Shiotani S, Kometani T
J Med Chem. 1976 Jun;19(6):803-6. doi: 10.1021/jm00228a013.
Six 10-hydroxy-4-methyl-2,3,4,5,6,7-hexahydro-1,6-methano-1H-4-benzazonine derivatives 17a-f have been synthesized as potential analgesics. The synthesis of these compounds involved conversion of 4-(2-dimethylaminoethyl)-6-methoxy alpha tetralone derivatives 12a-f to their N-methyl analogues and the subsequent intramolecular mannich reaction with formaldehyde to give the 7-keto C-ring homobenzomorphans 14a-f from which 17a-f, respectively, were obtained. Compounds 17a-f are as potent as morphine as analgesics (mice).
已合成了六种10-羟基-4-甲基-2,3,4,5,6,7-六氢-1,6-亚甲基-1H-4-苯并吖庚因衍生物17a-f作为潜在的镇痛药。这些化合物的合成包括将4-(2-二甲基氨基乙基)-6-甲氧基α-四氢萘酮衍生物12a-f转化为它们的N-甲基类似物，随后与甲醛进行分子内曼尼希反应，得到7-酮基C环高苯并吗啡烷14a-f，分别从中得到17a-f。化合物17a-f作为镇痛药（小鼠）与吗啡效力相当。
