4-benzoyloxymethyl-7-(2,3-O-isopropylidene-5-O-tert-butyldimethylsilyl-β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine | 1172127-89-7

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 吡咯并嘧啶核苷和核苷酸
• 英文名称: 4-benzoyloxymethyl-7-(2,3-O-isopropylidene-5-O-tert-butyldimethylsilyl-β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine
• 英文别名: [7-[(3aR,4R,6R,6aR)-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]pyrrolo[2,3-d]pyrimidin-4-yl]methyl benzoate
• CAS: 1172127-89-7
• 化学式: C₂₈H₃₇N₃O₆Si
• 分子量: 539.704
• InChiKey: HXDHZOBNRWYVKQ-VWBWNGLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.23
• 重原子数：
  38
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  93.9
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4-benzoyloxymethyl-7-(2,3-O-isopropylidene-5-O-tert-butyldimethylsilyl-β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 4-hydroxymethyl-7-(2,3-O-isopropylidene-5-O-tert-butyldimethylsilyl-β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine
  参考文献：
  名称：

  6-(Het)aryl-7-Deazapurine Ribonucleosides as Novel Potent Cytostatic Agents

  摘要：

  A series of novel 7-deazapurine ribonucleosides bearing an alkyl, aryl, or lietaryl group in position 6 and H, F, or Cl atom in position 7 has been prepared either by Pd-catalyzed cross-coupling reactions of the corresponding protected 6-clilot-o-(7-h ilogeiiztted-)7-deiz ipurine ribonucleosides with alkyl- or (het)arylorganometallics followed by deprotection, or by single-step aqueous phase cross-coupling reactions of unprotected 6-chloro-(7-lialogen tted-)7-de iz tl)tii-iiie ri bon ucleos ides with (het)arylboronic acids. Significant cytostatic effect was detected With a Substantial proportion ofthe prepared compounds. The most potent were 7-H or 7-17 derivatives of 6-furyl- or 6-thienyl-7-deazapurines displaying cytostatic activity in multiple cancer cell lines with a geometric mean of 50% growth inhibition concentration ranging from 16 to 96 nM, a potency comparable to or better than that of the nucleoside analogue clofarabinc. lntr icel]Lll ll'pliosphoi-yl itioil to niono- and triphosphates and the inhibition of total RNA synthesis was denionstrated in preliminary study of metabolism and tinechanistin of action Studies.

  DOI：

  10.1021/jm901428k
• 作为产物：
  描述：

  [(benzoyloxy)methyl]zinc iodide 、 4-chloro-7-(5'-O-tert-butyldimethylsilyl-2',3'-O-isopropylidene-β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine 在 四(三苯基膦)钯 作用下， 以 四氢呋喃 为溶剂， 反应 15.0h， 以54%的产率得到4-benzoyloxymethyl-7-(2,3-O-isopropylidene-5-O-tert-butyldimethylsilyl-β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine
  参考文献：
  名称：

  [EN] NOVEL CYTOSTATIC 7-DEAZAPURINE NUCLEOSIDES
  [FR] NOUVEAUX NUCLÉOSIDES 7-DÉAZAPURINE CYTOSTATIQUES

  摘要：

  这项发明提供了式（I）的化合物，其中R1和R2具有规范中定义的任何值及其盐，以及包含这些化合物的组合物和利用这些化合物的治疗方法。

  公开号：

  WO2009089804A1

文献信息

• [EN] NOVEL CYTOSTATIC 7-DEAZAPURINE NUCLEOSIDES<br/>[FR] NOUVEAUX NUCLÉOSIDES 7-DÉAZAPURINE CYTOSTATIQUES
  申请人：ACAD OF SCIENCE CZECH REPUBLIC

  公开号：WO2009089804A1

  公开（公告）日：2009-07-23

  The invention provides compounds of formula (I), wherein R1 and R2 have any of the values defined in the specification and salts thereof, as well as compositions comprising such compounds and therapeutic methods that utilize such compounds.

  这项发明提供了式（I）的化合物，其中R1和R2具有规范中定义的任何值及其盐，以及包含这些化合物的组合物和利用这些化合物的治疗方法。
• 6-(Het)aryl-7-Deazapurine Ribonucleosides as Novel Potent Cytostatic Agents
  作者：Petr Nauš、Radek Pohl、Ivan Votruba、Petr Džubák、Marián Hajdúch、Ria Ameral、Gabriel Birkuš、Ting Wang、Adrian S. Ray、Richard Mackman、Tomas Cihlar、Michal Hocek

  DOI：10.1021/jm901428k

  日期：2010.1.14

  A series of novel 7-deazapurine ribonucleosides bearing an alkyl, aryl, or lietaryl group in position 6 and H, F, or Cl atom in position 7 has been prepared either by Pd-catalyzed cross-coupling reactions of the corresponding protected 6-clilot-o-(7-h ilogeiiztted-)7-deiz ipurine ribonucleosides with alkyl- or (het)arylorganometallics followed by deprotection, or by single-step aqueous phase cross-coupling reactions of unprotected 6-chloro-(7-lialogen tted-)7-de iz tl)tii-iiie ri bon ucleos ides with (het)arylboronic acids. Significant cytostatic effect was detected With a Substantial proportion ofthe prepared compounds. The most potent were 7-H or 7-17 derivatives of 6-furyl- or 6-thienyl-7-deazapurines displaying cytostatic activity in multiple cancer cell lines with a geometric mean of 50% growth inhibition concentration ranging from 16 to 96 nM, a potency comparable to or better than that of the nucleoside analogue clofarabinc. lntr icel]Lll ll'pliosphoi-yl itioil to niono- and triphosphates and the inhibition of total RNA synthesis was denionstrated in preliminary study of metabolism and tinechanistin of action Studies.