9-[(1'R,2'S,3'S,4'R)-2',3'-dihydroxy-4'-fluorocyclopentan-1'-yl]-9H-adenine

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: 9-[(1'R,2'S,3'S,4'R)-2',3'-dihydroxy-4'-fluorocyclopentan-1'-yl]-9H-adenine
• 英文别名: (1S,2S,3R,5R)-3-(6-aminopurin-9-yl)-5-fluorocyclopentane-1,2-diol
• 化学式: C₁₀H₁₂FN₅O₂
• 分子量: 253.236
• InChiKey: AHYAHCRLJXRKDN-APOSLCTFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  110
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (1R,4S)-1-(9-adenyl)-4-hydroxycyclopent-2-ene 在 四氧化锇 、 二乙胺基三氟化硫 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 23.0h， 生成 9-[(1'R,2'S,3'S,4'R)-2',3'-dihydroxy-4'-fluorocyclopentan-1'-yl]-9H-adenine
  参考文献：
  名称：

  4′-Fluorinated carbocyclic nucleosides: Synthesis and inhibitory activity against S-adenosyl-l-homocysteine hydrolase

  摘要：

  4 '-Fluorinated analogue of 9-[(1 ' R,2 ' S,3 ' R)-2 ',3 '-dihydroxy-eyelopentan-1 '-yl]adenine (DHCaA) and their related analogues were systematically synthesized under the Mitsunobu and palladium(O) coupling conditions followed by fluorination with inversion of the configuration by using diethylammosulfur trifluoride, respectively. 4 '-P-Fluoro DHCaA and 2-amino-4 '-alpha-fluoro DHCaA demonstrated slight inhibitory activity against human and Plasmodium falciparum S-adenosyl-L-homocysteine hydrolase, respectively.(c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.04.023

文献信息

• 4′-Fluorinated carbocyclic nucleosides: Synthesis and inhibitory activity against S-adenosyl-l-homocysteine hydrolase
  作者：Yukio Kitade、Takayuki Ando、Tsuyoshi Yamaguchi、Ayumi Hori、Masayuki Nakanishi、Yoshihito Ueno

  DOI：10.1016/j.bmc.2006.04.023

  日期：2006.8

  4 '-Fluorinated analogue of 9-[(1 ' R,2 ' S,3 ' R)-2 ',3 '-dihydroxy-eyelopentan-1 '-yl]adenine (DHCaA) and their related analogues were systematically synthesized under the Mitsunobu and palladium(O) coupling conditions followed by fluorination with inversion of the configuration by using diethylammosulfur trifluoride, respectively. 4 '-P-Fluoro DHCaA and 2-amino-4 '-alpha-fluoro DHCaA demonstrated slight inhibitory activity against human and Plasmodium falciparum S-adenosyl-L-homocysteine hydrolase, respectively.(c) 2006 Elsevier Ltd. All rights reserved.