6'-chloro-6'-cyano-5',6'-dehydro-6'-deoxy-2',3'-O-isopropylidene-N⁶-(4-methyltrityl)-homoadenosine

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 6'-chloro-6'-cyano-5',6'-dehydro-6'-deoxy-2',3'-O-isopropylidene-N⁶-(4-methyltrityl)-homoadenosine
• 英文别名: (E)-3-[(3aR,4R,6R,6aR)-4-[6-[[(4-methoxyphenyl)-diphenylmethyl]amino]purin-9-yl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]-2-chloroprop-2-enenitrile
• 化学式: C₃₅H₃₁ClN₆O₄
• 分子量: 635.122
• InChiKey: RNXJHBSCHMOWRK-NOAUFDKRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  46
• 可旋转键数：
  8
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  116
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  6'-chloro-6'-cyano-5',6'-dehydro-6'-deoxy-2',3'-O-isopropylidene-N⁶-(4-methyltrityl)-homoadenosine 在 甲酸 作用下， 反应 18.0h， 以55%的产率得到(E)-3-[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]-2-chloroprop-2-enenitrile
  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
• 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 、 二甲基亚砜 、 N,N'-二环己基碳二亚胺 作用下， 反应 28.25h， 生成 6'-chloro-6'-cyano-5',6'-dehydro-6'-deoxy-2',3'-O-isopropylidene-N⁶-(4-methyltrityl)-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.