Aigami K, Inamoto Y, Takaishi N, Fujikura Y
J Med Chem. 1976 Apr;19(4):536-40. doi: 10.1021/jm00226a018.
New derivatives of 4-homoisotwistane (tricyclo[5.3.1.0(3,8)]undecane) (3), the olefin (8), bromide (4), alcohols (7,9,11, and 14), ketone (10), acid (12), esters (13, 18a, and 18b), amides (5, 16, and 19a-d), nitrile (20), and amines and their hydrochlorides (6, 17, and 21), were prepared, and antiviral activities of these compounds were determined in vitro on a monolayer culture of chick embryo fibroblasts against Newcastle disease virus. 4-Homoisotwist-3-ylamine hydrochloride (6) and 4-homoisotwist-3-ylmethylamine hydrochloride (21) were found 30-50 times more potent than amantadine hydrochloride in this assay. Methods of preparing the test compounds included those functionalization reactions of 3 which revealed many interesting features of the reactivity of the recently discovered polycyclic hydrocarbon 3.
制备了4-高异莰烷（三环[5.3.1.0(3,8)]十一烷）（3）的新衍生物，包括烯烃（8）、溴化物（4）、醇（7、9、11和14）、酮（10）、酸（12）、酯（13、18a和18b）、酰胺（5、16和19a - d）、腈（20）以及胺及其盐酸盐（6、17和21），并在体外针对新城疫病毒在鸡胚成纤维细胞单层培养物上测定了这些化合物的抗病毒活性。在该测定中，发现4-高异莰-3-基胺盐酸盐（6）和4-高异莰-3-基甲胺盐酸盐（21）的效力比盐酸金刚烷胺高30至50倍。制备测试化合物的方法包括3的那些官能化反应，这些反应揭示了最近发现的多环烃3的许多有趣的反应特性。
