(1S,2R,3S,4R)-4-(6-Amino-2-fluoro-purin-9-yl)-cyclopentane-1,2,3-triol | 640720-56-5

• 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,3S,4R)-4-(6-Amino-2-fluoro-purin-9-yl)-cyclopentane-1,2,3-triol
• 英文别名: 2-Fluoronoraristeromycin；(1S,2R,3S,4R)-4-(6-amino-2-fluoropurin-9-yl)cyclopentane-1,2,3-triol
• CAS: 640720-56-5
• 化学式: C₁₀H₁₂FN₅O₃
• 分子量: 269.235
• InChiKey: AJVKXNXJKJUXAE-LPWJYYESSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  19
• 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：
  130
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  原甲酸三乙酯 、 (1S,2R,3S,4R)-4-(6-Amino-2-fluoro-purin-9-yl)-cyclopentane-1,2,3-triol 在 对甲苯磺酸 作用下， 以 丙酮 为溶剂， 反应 1.0h， 以97%的产率得到9-[(1R,2S,3R,4S)-4-hydroxy-2,3-O-isopropylidenecyclopentan-1-yl]-9H-2-fluoroadenine
  参考文献：
  名称：

  Synthesis of 3′,4′-epoxynoraristeromycin analogs for molecular labeling probe of S-adenosyl-l-homocysteine hydrolase

  摘要：

  3',4'-Epoxynoraristeromycin analogs were designed and synthesized. Their affinities with human and Plasmodium falciparum S-adenosyl-L-homo-cysteine hydrolase were investigated. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.05.020
• 作为产物：
  描述：

  2-氟-6-氨基嘌呤 在 四氧化锇 、 四(三苯基膦)钯 、 N-甲基吲哚酮 、 水 、 sodium hydride 、 二甲基亚砜 作用下， 以 四氢呋喃 为溶剂， 生成 (1S,2R,3S,4R)-4-(6-Amino-2-fluoro-purin-9-yl)-cyclopentane-1,2,3-triol
  参考文献：
  名称：

  Synthesis of 2-fluoronoraristeromycin and its inhibitory activity against Plasmodium falciparum S-Adenosyl-l-homocysteine hydrolase

  摘要：

  Palladium-coupling reaction of (IS, 4 R)-cis-4-acetoxy-2-cyclopenten-1-ol with sodium salt of 2-fluoroadenine resulted in the formation of (IS,4R)-4-(6-amino-2-fluoro-9H-purin-9-yl)cyclopent-2-en-1-ol. Subsequent oxidation was carried out with osmium tetraoxide (OsO4) in the presence of 4-methylmorpholine N-oxide (NMO) to give 2-fluoronoraristeromycin, possessing significant inhibitory activity against recombinant Plasm odium falciparum SAH hydrolase. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.08.074

文献信息

• Synthesis of 2-fluoronoraristeromycin and its inhibitory activity against Plasmodium falciparum S-Adenosyl-l-homocysteine hydrolase
  作者：Yukio Kitade、Hiroharu Kojima、Fazila Zulfiqur、Hye-Sook Kim、Yusuke Wataya

  DOI：10.1016/j.bmcl.2003.08.074

  日期：2003.11

  Palladium-coupling reaction of (IS, 4 R)-cis-4-acetoxy-2-cyclopenten-1-ol with sodium salt of 2-fluoroadenine resulted in the formation of (IS,4R)-4-(6-amino-2-fluoro-9H-purin-9-yl)cyclopent-2-en-1-ol. Subsequent oxidation was carried out with osmium tetraoxide (OsO4) in the presence of 4-methylmorpholine N-oxide (NMO) to give 2-fluoronoraristeromycin, possessing significant inhibitory activity against recombinant Plasm odium falciparum SAH hydrolase. (C) 2003 Elsevier Ltd. All rights reserved.
• Synthesis of 3′,4′-epoxynoraristeromycin analogs for molecular labeling probe of S-adenosyl-l-homocysteine hydrolase
  作者：Hiroharu Kojima、Atsushi Kozaki、Masafumi Iwata、Takayuki Ando、Yukio Kitade

  DOI：10.1016/j.bmc.2008.05.020

  日期：2008.7.1

  3',4'-Epoxynoraristeromycin analogs were designed and synthesized. Their affinities with human and Plasmodium falciparum S-adenosyl-L-homo-cysteine hydrolase were investigated. (c) 2008 Elsevier Ltd. All rights reserved.