title: Synthesis, spectral characterization, self-assembly and biological studies of N-acyl-2-pyrazolines bearing long alkoxy side chains.
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.
authors.affiliation: Department of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan. Electronic address: profazmi@hotmail.com.
authors.forename: Asghar
authors.initials: A
authors.lastname: Abbas
authors.affiliation: Department of Biochemistry, Pir Mehr Ali Shah Arid Agriculture University, Rawalpindi, Pakistan.
authors.forename: Habiba
authors.initials: H
authors.lastname: Nazir
authors.affiliation: Department of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan. Electronic address: moazzam@qau.edu.pk.
authors.forename: Muhammad Moazzam
authors.initials: MM
authors.lastname: Naseer
authors.affiliation: Institut fur Anorganische Chemie, J.W. Goethe-Universitat Frankfurt, Max-von-Laue-Str. 7, 60438 Frankfurt/Main, Germany.
authors.forename: Michael
authors.initials: M
authors.lastname: Bolte
authors.affiliation: Department of Forensic Medicine & Toxicology, National University of Science and Technology, Islamabad 44000, Pakistan.
authors.forename: Safdar
authors.initials: S
authors.lastname: Hussain
authors.affiliation: Department of Forensic Medicine & Toxicology, IIMC, Riphah International University Islamabad, Pakistan.
authors.forename: Noureen
authors.initials: N
authors.lastname: Hafeez
authors.affiliation: Department of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan; Department of Chemistry, Faculty of Science, University of Malaya, Kuala Lumpur 50603, Malaysia.
authors.forename: Aurangzeb
authors.initials: A
authors.lastname: Hasan
mesh_terms: D000438:Alcohols / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D000893:Anti-Inflammatory Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D000935:Antifungal Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D002478:Cells, Cultured; D018360:Crystallography, X-Ray; D003881:Dermatomycoses / Q000188:drug therapy; D006801:Humans; D008864:Microsporum / Q000187:drug effects; D008958:Models, Molecular; D009504:Neutrophils / Q000187:drug effects / Q000276:immunology; D011720:Pyrazoles / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*
chemical_list: D000438:Alcohols; D000893:Anti-Inflammatory Agents; D000935:Antifungal Agents; D011720:Pyrazoles; C059688:alkoxyl radical
keywords: Anti-inflammatory; Antifungal; Pyrazolines; Self assembly; Spectral characterization