Department of Biochemistry and Biotechnology, Laboratory of Bio-Organic Chemistry, University of Thessaly, 26 Ploutonos Str., 41221 Larissa, Greece.
Department of Chemistry, Aristotle University of Thessaloniki, University Campus, 54124 Thessaloniki, Greece.
Carbohydr Res. 2014 Jan 13;383:50-7. doi: 10.1016/j.carres.2013.11.001. Epub 2013 Nov 9.
A novel series of 2'-spiro pyrimidine pyranonucleosides has been designed and synthesized. Their precursors, 2'-C-cyano nucleosides 5a,b and 6a,b, were obtained by subjecting 1a,b to the sequence of selective protection of the primary hydroxyl group, acetalation, oxidation, and finally treatment with sodium cyanide. Deoxygenation at the 2'-position of cyanohydrins 5a,b or 6a,b led to the 2'-deoxy derivatives 9a,b. Fully deprotection of 5a,b, 6a,b, and 9a,b gave the desired 2'-C-cyano 7a,b, 8a,b, and 2'-C-cyano-2'-deoxy pyranonucleosides 10a,b, respectively. Mesylation of the corresponding cyanohydrins 5a,b and 6a,b afforded compounds 11a,b and 12a,b which after base treatment and subsequent deprotection furnished the spiro nucleosides 15a,b and 16a. The new analogues were evaluated for their potential cytostatic activities in cell culture.
已经设计和合成了一系列新型的 2'-螺嘧啶吡喃核苷。它们的前体，2'-C-氰基核苷 5a,b 和 6a,b，是通过对 1a,b 进行一系列选择性保护伯羟基、缩醛化、氧化，最后用氰化钠处理得到的。氰醇 5a,b 或 6a,b 的 2'-脱氧导致了 2'-脱氧衍生物 9a,b。5a,b、6a,b 和 9a,b 的完全脱保护分别得到了所需的 2'-C-氰基 7a,b、8a,b 和 2'-C-氰基-2'-脱氧吡喃核苷 10a,b。相应的氰醇 5a,b 和 6a,b 的甲磺酸化得到了化合物 11a,b 和 12a,b，它们在碱性条件下处理和随后的脱保护后得到了螺核苷 15a,b 和 16a。新的类似物在细胞培养中评估了它们的潜在细胞抑制活性。
