Shortnacy-Fowler A T, Tiwari K N, Montgomery J A, Secrist J A
Southern Research Institute, Birmingham, AL 35255-5305, USA.
Nucleosides Nucleotides Nucleic Acids. 2001 Aug;20(8):1583-98. doi: 10.1081/NCN-100105249.
A series of 4'-C-hydroxymethyl-2'-fluoro-D-arabinofuranosylpurine nucleosides was prepared and evaluated for cytotoxicity. The details of a convenient synthesis of the carbohydrate precursor 4-C-hydroxymethyl-3,5-di-O-benzoyl-2-fluoro-alpha-D-arabinofuranosyl bromide (13) are presented. Proof of the structure and configuration at all chiral centers of the sugars and the nucleosides were obtained by proton NMR. All five target nucleosides were evaluated for cytotoxicity in human tumor cell lines. The 4'-C-hydroxymethyl clofarabine analogue (16beta) showed slight cytotoxicity in CCRF-CEM leukemia cells.
制备了一系列4'-C-羟甲基-2'-氟-D-阿拉伯呋喃糖基嘌呤核苷，并对其细胞毒性进行了评估。文中介绍了碳水化合物前体4-C-羟甲基-3,5-二-O-苯甲酰基-2-氟-α-D-阿拉伯呋喃糖基溴（13）简便合成的细节。通过质子核磁共振获得了糖类和核苷所有手性中心的结构和构型证据。对所有五个目标核苷在人肿瘤细胞系中进行了细胞毒性评估。4'-C-羟甲基氯法拉滨类似物（16β）在CCRF-CEM白血病细胞中显示出轻微的细胞毒性。
