Synthesis and molecular modeling studies of naproxen-based acyl hydrazone derivatives

Authors: TUĞBA TAŞKIN TOK, ÖZGÜN ÖZAŞIK, DENİZ SARIGÖL, AYŞE UZGÖREN BARAN

Abstract: A series of N-acylhydrazone derivatives (2a--2p) containing 6-methoxy-naphthalene and acylhydrazone moieties were synthesized in good yield using microwave irradiation and developed as potential COX-2 inhibitors. Furthermore, the interactions between COX-2 and the compounds were examined in detail by molecular modeling studies such as structure--activity relationship and molecular docking performed using Gaussian 09 and Discovery Studio 3.5. As a result, it was found that N-acylhydrazone compounds displayed a different mechanism than SC-558 as COX-2 inhibitor by binding to different active sites of the protein, COX-2. Compound 2c would be a good COX-2 inhibitor candidate for preclinical studies.

Keywords: Naproxen, microwave, acyl hydrazones, molecular docking

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