JURNAL KIMIA SAINS DAN APLIKASI
Vol 25, No 5 (2022): Volume 25 Issue 5 Year 2022

Synthesis and Tyrosinase Inhibitory Activity of (E)-5-Benzyl-7- (3-Bromobenzylidene)-3-(3-Bromophenyl)-2-Phenyl-3,3a, 4,5,6,7-Hexahydro-2H-Pyrazolo[4,3-c]Pyridine

Nelly Oscifiani (Department of Chemistry, University of Riau, Pekanbaru, Riau|University of Riau|Indonesia)
Noval Herfindo (Sekolah Tinggi Ilmu Farmasi Riau, Pekanbaru, Riau|Sekolah Tinggi Ilmu Farmasi Riau|Indonesia)
Rahayu Rahayu (Department of Chemistry, University of Riau, Pekanbaru, Riau|University of Riau|Indonesia)
Neni Frimayanti (Sekolah Tinggi Ilmu Farmasi Riau, Pekanbaru, Riau|Sekolah Tinggi Ilmu Farmasi Riau|Indonesia)
Adel Zamri (Department of Chemistry, University of Riau, Pekanbaru, Riau|University of Riau|Indonesia)



Article Info

Publish Date
31 May 2022

Abstract

The tyrosinase enzyme plays an essential role in the pigmentation of human skin, fruits, and vegetables. It has been tied with several human skin diseases and post-harvest problems. Hence, the tyrosinase enzyme becomes an excellent therapeutic target to overcome these issues. This study aimed to screen tyrosinase inhibitors by synthesizing halogen-substituted pyrazolopyridine derivatives. The pyrazolopyridine compound was obtained through two stages of synthesis. First, the intermediate compound, a derivative of 3,5-bis(arylidene)-4-piperidone, was synthesized through the Cleisen-Schmidt condensation reaction of 4-piperidone and benzaldehyde derivatives. Furthermore, the intermediate compound was reacted with phenylhydrazine through a cyclocondensation reaction to produce the titled compound with an 11% yield. The chemical structure of the target compound was identified through the interpretation of UV, FTIR, NMR, and HRMS spectra. Then an in vitro assay was conducted on the tyrosinase enzyme of the fungus Agaricus bisporus by detecting the presence of dopachrome at a wavelength of 492 nm. As a result, the in vitro assay showed that the titled compound had a weak inhibitory activity, and the IC50 value was > 500 µM. Thus, the synthesized compound is considered inactive.

Copyrights © 2022






Journal Info

Abbrev

ksa

Publisher

Subject

Chemical Engineering, Chemistry & Bioengineering Chemistry Engineering

Description

urnal Kimia Sains dan Aplikasi (p-ISSN: 1410-8917) and e-ISSN: 2597-9914) is published by Department of Chemistry, Diponegoro University. This journal is published four times per year and publishes research, review and short communication in field of ...