Cannon J G, Hatheway G J
J Med Chem. 1976 Aug;19(8):987-93. doi: 10.1021/jm00230a001.
In a study of conformational requirements for certain dopaminergic agonist molecules, a series of conformationally predictable dopamine congeners related to cis- and trans-octahydrobenzo[f]quinoline was prepared. The complexity and equivocal character of the reduction of variously substituted 4-methyl-1,2,3,4,5,6-hexahydrobenzo[f]quinolines were demonstrated and studied. It was shown that several literature methods for reduction of these systems were in error regarding the stereochemical nature of the product(s). It has been concluded that geometrically specific and predictable reductions of these hexahydrobenzo[f]quinolines seem unlikely to attain, and a plausible rationalization for this conclusion has been proposed. Pharmacologic data on the compounds prepared are consistent with our earlier proposals of a biologically significant conformation of dopamine for emesis, the pecking syndrome in pigeons, and other physiological effects.
在一项关于某些多巴胺能激动剂分子构象要求的研究中，制备了一系列与顺式和反式八氢苯并[f]喹啉相关的构象可预测的多巴胺同系物。研究并证明了各种取代的4-甲基-1,2,3,4,5,6-六氢苯并[f]喹啉还原反应的复杂性和不确定性。结果表明，文献中几种还原这些体系的方法在产物的立体化学性质方面存在错误。得出的结论是，这些六氢苯并[f]喹啉的几何特异性和可预测的还原似乎不太可能实现，并为此结论提出了一个合理的解释。所制备化合物的药理数据与我们早期提出的多巴胺在呕吐、鸽子啄癖综合征及其他生理效应方面具有生物学重要构象的观点一致。
