Synthesis, molecular modeling, and in vitro screening of monoamine oxidase inhibitory activities of some novel hydrazone derivatives

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Salgin-Goksen U., Gokhan-Kelekci N., Yabanoglu-Ciftci S., Yelekci K., UÇAR G.

JOURNAL OF NEURAL TRANSMISSION, vol.120, no.6, pp.883-891, 2013 (SCI-Expanded)

• Publication Type: Article / Article
• Volume: 120 Issue: 6
• Publication Date: 2013
• Doi Number: 10.1007/s00702-013-0968-2
• Journal Name: JOURNAL OF NEURAL TRANSMISSION
• Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
• Page Numbers: pp.883-891
• Keywords: Hydrazone, 5-methyl-2-benzoxazolinone, Human monoamine oxidase B inhibitors, Molecular docking, B INHIBITORS, ANTIMICROBIAL ACTIVITY, BIOLOGICAL-ACTIVITIES, ANALGESIC ACTIVITY, COUMARIN, DISEASE, MAO
• Hacettepe University Affiliated: Yes

Abstract

Thirteen 2-[2-(5-methyl-2-benzoxazolinone-3-yl)acetyl]-3/4/5-substituted benzylidenehydrazine derivatives were synthesized by reacting 2-(5-methyl-2-benzoxazolinone-3-yl)acetylhydrazine and substituted benzaldehydes in neutral and acid/base catalyzed conditions, and a comparison was made in terms of their yields and reaction times. The structures of all compounds were confirmed by IR, H-1 NMR, C-13 NMR, mass spectral data, and elemental analyses. All the compounds were investigated for their ability to selectively inhibit MAO isoforms by in vitro tests and were found to inhibit recombinant human MAO-B selectively and reversibly in a competitive manner. Among the compounds examined, compound 16 was found to be more selective than selegiline, a known MAO-B inhibitor, in respect to the K (i) values experimentally found. Additionally, compounds 9 and 15 showed moderate MAO-B inhibitor activity. The interaction of compounds with MAO isoforms was investigated by molecular docking studies using recently published crystallographic models of MAO-A and MAO-B. The results obtained from the docking studies were found to be in good agreement with the experimental values.