(1S,2R,5S)-5-(6-Amino-purin-9-yl)-3-azidomethyl-4-fluoro-cyclopent-3-ene-1,2-diol | 805245-52-7

• 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: (1S,2R,5S)-5-(6-Amino-purin-9-yl)-3-azidomethyl-4-fluoro-cyclopent-3-ene-1,2-diol
• 英文别名: (1S,2R,5S)-5-(6-aminopurin-9-yl)-3-(azidomethyl)-4-fluorocyclopent-3-ene-1,2-diol
• CAS: 805245-52-7
• 化学式: C₁₁H₁₁FN₈O₂
• 分子量: 306.259
• InChiKey: SUJGZFFQZWEGKY-HLTSFMKQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  124
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (1S,2R,5S)-5-(6-Amino-purin-9-yl)-3-azidomethyl-4-fluoro-cyclopent-3-ene-1,2-diol 在 Lindlar's catalyst 氢气 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以96%的产率得到(1S,2R,5S)-3-Aminomethyl-5-(6-amino-purin-9-yl)-4-fluoro-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：

  ((3aS,4S,6aR)-4-(6-amino-9H-purin-9-yl)-5-fluoro-2,2-dimethyl-3a,6a-dihydro-4H-cyclopenta[d][1,3]dioxol-6-yl)methanol 在 sodium azide 、 水 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.33h， 生成 (1S,2R,5S)-5-(6-Amino-purin-9-yl)-3-azidomethyl-4-fluoro-cyclopent-3-ene-1,2-diol
  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.
• STRUCTURE-ACTIVITY RELATIONSHIP OF 5′-SUBSTITUTED FLUORO-NEPLANOCIN A ANALOGUES AS POTENT INHIBITORS OF <i>S</i>-ADENOSYLHOMOCYSTEINE HYDROLASE
  作者：Hyung Ryong Moon、Kang Man Lee、Hyun Joo Lee、Sang Kook Lee、Seung Bin Park、Moon Woo Chun、Lak Shin Jeong

  DOI：10.1081/ncn-200060286

  日期：2005.4.1

  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.