SINTESIS DAN STUDI MOLECULAR DOCKING SENYAWA PIRAZOLIN DAN PIRAZOL TURUNAN 2-HIDROKSIASETOFENON DAN 2-KLOROBENZALDEHID SEBAGAI INHIBITOR ENZIM TIROSINASE
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Date
2021-10
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perpustakaan UR
Abstract
The hyperpigmentation caused by melanin production excessive on the skin. So the prevention of
hyperpigmentation can be done through the use of a cream containing an inhibitor of tyrosinase.
One of the compounds that have activity as inhibitors of the enzyme tyrosinase is pirazolin and
pirazol. Pyrazoline and pyrazole are heterocyclic compounds containing two nitrogen atoms, that
have various activities such as antimicrobial, anticancer, antidiabetic, anti-inflammatory and
tyrosinase inhibitors. Pyrazoline and pyrazole derivatives of 2-hydroxyacetophenone and
2-chlorobenzaldehyde were synthesized through pyrazoline cyclization synthesis and followed by
an oxidative aromatization reaction. The structure of the synthesized compounds were confirmed
through spectroscopic analysis of UV, FTIR, 1H-NMR and HRMS. The yield obtained from the
synthesis of pyrazoline and pyrazole compound were 65,39 % and 26,08 %. Pyrazoline and
pyrazole compounds were tested for their activity as a tyrosinase inhibitor through molecular
docking studies. Molecular docking studies were carried out on the crystal structure of tyrosinase
(PDB ID: 2Y9X) with natural ligands tropolone and kojic acid as positive controls. The docking
results show that the pyrazoline compound has a free bond energy (S score) = -10,5357 kcal/mol
and the pyrazole compound has a bond free energy (S score) = -9,5256 kcal/mol while the free
bond energy for kojic acid as a positive control = -8,8671 kcal/mol. This indicates that the target
compounds of pyrazoline and pyrazole are predicted to be potential tyrosinase enzyme inhibitors.
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Keywords
docking, pyrazole, pyrazoline