Synthesis and biological studies of 3-(.beta.-D-ribofuranosyl)-2,3-dihydro-6H-1,3-oxazine-2,6-dione, a new pyrimidine nucleoside analog related to uridine
作者:Tek-Ling Chwang、William F. Wood、J. Rodney Parkhurst、Stephen Nesnow、Peter V. Danenberg、Charles Heidelberger
DOI:10.1021/jm00227a013
日期:1976.5
5-tri-O-(2,2,2-trichloroethoxycarbonyl)ribofuranose, gave, on removal of the protecting groups with zinc dust,3-(beta-d-ribofuranosyl)-2,3-dihydro-6H-1,3-oxazine-2,6-dione (1). The structure of 1 was confirmed by uv, ir, NMR, and CD spectral data and was shown to be an N nucleoside. Uracil anhydride, 2, and, to a lesser extent, its ribonucleoside 1 exert a moderate growth inhibition of mouse leukemia L5178Y
在氯化锡存在下,2,3-二氢-6H-1,3-恶嗪-2,6-二酮的三甲基甲硅烷基衍生物(2,“尿嘧啶酐”)与被保护的1-O-乙酰基呋喃核糖核酸酶反应得到相应的嵌段核苷。3-(2,3-5-Tri-O-2',2',2'-三氯乙氧基羰基-β-d-呋喃呋喃糖基)-2,3-二氢-6H-1,3-恶嗪-2,6-二酮由受保护的糖3c如此制得的(4c)1-O-乙酰基-2,3,5-三-O-(2,2,2-三氯乙氧基羰基)核呋喃糖,用锌粉除去保护基后,得到: 3-(β-d-呋喃核糖基)-2,3-二氢-6H-1,3-恶嗪-2,6-二酮(1)。1的结构通过uv,ir,NMR和CD光谱数据确定,并显示为N核苷。尿嘧啶酐2及其较小程度的核糖核苷1对小鼠白血病L5178Y,HeLa,和Novikoff肝癌细胞的培养。两种化合物均对HeLa细胞中的痘苗病毒复制产生微弱的抑制作用。