Synthesis of some novel hydrazone and 2-pyrazoline derivatives: Monoamine oxidase inhibitory activities and docking studies

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Evranos-Aksoz B., Yabanoglu-Ciftci S., UÇAR G., Yelekci K., Ertan R.

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol.24, no.15, pp.3278-3284, 2014 (SCI-Expanded)

• Publication Type: Article / Article
• Volume: 24 Issue: 15
• Publication Date: 2014
• Doi Number: 10.1016/j.bmcl.2014.06.015
• Journal Name: BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
• Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
• Page Numbers: pp.3278-3284
• Hacettepe University Affiliated: Yes

Abstract

A novel series of 2-pyrazoline and hydrazone derivatives were synthesized and investigated for their human monoamine oxidase (hMAO) inhibitory activity. All compounds inhibited the hMAO isoforms (MAO-A or MAO-B) competitively and reversibly. With the exception of 5i, which was a selective MAO-B inhibitor, all derivatives inhibited hMAO-A potently and selectively. According to the experimental K-i values, compounds 6e and 6h exhibited the highest inhibitory activity towards the hMAO-A, whereas compound 5j, which carries a bromine atom at R-4 of the A ring of the pyrazoline, appeared to be the most selective MAO-A inhibitor. Tested compounds were docked computationally into the active site of the hMAO-A and hMAO-B isozymes. The computationally obtained results were in good agreement with the corresponding experimental values. (C) 2014 Elsevier Ltd. All rights reserved.