基于α-四氢萘酮的钙酮类似物的合成、分子对接和对 MCF-7 乳腺癌细胞的细胞毒性活性

Jurnal Sains dan Kesehatan Pub Date : 2024-02-29 DOI:10.25026/jsk.v6i1.2092

A. Rahmadani, Indriana Tasya, Wahyu Yunita Lestari, Nurdianah Abdul Kadir, Mitha Saputri, Farah Erika, U. Usman, Sukemi Sukemi, Hanggara Arifian, Supriatno Salam, H. Herman, Laode Rijai

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引用次数: 0

摘要

查尔酮化合物是类黄酮和吡唑啉化合物的前体。查尔酮有两个芳香环（A 和 B）和一个不饱和碳原子。查尔酮化合物可通过克莱森-施密特缩合反应合成。查尔酮的合成使用了α-四氢萘酮和苯甲醛类似物的基本成分。在这项研究中，查尔酮的合成在室温下进行了 48 小时。合成材料使用乙醇溶剂和氢氧化钠催化剂，以及基本成分α-四氢萘酮、3,4-二甲氧基苯甲醛和 4-甲氧基苯甲醛。利用光谱方法（包括 1H-NMR、13C-NMR、傅立叶变换红外光谱 (FTIR) 和质谱）对合成化合物进行表征。光谱法表征结果表明，成功合成了两种查尔酮类似化合物，收率均在 70% 以上。这两种查尔酮化合物对 MCF-7 癌细胞的活性较低。分子对接模拟显示，两种查尔酮类似物产生的能级和分子内相互作用均不优于 4-羟基他莫昔芬。关键词：查尔酮类似物 α-四氢萘酮；细胞毒性 AbstrakSenyawa kalkon merupakan salah satu prekursor dari senyawa flavonoid and pirazolina.它含有大量的芳香物质（A 和 B）和大量的原子。通过克莱森-施密特定律，香料可被分解。该化合物可用于生产阿尔法四氢萘酮和苯并二氮杂环胺。在 48 小时内，苏木废墟中的粉末分离器可分离出乙醇和钠盐，以及阿法四环酮、3,4-二甲氧基苯并二氮杂环胺和 4-甲氧基苯并二氮杂环胺。通过 1H-NMR、13C-NMR、傅立叶变换红外光谱（FTIR）和质谱分析仪对样品进行分析。通过使用高光谱分析方法，可对 70% 的模拟粉末进行分析。该研究表明，MCF-7 脂肪库中的高活性模拟白藜芦醇可能会对脂肪库产生影响。模拟分子实验表明，4-噻唑嘧啶类药物可提高能量和分子内相互作用，并与 4-噻唑嘧啶类药物结合。

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Sintesis, Molecular Docking dan Aktivitas Sitotoksik Senyawa Analog Kalkon Berbasis Alfa Tetralone terhadap Sel Kanker Payudara MCF-7

The chalcone compound is a precursor of flavonoid and pyrazoline compounds. Chalcone has two aromatic rings (A and B) and one ?,?-unsaturated carbon atom. Chalcone compounds can be synthesized via the Claisen Schmidt condensation reaction. Chalcone synthesis uses the basic ingredients of alpha tetralone and benzaldehyde analogues. In this research, chalcone synthesis took place for 48 hours at room temperature. Synthetic materials using ethanol solvent and sodium hydroxide catalyst, as well as basic ingredients alpha tetralone, 3,4-dimethoxybenzaldehyde and 4-methoxybenzaldehyde. Characterization of synthesized compounds using spectroscopic methods, including 1H-NMR, 13C-NMR, Fourier Transform Infrared (FTIR) and mass spectroscopy. Characterization results using spectroscopic methods showed that the two chalcone analogue compounds were successfully synthesized with yields above 70%. Both chalcone compounds showed low activity against MCF-7 cancer cells. Molecular docking simulations showed that both chalcone analogues produced energy levels and intramolecular interactions that were no better than 4-hydroxytamoxifen. Keywords: chalcone analogues, alpha tetralone, cytotoxic Abstrak Senyawa kalkon merupakan salah satu prekursor dari senyawa flavonoid dan pirazolina. Kalkon mengandung dua cincin aromatis (A dan B) dan satu atom karbon ?,?-tak jenuh. Senyawa kalkon dapat disintesis melalui reaksi kondensasi Claisen Schmidt. Kalkon disintesis menggunakan bahan dasar alfa tetralone dan analog benzaldehida. Dalam penelitian ini senyawa kalkon disintesis selama 48 jam pada suhu ruang menggunakan pelarut etanol dan katalis natrium hidroksida serta bahan dasar alfa tetralone, 3,4-dimetoksibenzaldehida dan 4-metoksibenzaldehida. Senyawa hasil sintesis dikarakterisasi menggunakan metode spektroskopi meliputi 1H-NMR, 13C-NMR, Fourier Transform Infrared (FTIR) dan spektroskopi massa. Karakterisasi menggunakan metode spektroskopi menunjukkan kedua senyawa analog kalkon berhasil disintesis dengan rendemen diatas 70%. Hasil pengujian sitotoksik menunjukkan bahwa kedua senyawa analog kalkon tidak aktif terhadap sel kanker payudara MCF-7. Simulasi penambatan molekuler menunjukkan bahwa kedua analog kalkon menghasilkan tingkat energi dan interaksi intramolekuler yang tidak lebih baik dibandingkan dengan 4-hidroksitamoksifen. Kata Kunci: analog kalkon, alfa tetralone, sitotoksik

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