Ruszkowska Joanna, Chrobak Robert, Zero Paweł, Maurin Jan K, Szawkało Joanna, Czarnocki Zbigniew
Faculty of Chemistry, Warsaw University, Warszawa, Poland.
Acta Biochim Pol. 2007;54(4):857-61. Epub 2007 Dec 8.
Vindoline and its analogues are important constituents of the Madagascan periwinkle Catharanthus roseus, and some of them are valuable chemotherapy drugs used in treatment for some types of cancer, including leukaemia, lymphoma, breast and lung cancer. The search for semi-synthetic congeners of natural substances is still an important task for organic chemistry. In this communication we report the synthesis of five new vindoline derivatives, 15-(2-methoxyphenyl)vindoline 11, 15-(3-methoxyphenyl)vindoline 12, 15-(2-nitrophenyl)vindoline 13, 15-(3-cyanophenyl)vindoline 15, and 15-(4-cyanophenyl)vindoline 16 using the Suzuki-Miyaura reaction as the key step. X-Ray analysis of compound 16 is also reported.
长春质碱及其类似物是马达加斯加长春花（Catharanthus roseus）的重要成分，其中一些是用于治疗某些类型癌症（包括白血病、淋巴瘤、乳腺癌和肺癌）的有价值的化疗药物。寻找天然物质的半合成类似物仍然是有机化学的一项重要任务。在本通讯中，我们报道了以铃木-宫浦反应为关键步骤合成的五种新的长春质碱衍生物，即15-（2-甲氧基苯基）长春质碱11、15-（3-甲氧基苯基）长春质碱12、15-（2-硝基苯基）长春质碱13、15-（3-氰基苯基）长春质碱15和15-（4-氰基苯基）长春质碱16。还报道了化合物16的X射线分析结果。
