N¹-[(5''-acetoxyethoxy)methyl]-5'-O-tert-butyldimethylsilyl-2',3'-O-isopropylideneinosine | 861656-30-6

• 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: N¹-[(5''-acetoxyethoxy)methyl]-5'-O-tert-butyldimethylsilyl-2',3'-O-isopropylideneinosine
• 英文别名: 2-[[9-[(3aR,4R,6R,6aR)-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-6-oxopurin-1-yl]methoxy]ethyl acetate
• CAS: 861656-30-6
• 化学式: C₂₄H₃₈N₄O₈Si
• 分子量: 538.673
• InChiKey: QNIVXVAMIBWMAI-WGQQHEPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.57
• 重原子数：
  37
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  123
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  N¹-[(5''-acetoxyethoxy)methyl]-5'-O-tert-butyldimethylsilyl-2',3'-O-isopropylideneinosine 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以90%的产率得到N¹-[(5''-acetoxyethoxy)methyl]-2',3'-O-isopropylideneinosine
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Novel Membrane-Permeant Cyclic ADP-Ribose Mimics:  N-[(5‘ ‘-O-Phosphorylethoxy)methyl]-5‘-O-phosphorylinosine 5‘,5‘ ‘-Cyclicpyrophosphate (cIDPRE) and 8-Substituted Derivatives

  摘要：

  N-1- [(5"-O-Phosphorylethoxy)methyl] -5'-O-phosphorylinosine 5',5"-cyclicpyrophosphate (cIDPRE 2a) and the 8-substituted derivatives 8-bromo-, 8-azido-, 8-amino-, and 8-Cl-cIDPRE (2b-e) were synthesized from N1- [(5"-acetoxyethoxy)methyl] -2',3'-O-isopropylideneinosine (5) in good yields. The pharmacological activities of cIDPRE and the 8-substituted derivatives (2a-e) were analyzed in intact and permeabilized. human Jurkat T-lymphocytes. The results indicate that cIDPRE permeates the plasma membrane, releases Ca2+ from an intracellular, cADPR-sensitive Ca2+ store, and subsequently initiates Ca2+ release-activated Ca2+ entry. The Ca2+-releasing activity of cIDPRE was confirmed directly in permeabilized. cells. Using time-resolved confocal Ca2+ imaging at the single cell level, the development of global Ca2+ signals starting from local small Ca2+ signals evoked by cIDPRE was observed. 8-N-3-cIDPRE 2c and 8-NH2-cIDPRE 2d were similarly effective in their agonistic activity as compared to cIDPRE 2a, showing almost indistinguishable concentration-response curves for 2a, 2c, and 2d and very similar kinetics of Ca2+ signaling. In contrast, the halogenated derivatives 8-Br- and 8-Cl-cIDPRE (2b and 2e) did not significantly elevate [Ca2+](i). Therefore, cIDPRE 2a, 8-N-3-cIDPRE 2c, and 8-NH2-cIDPRE 2d are novel membrane permeant cADPR mimic and may provide important novel tools to study cADPR-mediated Ca2+ signaling in intact cells.

  DOI：

  10.1021/jm040092t
• 作为产物：
  描述：

  肌苷 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 对甲苯磺酰氯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 N¹-[(5''-acetoxyethoxy)methyl]-5'-O-tert-butyldimethylsilyl-2',3'-O-isopropylideneinosine
  参考文献：
  名称：

  一种新的合成cADPR类似物的硫取代的环焦磷酸盐的方法

  摘要：

  开发了一种简便高效的合成cIDPRE的硫取代的环焦磷酸盐（PS1-cIDPRE ）的方案。关键步骤是环化过程，该过程由硫取代的环化前体1b通过一锅亚磷酰胺策略完成。

  DOI：

  10.1016/j.cclet.2014.07.010