Synthesis, biological evaluation, and docking studies of 3-(substituted)-aryl-5-(9-methyl-3-carbazole)-1H-2-pyrazolines as potent anti-inflammatory and antioxidant agents

Babasaheb P Bandgar; Laxman K Adsul; Hemant V Chavan; Shivkumar S Jalde; Sadanand N Shringare; Rafique Shaikh; Rohan J Meshram; Rajesh N Gacche; Vijay Masand

doi:10.1016/j.bmcl.2012.07.080

Synthesis, biological evaluation, and docking studies of 3-(substituted)-aryl-5-(9-methyl-3-carbazole)-1H-2-pyrazolines as potent anti-inflammatory and antioxidant agents

Bioorg Med Chem Lett. 2012 Sep 15;22(18):5839-44. doi: 10.1016/j.bmcl.2012.07.080. Epub 2012 Jul 31.

Authors

Babasaheb P Bandgar¹, Laxman K Adsul, Hemant V Chavan, Shivkumar S Jalde, Sadanand N Shringare, Rafique Shaikh, Rohan J Meshram, Rajesh N Gacche, Vijay Masand

Affiliation

¹ Medicinal Chemistry Research Laboratory, School of Chemical Sciences, Solapur University, Solapur 413 255, Maharashtra, India. [email protected]

PMID: 22901385
DOI: 10.1016/j.bmcl.2012.07.080

Abstract

A novel series of 3-(substituted)-aryl-5-(9-methyl-3-carbazole)-1H-2-pyrazolines (5a-o) has been synthesized and the structures of newly synthesized compounds were characterized by IR, (1)H NMR and mass spectral analysis. All the synthesized compounds were evaluated for their in vitro and in vivo anti-inflammatory activity, and also for their antioxidant activity. Compounds 5b, 5c, 5d and 5n were found to be selective COX-2 inhibitors. Compound 5c was found to potent inhibitor of the carrageenin induced paw edema in rats. Most of the compounds exhibited good DPPH and superoxide radical scavenging activity, while compounds 5c, 5d, 5i and 5k exhibited good hydroxyl radical scavenging activity. Molecular docking result, along with the biological assay data, suggested that compound 5c was a potential anti-inflammatory agent.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Animals
Anti-Inflammatory Agents, Non-Steroidal / chemical synthesis*
Anti-Inflammatory Agents, Non-Steroidal / chemistry
Anti-Inflammatory Agents, Non-Steroidal / pharmacology*
Antioxidants / chemical synthesis*
Antioxidants / chemistry
Antioxidants / pharmacology*
Biphenyl Compounds / chemistry
Cyclooxygenase 1 / metabolism
Cyclooxygenase 2 / metabolism
Cyclooxygenase 2 Inhibitors / chemical synthesis
Cyclooxygenase 2 Inhibitors / chemistry
Cyclooxygenase 2 Inhibitors / pharmacology
Dose-Response Relationship, Drug
Edema / chemically induced
Edema / drug therapy*
Free Radical Scavengers / chemistry
Models, Molecular
Molecular Structure
Picrates / chemistry
Pyrazoles / chemical synthesis
Pyrazoles / chemistry
Pyrazoles / pharmacology*
Rats
Stereoisomerism
Structure-Activity Relationship
Superoxides / chemistry

Substances

Anti-Inflammatory Agents, Non-Steroidal
Antioxidants
Biphenyl Compounds
Cyclooxygenase 2 Inhibitors
Free Radical Scavengers
Picrates
Pyrazoles
Superoxides
1,1-diphenyl-2-picrylhydrazyl
Cyclooxygenase 1
Cyclooxygenase 2