(E)-4-(adenin-9-yl)-2,3-isopropylidenedioxybutanal oxime

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: (E)-4-(adenin-9-yl)-2,3-isopropylidenedioxybutanal oxime
• 英文别名: (NE)-N-[[(4R,5S)-5-[(6-aminopurin-9-yl)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl]methylidene]hydroxylamine
• 化学式: C₁₂H₁₆N₆O₃
• 分子量: 292.297
• InChiKey: AXQCFZYWFGSMJA-WQXUMDFMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  121
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2',3'-异丙叉腺苷 在 sodium periodate 、 盐酸羟胺 、 sodium methylate 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 甲醇 、 水 、 甲苯 为溶剂， 反应 42.0h， 生成 (E)-4-(adenin-9-yl)-2,3-isopropylidenedioxybutanal oxime
  参考文献：
  名称：

  Synthesis and biological activity of novel S-Adenosyl-l-homocysteine hydrolase inhibitors

  摘要：

  Four potential S-adenosyl-L-homocysteine hydrolase inhibitors were prepared and tested against purified recombinant rat liver enzyme. Preliminary studies indicate that three of these compounds, 1, 2, and 4, caused time-dependent inactivation of S-adenosyl-L-homocysteine hydrolase but showed a biphasic nature. Compound 3 was found to be a rapid equilibrium inhibitor of this enzyme. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00301-8

文献信息

• Novel synthesis of purine acyclonucleosides possessing a chiral 9-hydroxyalkyl group by sugar modification of 9-D-ribitylpurines
  作者：Kosaku Hirota、Yasunari Monguchi、Hironao Sajiki、Magoichi Sako、Yukio Kitade

  DOI：10.1039/a707193k

  日期：——

  A novel approach to the synthesis of purine acyclonucleosides having chiral carbons in the N9-hydroxyalkyl chain was achieved by using 9-(2,3-O-isopropylidene-D-ribityl)purines 1, which are readily prepared from commercially available purine nucleosides. 9-[(2S,3R)-2,3,4-Trihydroxybutyl]purines 4a and 4b, 9-[(2S,3S)-2,3,4-trihydroxybutyl]purines 6a and 6b, L-eritadenine 8, and its analogue 11 are conveniently synthesized via key intermediates, (2S,3S)-2,3-isopropylidenedioxy-4-(purin-9-yl)butanals 2 prepared by NaIO4 oxidation of diols 1.

  利用 9-(2,3-O-异亚丙基-D-核苷)嘌呤 1，合成了一种在 N9-羟基烷基链中具有手性碳的嘌呤无环核苷的新方法，这种嘌呤核苷很容易从市售的嘌呤核苷中制备出来。9-[(2S,3R)-2,3,4-三羟丁基]嘌呤 4a 和 4b、9-[(2S,3S)-2,3,4-三羟丁基]嘌呤 6a 和 6b、L-丝裂腺嘌呤 8、及其类似物 11 可通过关键的中间体（(2S,3S)-2,3-异亚丙基二氧基-4-(嘌呤-9-基)丁醛 2 通过二元醇 1 的 NaIO4 氧化反应制备）方便地合成。
• Synthesis and biological activity of novel S-Adenosyl-l-homocysteine hydrolase inhibitors
  作者：Jennifer A Steere、John F Honek

  DOI：10.1016/s0968-0896(03)00301-8

  日期：2003.7

  Four potential S-adenosyl-L-homocysteine hydrolase inhibitors were prepared and tested against purified recombinant rat liver enzyme. Preliminary studies indicate that three of these compounds, 1, 2, and 4, caused time-dependent inactivation of S-adenosyl-L-homocysteine hydrolase but showed a biphasic nature. Compound 3 was found to be a rapid equilibrium inhibitor of this enzyme. (C) 2003 Elsevier Science Ltd. All rights reserved.