Synthesis of new 3-aryl-4-(3-aryl-4,5-dihydro-1 H -pyrazol-5-yl)-1-phenyl-1 H -pyrazole derivatives as potential antimic
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Med Chem Res (2013) 22:2654–2664 DOI 10.1007/s00044-012-0267-8
ORIGINAL RESEARCH
Synthesis of new 3-aryl-4-(3-aryl-4,5-dihydro-1H-pyrazol-5-yl)-1phenyl-1H-pyrazole derivatives as potential antimicrobial agents Shridhar Malladi • Arun M. Isloor • S. K. Peethambar • Hoong Kun Fun
Received: 16 April 2012 / Accepted: 28 September 2012 / Published online: 9 October 2012 Ó Springer Science+Business Media New York 2012
Abstract New (E)-1-aryl-3-(3-aryl-1-phenyl-1H-pyrazol-4yl)prop-2-en-1-ones 6 (pyrazolic chalcones) were synthesized from Claisen–Schmidt reaction of 3-aryl-1-phenylpyrazol-4carboxaldehydes 4 with several acetophenone derivatives 5. Subsequently, the cyclocondensation reaction of chalcones 6 with phenylhydrazine in acetic acid medium afforded the new 3-aryl-4-(3-aryl-4,5-dihydro-1H-pyrazol-5-yl)-1-phenyl-1Hpyrazoles 7. The synthesized compounds were characterized by spectral studies and evaluated for their in vitro antibacterial activity against three pathogenic bacterial strains, Staphylococcus aureus, Escherichia coli, and Pseudomonas aeruginosa, and in vitro antifungal activity against three pathogenic fungal strains Aspergillus flavus, Chrysosporium keratinophilum, and Candida albicans. Keywords Claisen–Schmidt reaction Pyrazolic chalcones Pyrazolines Antimicrobial
S. Malladi A. M. Isloor (&) Medicinal Chemistry Laboratory, Department of Chemistry, National Institute of Technology Karnataka, Surathkal, Mangalore 575025, India e-mail: [email protected] S. K. Peethambar Department of Bio-Chemistry, Kuvempu University, Jnanasahyadri, Shankaraghatta 577451, Karnataka, India H. K. Fun X-Ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 Georgetown, Penang, Malaysia H. K. Fun Deparment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia
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Introduction Antimicrobial resistance is a global public health concern that is impacted by both human and non-human antimicrobial use. The consequences of antimicrobial resistance are particularly important when pathogens are resistant to antimicrobials that are critically important in the treatment of human disease. The treatment of microbial infections still remains an important and challenging therapeutic problem because of factors that include emerging infectious diseases and the increasing number of multidrugresistant microbial pathogens. In spite of the large number of antibiotics and chemotherapeutics available for medical use, the emergence of old and new antibiotic resistant bacterial strains in the last decades constitutes a substantial need for new classes of antibacterial agents (Chopra et al., 2008). It has been postulated that the development of resistance to known antibiotics could be overcome by identifying new drug targets via genomics, improving the existing nature of antibiotics, and identifying new antibacterial agents with novel mode of action and structure (Walsh, 2000; Ritter and Wong, 2001; Wijkmans and Beckett, 2002). 1,2-Diaryl substituted hetero
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