Synthesis of benzoyl hydrazones having 4-hydroxy-3,5-dimethoxy phenyl ring, their biological activities, and molecular modeling studies on enzyme inhibition activities

Kursun Aktar B. S., Sicak Y., TATAR YILMAZ G., Oruc-Emre E. E.

TURKISH JOURNAL OF CHEMISTRY, vol.46, pp.236-252, 2022 (SCI-Expanded) identifier identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 46
  • Publication Date: 2022
  • Doi Number: 10.3906/kim-2107-7
  • Journal Name: TURKISH JOURNAL OF CHEMISTRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chemical Abstracts Core, TR DİZİN (ULAKBİM)
  • Page Numbers: pp.236-252
  • Keywords: Benzoyl hydrazone, antioxidant activity, anticholinesterase enzyme inhibitory activity, tyrosinase enzyme inhibition activity, urease enzyme inhibition activity, molecular docking, TYROSINASE INHIBITORS, ANTIOXIDANT ACTIVITY, ACETYLCHOLINESTERASE, DERIVATIVES, MECHANISM, DISEASE, ACID, SKIN
  • Karadeniz Technical University Affiliated: Yes

Abstract

Hydrazone compounds such as anticholinesterase, tyrosinase, and urease have high capacity in terms of antioxidant activity and enzyme inhibition activities. In this study, benzoyl hydrazones compounds (7a-7m) were synthesized starting from 3,5-dimethoxy4-hydroxybenzaldehyde. Antioxidant activity of the synthesized compounds was evaluated. In the beta-carotene-linoleic acid and ABTS cation radical scavenging activities, compounds 7j, 7e, and 7m stand out as the most active compounds, respectively. In the anticholinesterase enzyme inhibition activity results, compound 7f exhibited the best activity against AChE and BChE enzymes in the synthesis series. In addition, molecular docking analysis was performed to understand the inhibition mechanism of the synthesized compounds with target enzymes at the atomic level. In the light of biological activity and in silico studies, it has the potential to guide clinical studies for the development of new drugs for Alzheimer disease in the future.