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

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

Volume: 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*

Affiliation:

• Department of Chemistry, University of Swabi, Anbar-23561, Khyber Pakhtunkhwa,Pakistan

• Department of Chemistry, The University of Jordan, Amman 11942,Jordan

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

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.

Cite this article as:

Ullah A. Malik , Adeel Muhammad , Tahir N. Muhammad, Rauf Abdur *, Akram Muhammad , Hadda B. Taibi , Mabkhot N. Yahia , Muhammad Naveed , Naseer Fehmida and Mubarak S. Mohammad *, Synthesis, Structural Characterization and Antinociceptive Activities of New Arylated Quinolines via Suzuki-Miyaura Cross Coupling Reaction, Medicinal Chemistry 2017; 13 (8) . https://dx.doi.org/10.2174/1573406413666170704100611