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Synthesis, Structural Characterization and Antinociceptive Activities of New Arylated Quinolines via Suzuki-Miyaura Cross Coupling Reaction

[ Vol. 13 , Issue. 8 ]

Author(s):

Malik A. Ullah, Muhammad Adeel, Muhammad N. Tahir, Abdur Rauf*, Muhammad Akram, Taibi B. Hadda, Yahia N. Mabkhot, Naveed Muhammad, Fehmida Naseer and Mohammad S. Mubarak*   Pages 780 - 786 ( 7 )

Abstract:


Background: The quinoline ring system is one of the most commonly encountered heterocycles in medicinal chemistry, due to the pharmaceutical and medicinal uses of derivatives containing this ring. These quinoline-based compounds have remarkable biological activity, as they are employed as antimalarial, antibacterial, antifungal, and antitumor agents. The quinoline nucleus can be synthesized by various traditional methods such as the Skraup reaction, Friedlaender synthesis, Combes quinoline synthesis, Larock quinoline synthesis, among others.

Methods: The aim of the present work is to synthesize a number of new arylated quninolines having significant antinoceciptive effect through the Suzuki-Miyaura cross coupling reaction using 3- bromoquinoline as a starting material.

Results: A number of new quinoline derivatives have been synthesized. Structures of the newly synthesized compounds were confirmed by means of IR, NMR, and mass spectrometry, and by elemental analysis. In addition, the molecular structures of two representative derivatives were determined with the aid of X-ray crystallography. Additionally, the antinociceptive activity of the prepared compounds was evaluated in vivo; results revealed that most of the tested compounds exhibited a dosedependent antinociceptive effect.

Conclusion: Prepared compounds were found to exhibit significant antinociceptive activities and could be used as potential analgesic agents. Further work, however, may be required to establish the safety and efficacy of these compounds.

Keywords:

Arylated quinolines, antinociceptive activities, mass spectrometry, NMR, suzuki-miyaura cross coupling, X-ray diffraction.

Affiliation:

Institute of Chemical Sciences, Gomal University, D.I. Khan, KPK, Institute of Chemical Sciences, Gomal University, D.I. Khan, KPK, Department of Physics, Sargodha University, Sargodha, Punjab, Department of Chemistry, University of Swabi, Anbar-23561, Khyber Pakhtunkhwa, PCSIR Laboratories Complex, Jamrud Road, Peshwar, KPK, LCM Laboratory, University of Mohamed 1st, Faculty of Sciences, Oujda 60000, Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh-11451, Department of Pharmacy, Hazara University, Mansehra, KPK, Department of Chemistry, Quaid-e-Azam University, Islamabad, Punjab, Department of Chemistry, The University of Jordan, Amman 11942

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