Olsuf'eva E N, Rozynov B V
Bioorg Khim. 1990 Jun;16(6):847-53.
Condensation of carminomycin or daunorubicin with glutaric dialdehyde in the presence of NaBH3CN yielded 3'-deamino-3'-piperidinocarminomycin or 3'-deamino-3'-piperidinodaunorubicin and corresponding (13-R, S)-dihydroderivatives. To prepare similar derivatives of 14-hydroxycarminomycin or doxorubicin, 13-dimethylketals of 14-bromocarminomycin or 13-bromodaunorubicin were used in the reaction of reductive alkylation with glutaric or glycolic dialdehyde to give 3'-deamino-3'-piperidino- or 3'-deamino-3'-morpholino derivatives of 13-dimethylketals of 14-bromocarminomycin or daunorubicin, respectively. After deblocking and subsequent hydrolysis of these compounds 3'-deamino-3'-piperidino- and 3'-deamino-3'-morpholino derivatives of 13-hydroxycarminomycin or doxorubicin were prepared. Reduction of the antibiotic derivatives under mass spectrometry conditions was demonstrated.
在NaBH₃CN存在下，柔红霉素或道诺霉素与戊二醛缩合，生成3'-脱氨基-3'-哌啶基柔红霉素或3'-脱氨基-3'-哌啶基道诺霉素以及相应的(13-R, S)-二氢衍生物。为制备14-羟基柔红霉素或阿霉素的类似衍生物，14-溴柔红霉素或13-溴道诺霉素的13-二甲基缩酮用于与戊二醛或乙醇醛进行还原烷基化反应，分别得到14-溴柔红霉素或道诺霉素的13-二甲基缩酮的3'-脱氨基-3'-哌啶基或3'-脱氨基-3'-吗啉代衍生物。在对这些化合物进行脱保护及随后的水解后，制备出了13-羟基柔红霉素或阿霉素的3'-脱氨基-3'-哌啶基和3'-脱氨基-3'-吗啉代衍生物。证明了在质谱条件下抗生素衍生物的还原反应。
