[(2R,5S)-5-(2-Amino-6-chloro-purin-9-ylmethyl)-tetrahydro-furan-2-yl]-phosphonic acid diisopropyl ester | 497178-97-9

• 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: [(2R,5S)-5-(2-Amino-6-chloro-purin-9-ylmethyl)-tetrahydro-furan-2-yl]-phosphonic acid diisopropyl ester
• 英文别名: 6-chloro-9-[[(2S,5R)-5-[oxido-di(propan-2-yloxy)phosphaniumyl]oxolan-2-yl]methyl]purin-2-amine
• CAS: 497178-97-9
• 化学式: C₁₆H₂₅ClN₅O₄P
• 分子量: 417.832
• InChiKey: SINBVDUGKOVZFG-NWDGAFQWSA-N

物化性质

• 沸点：
  615.0±65.0 °C(Predicted)
• 密度：
  1.55±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  120
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  [(2R,5S)-5-(2-Amino-6-chloro-purin-9-ylmethyl)-tetrahydro-furan-2-yl]-phosphonic acid diisopropyl ester 反应 16.0h， 生成
  参考文献：
  名称：

  Novel nucleotide phosphonate analogues with potent antitumor activity

  摘要：

  We have identified several nucleotide phosphonates demonstrating in vitro antiproliferative activity in several human cancer cell lines with IC50 values in the muM range. The synthesis as well as structure-activity relationship are described. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00679-0
• 作为产物：
  描述：

  2-氨基-6-氯嘌呤 、 (2R,5S)-2-di(propan-2-yloxy)phosphoryl-5-(iodomethyl)oxolane 在 CsCO₃ 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以50%的产率得到[(2R,5S)-5-(2-Amino-6-chloro-purin-9-ylmethyl)-tetrahydro-furan-2-yl]-phosphonic acid diisopropyl ester
  参考文献：
  名称：

  A stereoselective route to bioactive nucleotide phosphonate analogs

  摘要：

  Recently we have reported a novel class of tetrahydrofuran phosplionates of which trans guanine nucleotide analog la showed potent antiviral activity as well as antitumor activity. In this paper we describe a stereoselective route where the key step involves an iodoetherification of a alpha-hydroxyphosphonate to generate the trans tetrahydrofuran with high stereoselectivity. The same intermediate 2 was also used to access the key intermediate for the cis analog 1b. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.09.071

文献信息

• Novel nucleotide phosphonate analogues with potent antitumor activity
  作者：Monica Bubenik、Rabindra Rej、Nghe Nguyen-Ba、Giorgio Attardo、France Ouellet、Laval Chan

  DOI：10.1016/s0960-894x(02)00679-0

  日期：2002.11

  We have identified several nucleotide phosphonates demonstrating in vitro antiproliferative activity in several human cancer cell lines with IC50 values in the muM range. The synthesis as well as structure-activity relationship are described. (C) 2002 Elsevier Science Ltd. All rights reserved.
• A stereoselective route to bioactive nucleotide phosphonate analogs
  作者：Monica Bubenik、Patrice Préville、Josée Dugas、Giorgio Attardo、Laval Chan

  DOI：10.1016/j.tetlet.2003.09.071

  日期：2003.11

  Recently we have reported a novel class of tetrahydrofuran phosplionates of which trans guanine nucleotide analog la showed potent antiviral activity as well as antitumor activity. In this paper we describe a stereoselective route where the key step involves an iodoetherification of a alpha-hydroxyphosphonate to generate the trans tetrahydrofuran with high stereoselectivity. The same intermediate 2 was also used to access the key intermediate for the cis analog 1b. (C) 2003 Elsevier Ltd. All rights reserved.