Gosselin G, Bergogne M C, de Rudder J, De Clercq E, Imbach J L
J Med Chem. 1986 Feb;29(2):203-13. doi: 10.1021/jm00152a007.
The alpha- and beta-D-xylofuranosyl analogues of the naturally occurring nucleosides, as well as other D-xylofuranosyl derivatives, have been the subject of a systematic synthesis and examination of their biological, i.e. antiviral antimetabolic, and cytostatic properties. The beta anomers were prepared by glycosylation of purine and pyrimidine aglycons with peracylated 1-O-acetyl-alpha-D-xylofuranoses, followed by removal of the blocking groups. The alpha anomers were obtained by a multistep synthesis with use of 2-amino- or 2-mercapto-alpha-D-xylofuran[1',2':4,5]-2-oxazoline as starting material. The xylofuranosyl nucleosides were tested for their activity against a variety of RNA and DNA viruses and for inhibition of cell growth and macromolecule synthesis. Three compounds, 9-(beta-D-xylofuranosyl)adenine, 9-(beta-D-xylofuranosyl)guanine, and 1-(beta-D-xylofuranosyl)cytosine, showed marked biological activity.
天然核苷的α-和β-D-木呋喃糖基类似物，以及其他D-木呋喃糖基衍生物，已成为系统合成和研究其生物学性质（即抗病毒、抗代谢和细胞抑制特性）的对象。β-异头物通过嘌呤和嘧啶苷元与全酰化的1-O-乙酰基-α-D-木呋喃糖进行糖基化反应制备，随后去除保护基。α-异头物通过以2-氨基-或2-巯基-α-D-木呋喃[1',2':4,5]-2-恶唑啉为起始原料的多步合成获得。对木呋喃糖基核苷进行了针对多种RNA和DNA病毒的活性测试以及对细胞生长和大分子合成的抑制测试。三种化合物，9-(β-D-木呋喃糖基)腺嘌呤、9-(β-D-木呋喃糖基)鸟嘌呤和1-(β-D-木呋喃糖基)胞嘧啶，表现出显著的生物学活性。
