(Z)-6'-chloro-6'-cyano-5',6'-dehydro-6'-deoxy-homoadenosine

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 5'-脱氧核糖核苷
• 英文名称: (Z)-6'-chloro-6'-cyano-5',6'-dehydro-6'-deoxy-homoadenosine
• 英文别名: (Z)-3-[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]-2-chloroprop-2-enenitrile
• 化学式: C₁₂H₁₁ClN₆O₃
• 分子量: 322.711
• InChiKey: ZAPJLOZDFXAJAJ-VNIYPCIQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  143
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2',3'-异丙叉腺苷 在 吡啶 、 二氯乙酸 、 三甲基氯硅烷 、 甲酸 、 二甲基亚砜 、 N,N'-二环己基碳二亚胺 作用下， 反应 48.25h， 生成 (Z)-6'-chloro-6'-cyano-5',6'-dehydro-6'-deoxy-homoadenosine
  参考文献：
  名称：

  Inactivation of S-Adenosyl-l-homocysteine Hydrolase by 6‘-Cyano-5‘,6‘-didehydro- 6‘-deoxyhomoadenosine and 6‘-Chloro-6‘- cyano-5‘,6‘-didehydro-6‘-deoxyhomoadenosine. Antiviral and Cytotoxic Effects

  摘要：

  6'-Cyano-5',6'-didehydro-6'-deoxyhomoadenosine (E)-1, (Z)-1, and 6'-chloro-6'-cyano-5',6'-didehydro-6'-deoxyhomoadenosine (E)-2 were synthesized and tested as new mechanism-based inhibitors of AdoHcy hydrolase. Nucleoside (E)-1 was identified as a type I inhibitor of the enzyme, whereas inactivation of the enzyme by nucleosides (Z)-1 and (E)-2 was accompanied by the formation of a covalent labeling of AdoHcy hydrolase.

  DOI：

  10.1021/jm051023x

文献信息

• Inactivation of <i>S</i>-Adenosyl-<scp>l</scp>-homocysteine Hydrolase by 6‘-Cyano-5‘,6‘-didehydro- 6‘-deoxyhomoadenosine and 6‘-Chloro-6‘- cyano-5‘,6‘-didehydro-6‘-deoxyhomoadenosine. Antiviral and Cytotoxic Effects
  作者：Georges Guillerm、Murielle Muzard、Cédric Glapski、Serge Pilard、Erik De Clercq

  DOI：10.1021/jm051023x

  日期：2006.2.1

  6'-Cyano-5',6'-didehydro-6'-deoxyhomoadenosine (E)-1, (Z)-1, and 6'-chloro-6'-cyano-5',6'-didehydro-6'-deoxyhomoadenosine (E)-2 were synthesized and tested as new mechanism-based inhibitors of AdoHcy hydrolase. Nucleoside (E)-1 was identified as a type I inhibitor of the enzyme, whereas inactivation of the enzyme by nucleosides (Z)-1 and (E)-2 was accompanied by the formation of a covalent labeling of AdoHcy hydrolase.