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Sulfonamides and Sulphonyl Ester of Quinolines as Non-Acidic, Non- Steroidal, Anti-inflammatory Agents

[ Vol. 18 , Issue. 2 ]

Author(s):

Bilquees Bano, Kanwal, Khalid Mohammed Khan*, Almas Jabeen, Aisha Faheem, Muhammad Taha, Syed Moazzam Haider and Shahnaz Perveen   Pages 112 - 120 ( 9 )

Abstract:


Background: Quinolines are an important class of heterocyclic compounds possessing a wide range of biological activities. Previously, we had identified Schiff bases of quinoline as potential anti-inflammatory agents, thus the current work is the continuation of our previous study.

Objective: In the current study, 3-, 5-, and 8-sulfonamide and 8-sulfonate derivatives of quinoline (1-50) were synthesized and their anti-inflammatory potential was evaluated. These synthetic analogs were evaluated for their anti-inflammatory activity via ROS (Reactive oxygen species) inhibitory effect produced from phagocytes from human whole blood.

Methods: The sulfonamide and sulfonate derivatives of quinoline were synthesized via treating 5-, 3-, 8-amino, and 8-hydroxy quinolines with different substituted sulfonyl chlorides in pyridine. The synthetic molecules were characterized using various spectroscopic techniques and screened for their anti-inflammatory potential.

Results: Among the synthetic derivatives 1-50, six compounds showed good to moderate antiinflammatory activity. Compounds 47 (IC50 = 2.9 ± 0.5 μg/mL), 36 (IC50 = 3.2 ± 0.2 μg/mL), and 24 (IC50 = 6.7 ± 0.3 μg/mL) exhibited enhanced activity as compared to the standard ibuprofen (IC50 = 11.2 ± 1.9 μg/mL). Compounds 20 (IC50 = 25.5 ± 0.7 μg/mL), 50 (IC50 = 42.9 ± 5.6 μg/mL), and 8 (IC50 = 53.9 ± 3.1 μg/mL) were moderately active, however, rest of the compounds were found to be inactive.

Conclusion: The sulfonamide and sulfonate derivatives of quinoline were found to have promising anti-inflammatory activity. Further studies on the modification of these molecules may lead to the discovery of new and potential anti-inflammatory agents.

Keywords:

Sulfonamide, sulphonyl esters of quinoline, ROS (Reactive oxygen species), whole blood, structure-activity relationship, pyridine.

Affiliation:

H.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, H.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, H.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Dr. Panjwani Center for Molecular Medicine and Drug Research, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Dr. Panjwani Center for Molecular Medicine and Drug Research, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Department of Clinical Pharmacy, Institute for Research and Medical Consultations (IRMC), Imam Abdulrahman Bin Faisal University, P.O. Box 31441, Dammam, H.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, PCSIR Laboratories Complex, Karachi, Shahrah-e-Dr. Salimuzzaman Siddiqui, Karachi 75280

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