2',3'-O-isopropylidene-2-benzyloxymethylinosine | 51554-14-4

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 2',3'-O-isopropylidene-2-benzyloxymethylinosine
• CAS: 51554-14-4
• 化学式: C₂₁H₂₄N₄O₆
• 分子量: 428.445
• InChiKey: NVIDMBZECGQOLO-AEVYOOLXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.25
• 重原子数：
  31.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  120.72
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  2',3'-O-isopropylidene-2-benzyloxymethylinosine 在 吡啶 、 ammonium hydroxide 、 氨 、 N,N-二甲基苯胺 、 三氯氧磷 作用下， 以 异丙醇 、 乙腈 为溶剂， 反应 6.0h， 生成 2',3'-O-isopropylidene-2-benzyloxymethyladenosine
  参考文献：
  名称：

  NAD-based inhibitors with anticancer potential

  摘要：

  Three classes of novel inhibitors of inosine monophosphate dehydrogenase have been prepared and their anti-proliferative properties were evaluated against several cancer cell lines.(1) Mycophenolic adenine dinucleotide analogues (8-13) containing a substituent at the C2 of adenine ring were found to be potent inhibitors of IMPDH (K-i's in range of 0.6-82 nM) and sub-mu M inhibitors of leukemic K562 cell proliferation. (2) Mycophenolic adenosine (D and L) esters (20 and 21) showed a potent inhibition of IMPDH2 (K-i = 102 and K-i = 231 nM, respectively) and inhibition of K562 cell growth (IC50 = 0.5 and IC50 = 1.6 mu M). These compounds serve both as inhibitors of the enzyme and as a depot form of mycophenolic acid. The corresponding amide analogue 22, also a potent inhibitor of IMPDH (K-i = 84 nM), did not inhibit cancer cell proliferation. (3) Mycophenolic-(L)-and (D)-valine adenine diamide derivatives 25 (K-i = 9 nM) and 28 (K-i = 3 nM) were found to be very potent enzymatically, but did not inhibit proliferation of cancer cells. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.11.005
• 作为产物：
  描述：

  苄氧基乙酰氯 在 吡啶 、 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 36.0h， 生成 2',3'-O-isopropylidene-2-benzyloxymethylinosine
  参考文献：
  名称：

  NAD-based inhibitors with anticancer potential

  摘要：

  Three classes of novel inhibitors of inosine monophosphate dehydrogenase have been prepared and their anti-proliferative properties were evaluated against several cancer cell lines.(1) Mycophenolic adenine dinucleotide analogues (8-13) containing a substituent at the C2 of adenine ring were found to be potent inhibitors of IMPDH (K-i's in range of 0.6-82 nM) and sub-mu M inhibitors of leukemic K562 cell proliferation. (2) Mycophenolic adenosine (D and L) esters (20 and 21) showed a potent inhibition of IMPDH2 (K-i = 102 and K-i = 231 nM, respectively) and inhibition of K562 cell growth (IC50 = 0.5 and IC50 = 1.6 mu M). These compounds serve both as inhibitors of the enzyme and as a depot form of mycophenolic acid. The corresponding amide analogue 22, also a potent inhibitor of IMPDH (K-i = 84 nM), did not inhibit cancer cell proliferation. (3) Mycophenolic-(L)-and (D)-valine adenine diamide derivatives 25 (K-i = 9 nM) and 28 (K-i = 3 nM) were found to be very potent enzymatically, but did not inhibit proliferation of cancer cells. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.11.005