Obregón-Mendoza Marco A, Estévez-Carmona María Mirian, Hernández-Ortega Simón, Soriano-García Manuel, Ramírez-Apan María Teresa, Orea Laura, Pilotzi Hugo, Gnecco Dino, Cassani Julia, Enríquez Raúl G
Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, México, D.F. C.P. 04510, Mexico.
Centro de Química, Benemérita Universidad Autónoma de Puebla, Puebla C.P. 72570, Mexico.
Molecules. 2016 Dec 29;22(1):33. doi: 10.3390/molecules22010033.
Curcumin and its derivatives have been extensively studied for their remarkable medicinal properties, and their chemical synthesis has been an important step in the optimization of well-controlled laboratory production. A family of new compounds that mimic the structure of curcumin and curcuminoids, here named -curcuminoids (-), was synthesized and characterized using 1D ¹H- and C-NMR, IR, and mass spectrometry; the X-ray structure of , , , , , , and are reported here for the first time. The main structural feature of these compounds is the reverse linkage of the two aromatic moieties, where the acid chloride moiety is linked to the phenolic group while preserving α, β-unsaturated ketone functionality. The cytotoxic screening of , , , and at 50 and 10 µg/mL was carried out with human cancer cell lines K562, MCF-7, and SKLU-1. Lipid peroxidation on rat brain was also tested for compounds and . Compounds , , and showed relevant cytotoxic activity against these cancer cell lines, and showed a protective effect against lipid peroxidation. The molecular resemblance to curcuminoids and analogs with substituents suggests a potential source of useful bioactive compounds.
姜黄素及其衍生物因其显著的药用特性而受到广泛研究，其化学合成是优化实验室精确生产的重要一步。合成了一类模拟姜黄素和姜黄素类似物结构的新化合物，在此命名为β-姜黄素类似物（β-），并使用一维¹H-和¹³C-NMR、红外光谱和质谱对其进行了表征；首次报道了β-、β-、β-、β-、β-、β-和β-的X射线结构。这些化合物的主要结构特征是两个芳香部分的反向连接，其中酰氯部分与酚羟基相连，同时保留α,β-不饱和酮官能团。用人类癌细胞系K562、MCF-7和SKLU-1对β-、β-、β-和β-在50和10μg/mL浓度下进行了细胞毒性筛选。还对化合物β-和β-进行了大鼠脑脂质过氧化测试。化合物β-、β-和β-对这些癌细胞系显示出相关的细胞毒性活性，并且β-对脂质过氧化具有保护作用。与姜黄素类似物和具有β-取代基的类似物的分子相似性表明了有用生物活性化合物的潜在来源。
