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

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Tok T. T., OZASIK O., Sarigol D., Baran A. U.

TURKISH JOURNAL OF CHEMISTRY, cilt.39, sa.1, ss.64-83, 2015 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 39 Sayı: 1
  • Basım Tarihi: 2015
  • Doi Numarası: 10.3906/kim-1401-91
  • Dergi Adı: TURKISH JOURNAL OF CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, TR DİZİN (ULAKBİM)
  • Sayfa Sayıları: ss.64-83
  • Hacettepe Üniversitesi Adresli: Evet

Özet

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.