Inamoto Y, Aigami K, Kadono T, Nakayama H, takatsuki A, Tamura G
J Med Chem. 1977 Nov;20(11):1371-4. doi: 10.1021/jm00221a003.
Secondary (6) and tertiary (8) phosphates of exo-5,6-trimethylenenorborn-exo-2-yl alcohol (exo-tricyclo-[5.2.1.0(2,6)]dec-exo-8-yl alcohol, 3) and a secondary ester (9) of a mixture of exo-tricyclo[5.2.1.0(2,6)]dec-3-en-8- and -9-yl alcohol (2) were prepared. The most convenient route to 6 was direct esterification of phosphoric acid with 3. 9 was obtainable by the addition of phosphoric acid to endo-dicyclopentadiene (1). These phosphates were tested in vitro for antiviral activity against Newcastle disease virus using a monolayer culture of chick embryo fibroblasts. 6 was found ca. twice more potent than, while 8 was as active as, amantadine hydrochloride under the present test conditions.
制备了外-5,6-亚甲基降冰片-外-2-醇（外-三环[5.2.1.0(2,6)]癸-外-8-醇，3）的仲（6）和叔（8）磷酸盐以及外-三环[5.2.1.0(2,6)]癸-3-烯-8-醇和-9-醇（2）混合物的仲酯（9）。制备6的最便捷途径是磷酸与3直接酯化。9可通过将磷酸加入内型二环戊二烯（1）获得。使用鸡胚成纤维细胞单层培养物，在体外测试了这些磷酸盐对新城疫病毒的抗病毒活性。在当前测试条件下，发现6的效力约为盐酸金刚烷胺的两倍，而8的活性与盐酸金刚烷胺相当。
