Sriharsha Shimoga Nagaraj, Satish Sridharamurthy, Shashikanth Sheena, Raveesha Koteshwara Anandarao
Department of Studies in Chemistry, University of Mysore, Manasagangothri, Mysore 570 006, India.
Bioorg Med Chem. 2006 Nov 15;14(22):7476-81. doi: 10.1016/j.bmc.2006.07.014. Epub 2006 Aug 4.
The synthesis of a new class of 1,3-thiazolidine nucleoside analogues in which furanose oxygen atom was replaced with nitrogen atom and 2'-carbon atom with sulfur atom is described. N-tert-butoxycarbonyl-2-acyloxy-4-trityloxymethyl-1,3-thiazolidine was coupled with the pyrimidine bases like uracil, thymine, etc. in the presence of lewis acids stannic chloride or trimethyl silyl triflate following Vorbruggen procedure. The antibacterial activity of the novel 1,3-thiazolidine pyrimidine nucleoside analogues is highlighted. All compounds (7a-e) with free NH group in the pyrimidine moiety showed significant biological activity against all the standard strains used and in that compounds 7d and 7e showed significant activity against 14 human pathogens tested.
本文描述了一类新型1,3 - 噻唑烷核苷类似物的合成，其中呋喃糖的氧原子被氮原子取代，2'-碳原子被硫原子取代。N - 叔丁氧羰基 - 2 - 酰氧基 - 4 - 三苯甲基氧甲基 - 1,3 - 噻唑烷在路易斯酸四氯化锡或三甲基甲硅烷基三氟甲磺酸酯存在下，按照Vorbruggen方法与嘧啶碱基如尿嘧啶、胸腺嘧啶等偶联。突出了新型1,3 - 噻唑烷嘧啶核苷类似物的抗菌活性。嘧啶部分带有游离NH基团的所有化合物（7a - e）对所有使用的标准菌株均表现出显著的生物活性，其中化合物7d和7e对所测试的14种人类病原体表现出显著活性。
