SINTESIS DAN STUDI IN SILICO SENYAWA PIRAZOLIN 2-(5-4- KLOROFENIL)-1-FENIL-4,5-DIHIDRO-1H-PIRAZOL-3-IL)NAFTALEN- 1-OL SEBAGAI KANDIDAT ANTIKANKER PAYUDARA
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Date
2023-09
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Elfitra
Abstract
Pyrazoline is a pentacyclic heterocyclic compound having two adjacent nitrogen atoms
and an endocyclic double bond. Pyrazoline is known to have various biological
activities, one of which is anticancer. Pyrazoline 2-(5-4-chlorophenyl)-1-phenyl-4,5-
dihydro-1H-pyrazol-3-yl)naphthalene-1-ol has been successfully synthesized through
two stages of reaction. The first step begins with the formation of chalcone 3-(4-
chlorophryl)1-(1-hydroxynaphthalene-2-yl)-2-propen-1-one by reacting 1-hydroxy-2-
acetylnaphthalene and 4-chlorobenzaldehyde via Claisen-Schmidt condensation with a
yield of 54%. The second stage was followed by reacting the synthesized chalcone
compound with phenyl hydrazine using sodium hydroxide catalyst (pellets). The target
compound synthesis method is heating a thick glass tube at a temperature of 70-80oC
with a yield of 82%. The purity of the target compound was determined using Thin
Layer Chromatography (TLC), melting point, and High Performance Liquid
Chromatography (HPLC) analysis, then the chemical structure was confirmed through
Ultraviolet (UV) spectroscopy, Fourier Transform Infra Red (FTIR), and Liquid
Chromatography Mass Spectrometry (LC-MS) analysis. The results of molecular
docking of PF-NH1-4Cl compound against α estrogen receptors have a binding free
energy (ΔGbind) value of -9.3 kcal/mol and inhibition constant (Ki) = 1.49 nM.
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Keywords
anticancer, chalcone, pyrazoline
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