Methanesulfonic acid (3aR,6S,6aS)-6-(6-amino-purin-9-yl)-5-fluoro-2,2-dimethyl-6,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-ylmethyl ester | 805245-47-0

• 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: Methanesulfonic acid (3aR,6S,6aS)-6-(6-amino-purin-9-yl)-5-fluoro-2,2-dimethyl-6,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-ylmethyl ester
• CAS: 805245-47-0
• 化学式: C₁₅H₁₈FN₅O₅S
• 分子量: 399.403
• InChiKey: NPFIGERPOYNQLL-UTUOFQBUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.68
• 重原子数：
  27.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  131.45
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  Methanesulfonic acid (3aR,6S,6aS)-6-(6-amino-purin-9-yl)-5-fluoro-2,2-dimethyl-6,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-ylmethyl ester 在 水 、 三氟乙酸 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成
  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
• 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 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 18.33h， 生成 Methanesulfonic acid (3aR,6S,6aS)-6-(6-amino-purin-9-yl)-5-fluoro-2,2-dimethyl-6,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-ylmethyl ester
  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

文献信息

• 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
  作者：Hyung Ryong Moon、Hyun Joo Lee、Kyung Ran Kim、Kang Man Lee、Sang Kook Lee、Hea Ok Kim、Moon Woo Chun、Lak Shin Jeong

  DOI：10.1016/j.bmcl.2004.08.047

  日期：2004.11

  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.