Synthesis, Spectral Analysis, DFT and Molecular docking studies of Some Novel Oxime Derivatives

Abstract

A series of novel Di‑tert‑butyl(E)-4‑hydroxy-6-(hydroxyimino)-4-methyl-2-arylcyclohexane-1,3-dicarboxylate derivatives were synthesized in two steps with excellent yields. In the First step, tert‑butylacetoacetate and substituted benzaldehyde were directly condensed using methylamine catalyst in ethanol as a solvent to create substituted 1,3-bis(tert‑butoxycarbonyl)-cyclohexanone. A second stage involved synthesizing BHMAC (Ar = pH and Ar = p-OCH3C6H4) by treating the respective ketones in an ethanol medium with hydroxylamine hydrochloride and sodium acetate trihydrate. NMR, IR, and mass spectroscopy were used to confirm the oxime derivatives. Density functional theory calculations at the DFT/B3LYP level using 6–31G++ (d, p) have been performed to reproduce the structure and geometry in order to understand the electrical behavior of synthesized compounds. Using bovine serum albumin, a protein denaturation test is used to assess anti-inflammatory efficacy. BHMAC demonstrates conventional pharmacological molecules in its notable anti-inflammatory action and has effects that are dependent on concentration. Utilizing the phosphomolybdenum technique, the total antioxidant activity of the 2,4-bis(tert‑butoxycarbonyl)-cyclohexanone oxime (2 a and 2 b) was assessed standard Vitamin C medications .The results revealed that 2 a & 2 b possess significant antioxidant activity Molecular docking experiments indicate that the chemical may interact with anti-inflammatory and antioxidant causing enzymes. Strong binding energies and inhibition constants with cyclooxygenase (PDB: 1PGG) are demonstrated by BHMAC, suggesting that it is a suitable material for investigations pertaining to anti-inflammatory. BHMAC's remarkable anti-inflammatory and antioxidant properties, together with its synthesis and characterization, highlight its potential as a viable candidate for more biomedical research and therapeutic development.