Anti-Inflammatory & Anti-Allergy Agents in Medicinal Chemistry Sujeet Kumar Gupta 1* and Ashutosh Mishra 2 1 Department of Pharmaceutical Chemistry, Hygia Institute of Pharmaceutical Education and Re- search, Lucknow-206020, India; 2 Department of Pharmaceutical Chemistry, Acharya Narendra Deo College of Pharmacy, Babhnan, Gonda-271313, India A R T I C L E H I S T O R Y Received: December 14, 2015 Revised: February 09, 2016 Accepted: February 10, 2016 DOI: 10.2174/187152301566616021012 4545 Abstract: Background: Non-steroidal anti-inflammatory drugs (NSAIDS) are clinically used as anti-inflammatory, analgesic and antipyretic agents but they have the drawbacks such as gastric irritation and gastric ulceration. Recently, quinoline derivatives have shown signifi- cant anti-inflammatory and less ulcerogenic activity. The present study deals with the synthe- sis and pharmacological assessment of a series of novel quinoline derivatives bearing azetidi- nones scaffolds as anti-inflammatory and analgesic agents. Methods: A series of newer 3-chloro-1-(substituted)-4-(tetrazolo [1,5-a]quinolin-4- yl)azetidin-2-one derivatives (6a-l) was synthesized starting with acetanilide (1). Initially, acetanilide (1) was allowed to react with Vilsmeier-Haack reagent (DMF + POCl 3 ) to form 2- chloro-3-formyl quinoline (2). The 2-chloro-3-formyl quinoline (2) was further treated with p-toluenesulphonic acid and sodium azide which yielded Tetrazolo [1,5-1] quinoline-4- carbaldehyde (3). The reaction of formyl group with various substituted amines (4a-l) formed corresponding Schiff base intermediates (5a-l), which were further allowed to react with chloroacetyl chloride to produce 3-chloro-1-(substituted)-4-(tetrazolo [1,5-a]quinolin-4-yl) azetidin-2-one derivatives (6a-l) . The structure of the final analogues (6a-l) has been con- firmed on the basis of elemental analysis, IR, 1 H NMR, 13 C NMR and mass spectra. All the synthesized compounds were evaluated for their anti-inflammatory and analgesic activities by using carrageenan induced rat paw model and Eddy’s hot plate method respectively. Results: All the values of elemental analysis, IR, 1 H NMR, 13 C NMR and mass spectra were found to be prominent. The anti-inflammatory activity test revealed that 3-chloro-1-(4-metho- xyphenyl)-4-(tetrazolo[1,5-a] quinolin-4-yl)azetidin-2-one (6b), 3-chloro-1-(2-methoxyphe- nyl)-4-(tetrazolo[1,5-a]quinolin-4-yl)azetidin-2-one (6a) exhibited significant anti-inflamma- tory and analgesic activity as compared to control group. Conclusion: The results of the current study indicate that substitution at quinoline derivatives bearing azetidinones scaffolds showed potent analgesic and anti-inflammatory activities. Keywords: Vilsmeier-Haack reaction, Quinoline, Azetidinones, Schiff base, Anti-inflammatory, Analge- sic activity. 1. INTRODUCTION Inflammation is a complex defensive mechanism. During inflammation the body responds to different *Address correspondence to this author at Department of Pharmaceutical Chemistry, Hygia Institute of Pharmaceutical Education and Research, Ghazipur Balram, Ghaila Road Lucknow-206021 India; Tel: +919453409629; Fax: +91-; 52226546437; E-mail: sujeet20gupta2@gmail.com injuries where there is gathering of leukocytes and local fluids which ultimately eliminate the noxious stimulus. The development of persistent damaged tissue is not properly repaired by inflammatory cells in the pathological conditions [1, 2]. During inflammation, some important mediators are re- leased viz. histamine and serotonin. Edema and inflammation have been produced by carrageenan 1875-614X/16 $58.00+.00 © 2016 Bentham Science Publishers Send Orders for Reprints to reprints@benthamscience.ae Anti-Inflammatory & Anti-Allergy Agents in Medicinal Chemistry, 2016, 15, 31-43 31 RESEARCH ARTICLE Synthesis, Characterization & Screening for Anti-Inflammatory & Analgesic Activity of Quinoline Derivatives Bearing Azetidinones Scaffolds