(3R,4R)-4-(adenin-9-yl)-3-hydroxypyrrolidin-1-ylcarbonylphosphonic acid | 1219028-41-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (3R,4R)-4-(adenin-9-yl)-3-hydroxypyrrolidin-1-ylcarbonylphosphonic acid
• 英文别名: (3R,4R)-4-(thymin-1-yl)-3-hydroxypyrrolidin-N-ylcarbonylphosphonic acid；[(3R,4R)-3-hydroxy-4-(5-methyl-2,4-dioxopyrimidin-1-yl)pyrrolidine-1-carbonyl]phosphonic acid
• CAS: 1219028-41-7
• 化学式: C₁₀H₁₄N₃O₇P
• 分子量: 319.211
• InChiKey: CFDPBOPUGKGHEZ-RNFRBKRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.2
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  148
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  在 三甲基溴硅烷 作用下， 以 乙腈 为溶剂， 生成 (3R,4R)-4-(adenin-9-yl)-3-hydroxypyrrolidin-1-ylcarbonylphosphonic acid
  参考文献：
  名称：

  Pyrrolidine nucleotide analogs with a tunable conformation

  摘要：

  核苷酸类似物中吡咯烷环的构象偏好通过核磁共振和分子建模进行了研究。研究了羟基和核碱基取代基的相对构型以及吡咯烷氮原子的烷基化或酰化对吡咯烷环构象的影响。构象分析结果表明，烷基化/酰化可以有效地用于调节整个伪旋转周期中吡咯烷环的构象。

  DOI：

  10.3762/bjoc.10.205

文献信息

• Structural diversity of nucleoside phosphonic acids as a key factor in the discovery of potent inhibitors of rat T-cell lymphoma thymidine phosphorylase
  作者：Petr Kočalka、Dominik Rejman、Václav Vaněk、Markéta Rinnová、Ivana Tomečková、Šárka Králíková、Magdalena Petrová、Ondřej Páv、Radek Pohl、Miloš Buděšínský、Radek Liboska、Zdeněk Točík、Natalya Panova、Ivan Votruba、Ivan Rosenberg

  DOI：10.1016/j.bmcl.2009.12.081

  日期：2010.2

  Structurally diverse, sugar-modified, thymine-containing nucleoside phosphonic acids were evaluated for their ability to inhibit thymidine phosphorylase (TP, EC 2.4.2.4) purified from spontaneous T-cell lymphomas of an inbred Sprague-Dawley rat strain. From a large set of tested compounds, among them a number of pyrrolidine-based derivatives, 10 nucleotide analogues with IC50 values below 1 mu M were selected. Out of them, four compounds strongly inhibited the enzyme with IC50 values lying in a range of 11-45 nM. These most potent compounds might be bi-substrate analogues. (C) 2009 Elsevier Ltd. All rights reserved.
• Pyrrolidine nucleotide analogs with a tunable conformation
  作者：Lenka Poštová Slavětínská、Dominik Rejman、Radek Pohl

  DOI：10.3762/bjoc.10.205

  日期：——

  Conformational preferences of the pyrrolidine ring in nucleotide analogs 7–14 were investigated by means of NMR and molecular modeling. The effect of the relative configuration of hydroxy and nucleobase substituents as well as the effect of the alkylation or acylation of the pyrrolidine nitrogen atom on the conformation of the pyrrolidine ring were studied. The results of a conformational analysis show that the alkylation/acylation can be effectively used for tuning the pyrrolidine conformation over the whole pseudorotation cycle.

  核苷酸类似物中吡咯烷环的构象偏好通过核磁共振和分子建模进行了研究。研究了羟基和核碱基取代基的相对构型以及吡咯烷氮原子的烷基化或酰化对吡咯烷环构象的影响。构象分析结果表明，烷基化/酰化可以有效地用于调节整个伪旋转周期中吡咯烷环的构象。