Yilmaz Raşit Fikret, Erkan Sultan, Ökten Salih, Tutar Ahmet, Şahin Ertan
Department of Fundamental Sciences, National Defence University, Turkish Naval Academy, İstanbul, Turkiye.
Department of Chemistry, Faculty of Science, Sivas Cumhuriyet University, Sivas, Turkiye.
Turk J Chem. 2023 Oct 11;47(6):1459-1478. doi: 10.55730/1300-0527.3628. eCollection 2023.
In this study, a new method for synthesizing diepoxides is proposed. Tetrahydroindene was brominated with NBS in the presence of LiClO and acetic acid, resulting in the formation of dibromodiacetate derivatives and . Treatment of compounds and with NaOH in methanol produced a mixture of diepoxides and . Additionally, direct bromination of tetrahydro-1H-indene yielded tetrabromo octahydroindene isomers and . The structures of the compounds were characterized using spectroscopic techniques such as H NMR, C NMR, APT, COSY, and XRD. The new method provides an easy and selective route to access epoxides for the synthesis of various chemicals. This study also highlights the selective formation of endo-exo and exo-exo orientations of the obtained diepoxides, distinguishing it from previous studies. The stability and properties of the stereoisomers were investigated using computational methods, revealing the most stable configurations. Reactive sites in the molecules were identified using contour diagrams and molecular electrostatic potential maps. The anticancer properties of the compounds were evaluated in silico, comparing them to 5-fluorouracil (5-FU) against several cancer cell lines. The compounds exhibited the most effective anticancer activity against MCF-7 cells, with the order of anticancer activities generally determined as > > > > > > 5-FU.
在本研究中，提出了一种合成双环氧化合物的新方法。四氢茚在高氯酸锂和乙酸存在下用N-溴代丁二酰亚胺进行溴化反应，生成二溴二乙酸酯衍生物和。化合物和在甲醇中用氢氧化钠处理得到双环氧化合物和的混合物。此外，四氢-1H-茚的直接溴化反应生成四溴八氢茚异构体和。使用诸如氢核磁共振、碳核磁共振、无畸变极化转移增强法、同核去偶相关谱和X射线衍射等光谱技术对化合物的结构进行了表征。该新方法为合成各种化学品提供了一条简便且具有选择性的获取环氧化合物的途径。本研究还突出了所得到的双环氧化合物内-外和外-外取向的选择性形成，这使其有别于先前的研究。使用计算方法研究了立体异构体的稳定性和性质，揭示了最稳定的构型。利用等高线图和分子静电势图确定了分子中的反应位点。在计算机模拟中评估了这些化合物的抗癌特性，并将它们与5-氟尿嘧啶（5-FU）针对几种癌细胞系进行了比较。这些化合物对MCF-7细胞表现出最有效的抗癌活性，抗癌活性顺序通常确定为>>> >>> >>> 5-FU。
