Affiliations 

  • 1 Department of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan. Electronic address: profazmi@hotmail.com
  • 2 Department of Biochemistry, Pir Mehr Ali Shah Arid Agriculture University, Rawalpindi, Pakistan
  • 3 Department of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan. Electronic address: moazzam@qau.edu.pk
  • 4 Institut fur Anorganische Chemie, J.W. Goethe-Universitat Frankfurt, Max-von-Laue-Str. 7, 60438 Frankfurt/Main, Germany
  • 5 Department of Forensic Medicine & Toxicology, National University of Science and Technology, Islamabad 44000, Pakistan
  • 6 Department of Forensic Medicine & Toxicology, IIMC, Riphah International University Islamabad, Pakistan
  • 7 Department of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan; Department of Chemistry, Faculty of Science, University of Malaya, Kuala Lumpur 50603, Malaysia
PMID: 24177882 DOI: 10.1016/j.saa.2013.10.023

Abstract

A series of new pyrazoline derivatives (1b-4c) bearing N-acyl arms and nine to twelve carbon long alkoxy side chains was synthesized and characterized on the basis of spectroscopic data and microanalysis. The nature of self-assembly to understand the interplay of alkoxy chain crystallization and various supramolecular interactions was investigated using single crystal X-ray diffraction studies. Interesting self-assembled supramolecular structures of 1b and 4c were observed in the crystal lattice owing to various CH⋯O, H⋯H, CH⋯π, lonepair⋯π and π⋯π interactions. Further, all the synthesized compounds (1b-4c) were screened for their in vitro antifungal and anti-inflammatory activities. Compounds 2b, 3b, 2c and 3c showed significant to moderate antifungal activity against Microsporum canis whereas most of the other compounds were found inactive against all the five tested fungal strains. Good anti-inflammatory activity was observed for compounds 1b with IC50 value 331 μM compared to 273 μM for Indomethacine, a standard reference drug. The bio-activity data demonstrates the relationship between lipophilicity, solubility and bioavailability.

* Title and MeSH Headings from MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine.