Casy A F, Dewar G H, Pascoe R A
School of Pharmacy and Pharmacology, University of Bath, Claverton Down, UK.
J Pharm Pharmacol. 1992 Oct;44(10):787-90. doi: 10.1111/j.2042-7158.1992.tb03206.x.
The preparation of some tropane analogues of pethidine and its reversed ester, chiefly with preferred 3 alpha-m-hydroxyphenyl chair conformations, is described. The former were secured from tropan-3-one in a sequence of reactions involving cyanide attack, hydrolysis, Grignard attack and then rearrangements. The reversed ester was obtained by treating tropan-3-one with lithium phenyl, followed by acylation. Configurational and conformational assignments follow from NMR analysis. The antinociceptive potencies of these compounds in mice are reported, and discussed in relation to non-phenolic congeners and the 4-arylpiperidine moiety of morphine.
描述了一些哌替啶及其反式酯的托烷类似物的制备，主要具有优选的3α - 间羟基苯基椅式构象。前者通过一系列反应从托烷 - 3 - 酮获得，这些反应包括氰化物进攻、水解、格氏试剂进攻，然后是重排。反式酯是通过用苯基锂处理托烷 - 3 - 酮，然后进行酰化反应得到的。构型和构象归属来自核磁共振分析。报道了这些化合物在小鼠中的抗伤害感受效力，并与非酚类同系物和吗啡的4 - 芳基哌啶部分相关进行了讨论。
