3-C-ethynyl-1,2-O-isopropylidene-α-D-ribo-pentodialdo-1,4-furanose | 97694-33-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-C-ethynyl-1,2-O-isopropylidene-α-D-ribo-pentodialdo-1,4-furanose
• CAS: 97694-33-2
• 化学式: C₁₀H₁₂O₅
• 分子量: 212.202
• InChiKey: CSONATNXASNPLM-IBCQBUCCSA-N

物化性质

• 沸点：
  330.6±42.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.57
• 重原子数：
  15.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  64.99
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3-C-ethynyl-1,2-O-isopropylidene-α-D-ribo-pentodialdo-1,4-furanose 在 吡啶 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 N,O-双三甲硅基乙酰胺 、 三氟甲磺酸三甲基硅酯 、 氨 、 三氟乙酸 作用下， 以 甲醇 、 水 、 乙腈 为溶剂， 反应 81.5h， 生成 1-[3-C-ethynyl-β-D-ribo-pentofuranosyl]-6-azauracil
  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
• 作为产物：
  描述：

  1,2-O-isopropylidene-3-C-ethynyl-α-D-allofuranose 在 lead(IV) acetate 作用下， 以 甲苯 为溶剂， 反应 0.5h， 以86%的产率得到3-C-ethynyl-1,2-O-isopropylidene-α-D-ribo-pentodialdo-1,4-furanose
  参考文献：
  名称：

  Synthesis and Conformational Analysis of A Novel Type of Spin Labelled Bicyclonucleoside Based on A Tetrahydrofurano[2,3-c]Pyrrolidine Sugar Skeleton

  摘要：

  Bicyclonucleosides bearing a 5-deoxy-5-N-hydroxyamino-3,N-5-(1,1-ethano)-beta-D-furanosyl sugar moiety (15-18) have been prepared by glycosidation of the corresponding bicyclosugars obtained via an intramolecular reverse Cope elimination. The configuration of the asymmetric carbon of the 1,1-ethano bridge is the most important factor directing the conformation of the N-hydroxypyrrolidine ring and its invertomers ratio as shown by variable temperature H NMR experiments.

  DOI：

  10.1080/07328319808004218

文献信息

• Qureshi, Shireen; Shaw, Gordon, Journal of the Chemical Society. Perkin transactions I, 1985, p. 875 - 882
  作者：Qureshi, Shireen、Shaw, Gordon

  DOI：——

  日期：——
• SYNTHESIS AND BIOLOGICAL EVALUATION OF CONFORMATIONALLY RESTRICTED AND NUCLEOBASE-MODIFIED ANALOGS OF THE ANTICANCER COMPOUND 3′-<i>C</i>-ETHYNYLCYTIDINE (ECYD)
  作者：Patrick J. Hrdlicka、Jan S. Jepsen、Jesper Wengel

  DOI：10.1081/ncn-200059821

  日期：2005.4.1

  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.