517) and A. fumigatus (VPCI 190/96), respectively.