diethyl [2-(6-amino-9H-purin-9-yl)ethyl]phosphonate | 121149-94-8

• 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: diethyl [2-(6-amino-9H-purin-9-yl)ethyl]phosphonate
• 英文别名: 9-(2-Diethoxyphosphorylethyl)purin-6-amine
• CAS: 121149-94-8
• 化学式: C₁₁H₁₈N₅O₃P
• 分子量: 299.269
• InChiKey: KQGDOSXEWVSYQG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  105
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  diethyl [2-(6-amino-9H-purin-9-yl)ethyl]phosphonate 在 potassium tert-butylate 、 溴 、 sodium acetate 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.75h， 生成 {2-[6-amino-8-(7-chlorobenzothiazol-2-ylsulfanyl)-purin-9-yl]-ethyl}-phosphonic acid diethyl ester
  参考文献：
  名称：

  7‘-Substituted Benzothiazolothio- and Pyridinothiazolothio-Purines as Potent Heat Shock Protein 90 Inhibitors

  摘要：

  We report on the discovery of benzo- and pyridino-thiazolothiopurines as potent heat shock protein 90 inhibitors. The benzothiazole moiety is exceptionally sensitive to substitutions on the aromatic ring with a 7'-substituent essential for activity. Some of these compounds exhibit low nanomolar inhibition activity in a Her-2 degradation assay (28-150 nM), good aqueous solubility, and oral bioavailability profiles in mice. In vivo efficacy experiments demonstrate that compounds of this class inhibit tumor growth in an N87 human colon cancer xenograft model via oral administration as shown with compound 37 (8-(7-chlorobenzothiazol-2- ylsulfanyl)-9-(2-cyclopropylamino-ethyl)-9H-purin-6-ylamine).

  DOI：

  10.1021/jm051146h
• 作为产物：
  描述：

  腺嘌呤 、 alkaline earth salt of/the/ methylsulfuric acid 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以79%的产率得到diethyl [2-(6-amino-9H-purin-9-yl)ethyl]phosphonate
  参考文献：
  名称：

  7‘-Substituted Benzothiazolothio- and Pyridinothiazolothio-Purines as Potent Heat Shock Protein 90 Inhibitors

  摘要：

  We report on the discovery of benzo- and pyridino-thiazolothiopurines as potent heat shock protein 90 inhibitors. The benzothiazole moiety is exceptionally sensitive to substitutions on the aromatic ring with a 7'-substituent essential for activity. Some of these compounds exhibit low nanomolar inhibition activity in a Her-2 degradation assay (28-150 nM), good aqueous solubility, and oral bioavailability profiles in mice. In vivo efficacy experiments demonstrate that compounds of this class inhibit tumor growth in an N87 human colon cancer xenograft model via oral administration as shown with compound 37 (8-(7-chlorobenzothiazol-2- ylsulfanyl)-9-(2-cyclopropylamino-ethyl)-9H-purin-6-ylamine).

  DOI：

  10.1021/jm051146h

文献信息

• Synthesis of Adenines with a Phosphorus-Containing Group in the 9-Position
  作者：A. V. Smolobochkin、A. S. Gazizov、L. I. Vagapova、Yu. K. Voronina、A. R. Burilov、A. A. Bogdanov、M. A. Pudovik

  DOI：10.1134/s1070428018060180

  日期：2018.6

  Adenine derivatives with a phosphorus-containing substituent on N-9 have been synthesized, and their structure has been confirmed by H-1, C-13, and P-31 NMR and IR spectroscopy, X-ray diffraction, MALDI mass spectrometry, and elemental analysis.
• HOLY, ANTONIN;ROSENBERG, IVAN;DVORAKOVA, HANA;DECLERCQ, ERIK, NUCLEOSIDES AND NUCLEOTIDES, 7,(1988) N-6, C. 667-670
  作者：HOLY, ANTONIN、ROSENBERG, IVAN、DVORAKOVA, HANA、DECLERCQ, ERIK

  DOI：——

  日期：——
• 7‘-Substituted Benzothiazolothio- and Pyridinothiazolothio-Purines as Potent Heat Shock Protein 90 Inhibitors
  作者：Lin Zhang、Junhua Fan、Khang Vu、Kevin Hong、Jean-Yves Le Brazidec、Jiandong Shi、Marco Biamonte、David J. Busch、Rachel E. Lough、Roy Grecko、Yingqing Ran、John L. Sensintaffar、Adeela Kamal、Karen Lundgren、Francis J. Burrows、Robert Mansfield、Gregg A. Timony、Edgar H. Ulm、Srinivas R. Kasibhatla、Marcus F. Boehm

  DOI：10.1021/jm051146h

  日期：2006.8.1

  We report on the discovery of benzo- and pyridino-thiazolothiopurines as potent heat shock protein 90 inhibitors. The benzothiazole moiety is exceptionally sensitive to substitutions on the aromatic ring with a 7'-substituent essential for activity. Some of these compounds exhibit low nanomolar inhibition activity in a Her-2 degradation assay (28-150 nM), good aqueous solubility, and oral bioavailability profiles in mice. In vivo efficacy experiments demonstrate that compounds of this class inhibit tumor growth in an N87 human colon cancer xenograft model via oral administration as shown with compound 37 (8-(7-chlorobenzothiazol-2- ylsulfanyl)-9-(2-cyclopropylamino-ethyl)-9H-purin-6-ylamine).