S-[2,3,5-tri-O-acetyl-3-C-ethynyl-β-D-ribo-pentofuranosyl]-2-thiocytosine | 848644-48-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: S-[2,3,5-tri-O-acetyl-3-C-ethynyl-β-D-ribo-pentofuranosyl]-2-thiocytosine
• CAS: 848644-48-4
• 化学式: C₁₇H₁₉N₃O₇S
• 分子量: 409.42
• InChiKey: PMXSMYUEPXQUFQ-VWNJHIHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.31
• 重原子数：
  28.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  139.93
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  S-[2,3,5-tri-O-acetyl-3-C-ethynyl-β-D-ribo-pentofuranosyl]-2-thiocytosine 生成 S-[3-C-ethynyl-β-D-ribo-pentofuranosyl]-2-thiocytosine
  参考文献：
  名称：

  SYNTHESIS AND BIOLOGICAL EVALUATION OF CONFORMATIONALLY RESTRICTED AND NUCLEOBASE-MODIFIED ANALOGS OF THE ANTICANCER COMPOUND 3′-C-ETHYNYLCYTIDINE (ECYD)

  摘要：

  A series of conformationally restricted and nucleobase-modified analogs of the anticancer compound 3'-C-ethynylcytidine (ECyd) and its uracil analog (EUrd) have been synthesized While none of,the conformationally restricted analogs displayed anticancer activity, 5-iodo-EUrd and 5-bromo-EUrd displayed potent anticancer activity with IC50 values of 35 nM and 0.73 mu M.

  DOI：

  10.1081/ncn-200059821
• 作为产物：
  描述：

  在 吡啶 、 4-二甲氨基吡啶 、 N,O-双三甲硅基乙酰胺 、 三氟甲磺酸三甲基硅酯 作用下， 以 乙腈 为溶剂， 反应 80.0h， 生成 S-[2,3,5-tri-O-acetyl-3-C-ethynyl-β-D-ribo-pentofuranosyl]-2-thiocytosine
  参考文献：
  名称：

  Synthesis and biological evaluation of nucleobase-modified analogs of the anticancer compounds 3′-C-ethynyluridine (EUrd) and 3′-C-ethynylcytidine (ECyd)

  摘要：

  A series of nucleobase-modified analogs of the anticancer compounds 3'-C-ethynyluridine (EUrd) and 3'-C-ethynylcytidine (ECyd) were designed to overcome the strict substrate specificity of the activating uridine-cytidine kinase. EUrd, ECyd and target nucleosides were obtained using a short convergent synthetic route utilizing diacetone-alpha-D -glucose as starting material. 5-lodo -substituted EUrd was the most potent inhibitor among the novel nucleobase-modified analogs in in vitro assays against human adenocarcinoma breast and prostate cancer cells with IC50 values down to 35 nM. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.11.054