SINTESIS DAN STUDI MOLECULAR DOCKING SENYAWA 5-(2-2-(MORFOLIN-4-IL)ETOKSI)FENIL- 3-(NAFTALEN-2-IL)-1-FENIL-4,5-1H-PIRAZOL SEBAGAI KANDIDAT OBAT ANTIKANKER PAYUDARA
No Thumbnail Available
Date
2023-09
Authors
Journal Title
Journal ISSN
Volume Title
Publisher
Elfitra
Abstract
Pyrazoline is a five-membered heterocyclic compound containing two adjacent nitrogen
atoms and an endocyclic double bond. This compound is a secondary metabolites,
which exhibits diverse bioactivities, such as antibacterial, anti-inflammatory, antiviral,
antitumor, anticancer, etc. Due to its limited availability in nature, this compound was
imperative to be synthesized for the development of novel pharmaceuticals. A
pyrazoline derivatives substituted with naphthalene and phenoxyethyl morpholine
moiety with named as PRZ-2NFT-2OM was successfully synthesized in three-step of
the reaction process. The initial stage involved the formation of chalcone (3) via the
Claisen-Schmidt condensation reaction. The subsequent stage encompassed the
formation of pyrazoline (5) through the cyclization reaction. The final stage entailed the
fomation of PRZ-2NFT-2OM through O-alkylation of morpholine substituent, with
yields of 31%, 74%, and 51%, respectively. The purity analysis of each synthesized
compound was conducted using techniques such as thin-layer chromatography (TLC),
determination of melting points, and high-performance liquid chromatography (HPLC).
Based on spectroscopy data of UV, FTIR and LC-MS, the PRZ-2NFT-2OM compound
was confirmed to match the intended structure. The PRZ-2NFT-2OM compound
showed remarkable efficacy in in-silico bioactivity analysis through the molecular
docking method as an inhibitor of alpha-estrogen protein (ER-α). It exhibited more
potent values for binding free energy (ΔGbind) and inhibition constant (Ki) than its
positive control which the values were -10.5 kcal/mol and 0.0198 μM for PRZ-2NFT-
2OM, whereas they were -9.5 kcal/mol and 1.27 μM for 4-hydroxytamoxifen.
Description
Keywords
anticancer, morpholine, pyrazoline
Citation
Perpustakaan