Title:Synthesis, Biological Evaluation and Docking Studies of N-(2-benzamido feruloyl) Aryl Hydrazone Analogues
Volume: 15
Issue: 8
Author(s): M. Soujanya *, G. Rajitha, A. Umamaheswari and K. Sudheer Kumar
Affiliation:
- Department of Chemistry, Gokula Krishna College of Pharmacy, JNTUA, Sullurpeta- 524121, Andhrapradesh,India
Keywords:
Acylhydrazone, docking, antioxidant activity, anti-inflammatory activity, analgesic activity, IC50 value, feruloyl
derivatives.
Abstract: Background: Nowadays inflammation recognized as the underlying basis of number of
diseases but still NSAIDS are the first drugs of choice having several side effects. In addition to that,
oxidative stress also triggers the inflammation. This creates an initiation to introduce new molecules
which act as efficient COX-2 inhibitors with diminished side effects.
Objective: As a part of our search for newer agents, we designed a series of N-acylhydrazones by
combining the pharmacophoric features of hydrazones with feruloyl derivatives in hope of enhancing
the activity profile of title compounds.
Methods: The title compounds (3a-l) were synthesized by the condensation of α-benzamido-(4-
hydroxy-3-methoxy)-cinnamhydrazide (2) with different aromatic aldehydes in acidic conditions and
characterized by elemental, spectral (IR, 1H NMR, 13C NMR, MASS) data and also evaluated for antiinflammatory
(in-vivo, in-vitro and docking), analgesic and antioxidant activities.
Results: The in-vivo anti-inflammatory data revealed that compounds 3j and 3i reduced the edema by
74% and 72% respectively at 100 mg /kg which is comparable to the standard, supported by in-vitro
studies (3j: 10µM and 3i: 16µM as IC50) and also showed good docking scores (3j:-10.28 and 3i:-
10.13). The analgesic activity profile suggested that compounds 3j (65%) and 3e (60%) exhibited good
activity by writhing test. Besides having good anti-inflammatory activity, title compounds also
exhibited appreciable antioxidant potential evaluated by four in-vitro methods. Compounds 3j and 3f
displayed good antioxidant potential than the standard by lipid peroxidation and DPPH scavenging
methods respectively.
Conclusion: Results suggested that the compound 3j emerged as a lead compound having multi target
affinities.
