9-((3aS,4S,6aR)-5-Fluoro-6-fluoromethyl-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-yl)-9H-purin-6-ylamine | 805245-46-9

• 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: 9-((3aS,4S,6aR)-5-Fluoro-6-fluoromethyl-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-yl)-9H-purin-6-ylamine
• CAS: 805245-46-9
• 化学式: C₁₄H₁₅F₂N₅O₂
• 分子量: 323.302
• InChiKey: RRFCRDALFHNVPF-MXWKQRLJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.68
• 重原子数：
  23.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  88.08
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  9-((3aS,4S,6aR)-5-Fluoro-6-fluoromethyl-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-yl)-9H-purin-6-ylamine 在 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 反应 72.0h， 以81%的产率得到(1s,2r,5s)-5-(6-Amino-9h-purin-9-yl)-4-fluoro-3-(fluoromethyl)cyclopent-3-ene-1,2-diol
  参考文献：
  名称：

  Synthesis of 5′-substituted fluoro-neplanocin A analogues: importance of a hydrogen bonding donor at 5′-position for the inhibitory activity of S-adenosylhomocysteine hydrolase

  摘要：

  Four 5'-substituted fluoro-neplanocin A analogues 1a-d were designed and synthesized, using cyclopentenone derivative 2 as a key intermediate. The inhibitory activity against SAH was in the following order: NH2 > SH > F, N-3, indicating a hydrogen bonding donor such as OH or NH2 was essential for inhibitory activity. All the final compounds showed much less decreased cytotoxicity in two cancer cell lines (Col2 and A549), implying that phosphorylation of the 5'-hydroxyl group of fluoro-neplanocin A is closely related to its high cytotoxicity. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.08.047
• 作为产物：
  描述：

  (1S,4R,5S)-1-(6-aminopurine-9-yl)-2-fluoro-4,5-(O-isopropylidenedioxy)-3-(trityloxymethyl)-2-cyclopentene 在 甲醇 、 对甲苯磺酸 、 4,4'-二氨基二苯乙烯-2,2'-二磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 18.5h， 生成 9-((3aS,4S,6aR)-5-Fluoro-6-fluoromethyl-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-yl)-9H-purin-6-ylamine
  参考文献：
  名称：

  STRUCTURE-ACTIVITY RELATIONSHIP OF 5′-SUBSTITUTED FLUORO-NEPLANOCIN A ANALOGUES AS POTENT INHIBITORS OF S-ADENOSYLHOMOCYSTEINE HYDROLASE

  摘要：

  Four 5-substitutedfluoro-neplanocin A analogues 1a-d were designed and synthesized, and the inhibitory activity against SAH was in the following order: NH2 > SH > F, N-3, indicating a hydrogen bonding donor is essential for inhibitory activity.

  DOI：

  10.1081/ncn-200060286