DESIGN, SYNTHESIS, IN VITRO ANTIOXIDANT AND IN VIVO ANTI-INFLAMMATORY ACTIVITIES OF NOVEL OXADIAZOLE DERIVATIVES

  • B. Vishwanathan Department of Pharmaceutical Chemistry, JSS College of Pharmacy, JSS University, Sri Shivarathreeshwara Nagar, Mysore, Karnataka-570 015, India
  • B. M. Gurupadayya Department of Pharmaceutical Chemistry, JSS College of Pharmacy, JSS University, Sri Shivarathreeshwara Nagar, Mysore, Karnataka-570 015, India
  • K. Venkata Sairam Department of Pharmaceutical Chemistry, JSS College of Pharmacy, JSS University, Sri Shivarathreeshwara Nagar, Mysore, Karnataka-570 015, India
  • Bharat Kumar Inturi Department of Pharmaceutical Chemistry, JSS College of Pharmacy, JSS University, Sri Shivarathreeshwara Nagar, Mysore, Karnataka-570 015, India.

Abstract

Objective: In the present study, a series of novel 1,3,4-oxadiazole derivatives (3a-3q) were designed, synthesized and evaluated for antioxidant and anti-inflammatory activities.

Methods: The title compounds were designed and docked onto the COX-2 enzyme (3LN1) protein using SYBYLX 2.1. 2-substituted-5-(5-nitrobenzofuran-2-yl)-1,3,4-oxadiazole derivatives (3a-3p) were synthesized from acid catalyzed dehydrative cyclization of 5-nitrobenzofuran-2-carbohydrazide (2) with various heteroaryl/aryl/aliphatic carboxylic acid derivatives. And 5-(5-nitrobenzofuran-2-yl)-1,3,4-oxadiazole-2-thiol (3q) was synthesized on reacting the hydrazide derivative 2 with carbon disulfide. The synthesized compounds were evaluated for in vitro antioxidant property by DPPH radical scavenging assay method and in vivo anti-inflammatory activity by carrageenan induced paw edema method.

Results: The synthesized 1,3,4-oxadiazole derivatives (3a-3q) were characterized on the basis of LCMS, 1HNMR [13]CNMR, IR and elemental analysis. The title compounds 3a-3q exhibited significant antioxidant efficacy ranging from 34 to 86%and the results of anti-inflammatory evaluation revealed that compounds 3c, 3e and 3d exhibited substantial anti-inflammatory activity of 72, 68 and 65%, respectively, at a dose of 50 mg kg-1.

Conclusion: A significant correlation was observed between the in silico study and the anti-inflammatory results. The anti-inflammatory results highlight the synthesized compounds 3c, 3e and 3d could be considered as possible hit as therapeutic agents.

 

Keywords: Benzofuran, Oxadiazole, Antioxidant, Anti-inflammatory.

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Author Biography

B. Vishwanathan, Department of Pharmaceutical Chemistry, JSS College of Pharmacy, JSS University, Sri Shivarathreeshwara Nagar, Mysore, Karnataka-570 015, India

Lecturer

Dept. of Pharmacutical Chemistry

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Vishwanathan, B., B. M. Gurupadayya, K. V. Sairam, and B. K. Inturi. “DESIGN, SYNTHESIS, IN VITRO ANTIOXIDANT AND IN VIVO ANTI-INFLAMMATORY ACTIVITIES OF NOVEL OXADIAZOLE DERIVATIVES”. International Journal of Pharmacy and Pharmaceutical Sciences, Vol. 6, no. 9, 1, pp. 514-20, https://innovareacademics.in/journals/index.php/ijpps/article/view/2590.
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