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

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.