Skolkovo Institute of Science and Technology, Nobel St. 3, Moscow, 143026, Russia.
INEOS RAS, Vavilova St. 28, B-334, Moscow, 119991, Russia.
Org Biomol Chem. 2020 Nov 4;18(42):8702-8708. doi: 10.1039/d0ob01826k.
Here we report the Friedel-Crafts arylation of chlorofullerenes C60Cl6 and C70Cl8 with thiophene-based methyl esters. While C60Cl6 formed expected Cs-C60R5Cl products, C70Cl8 demonstrated a tendency for both substitution of chlorine atoms and addition of an extra thiophene unit, thus forming Cs-C70R8 and C1-C70R9H compounds. The synthesized water-soluble C60 and C70 fullerene derivatives with thiophene-based addends demonstrated high activity against a broad range of viruses, including human immunodeficiency virus, influenza virus, cytomegalovirus, and herpes simplex virus. The record activity of C70 fullerene derivatives against herpes simplex virus together with low toxicity in mice makes them promising candidates for the development of novel non-nucleoside antiherpetic drugs.
在这里，我们报告了用噻吩基甲酯对氯 fullerene C60Cl6 和 C70Cl8 的 Friedel-Crafts 芳基化反应。虽然 C60Cl6 形成了预期的 Cs-C60R5Cl 产物，但 C70Cl8 表现出取代氯原子和添加额外噻吩单元的倾向，从而形成了 Cs-C70R8 和 C1-C70R9H 化合物。合成的具有噻吩基加合物的水溶性 C60 和 C70 富勒烯衍生物对广泛的病毒具有高活性，包括人类免疫缺陷病毒、流感病毒、巨细胞病毒和单纯疱疹病毒。C70 富勒烯衍生物对单纯疱疹病毒的高活性以及在小鼠中的低毒性使它们成为开发新型非核苷类抗疱疹药物的有前途的候选物。
