Synthesis, Characterization, in silico and in vivo Evaluation of Amino Acid Derived Schiff Bases of Quinoline- Benzimidazole Hybrids as Anti-epileptic Agents

Indian Journal of Pharmaceutical Education and Research

  • Sonakshi Tyagi1Department of Pharmaceutical Chemistry, Noida Institute of Engineering and Technology (Pharmacy Institute), Knowledge Park-II.
  • Salahuddin Salahuddin1Department of Pharmaceutical Chemistry, Noida Institute of Engineering and Technology (Pharmacy Institute), Knowledge Park-II.
  • Avijit Mazumder1Department of Pharmaceutical Chemistry, Noida Institute of Engineering and Technology (Pharmacy Institute), Knowledge Park-II.
  • Rajnish Kumar1Department of Pharmaceutical Chemistry, Noida Institute of Engineering and Technology (Pharmacy Institute), Knowledge Park-II.
  • Vimal Datt1Department of Pharmaceutical Chemistry, Noida Institute of Engineering and Technology (Pharmacy Institute), Knowledge Park-II.
  • Km. Shabana1Department of Pharmaceutical Chemistry, Noida Institute of Engineering and Technology (Pharmacy Institute), Knowledge Park-II.
  • Abhishek Shankar Sharma1Department of Pharmaceutical Chemistry, Noida Institute of Engineering and Technology (Pharmacy Institute), Knowledge Park-II.
  • Mohamed Jawed Ahsan2Department of Pharmaceutical Chemistry, Maharishi Arvind College of Pharmacy, Ambabari Circle, Jaipur, Rajasthan, INDIA.
  • Mohammad Shahar Yar3Department of Pharmaceutical Chemistry, School of Pharmaceutical Education and Research, Jamia Hamdard, New Delhi, INDIA.

Volume 58 Issue 1s Pages s80-s92

DOI: 10.5530/ijper.58.1s.8

Abstract

Aim/Background: Novel quinoline compounds containing benzimidazole have been synthesized in a number of different ways and screened for anti-epileptic potential through in vivo and in silico studies. Materials and Methods: The novel quinoline-benzimidazole hybrids were synthesized by using substituted carbaldehyde (1,2) and substituted benzimidazole (derived from amino acids) (3a-f ). The synthesized derivatives were characterized by IR, 13C-NMR, 1H-NMR, and Mass spectroscopy and anti-convulsant activity was analyzed by in silico studies on the swiss albino mice using the ScPTZ model. Conclusion and Results: Compounds (1H-Benzoimidazol-2-yl)- substituted-(2-p-tolyloxy-quinolin-3-ylmethylene)-amine (4a-f) and (Benzoimidazol-2-yl)- substituted-(2-ethoxy-quinolin-3-ylmethylene)-amine (5a-f) were synthesized. The synthesized derivatives were characterized (IR, 13C-NMR, 1H-NMR, and mass spectrometry) and screened for their anticonvulsant potentiality by subcutaneous pentylenetetrazol method using carbamazepine. Additionally, the anti-epileptic potential of the produced compounds is confirmed by in silico study results that were obtained. The study also proved that the synthesized derivatives used aminobutyric acid (GABAA) receptors. At a dose level of 30 mg/kg body weight, 4a, 4b, and 4d were found to be more effective than the other synthesized derivatives.

Keywords

  • Seizure
  • Anti-epileptic
  • Quinoline
  • Benzimidazole
  • Subcutaneous pentylenetetrazol
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