methanesulfonic acid 3-[6-amino-8-(7-chlorobenzothiazol-2-ylsulfanyl)-purin-9-yl]-propyl ester | 908355-86-2

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: methanesulfonic acid 3-[6-amino-8-(7-chlorobenzothiazol-2-ylsulfanyl)-purin-9-yl]-propyl ester
• 英文别名: 3-[6-Amino-8-[(7-chloro-1,3-benzothiazol-2-yl)sulfanyl]purin-9-yl]propyl methanesulfonate
• CAS: 908355-86-2
• 化学式: C₁₆H₁₅ClN₆O₃S₃
• 分子量: 470.985
• InChiKey: SFKPTZZADPKOFX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  188
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  methanesulfonic acid 3-[6-amino-8-(7-chlorobenzothiazol-2-ylsulfanyl)-purin-9-yl]-propyl ester 、 叔丁胺 以45%的产率得到9-(3-tert-butylamino-propyl)-8-(7-chlorobenzothiazol-2-ylsulfanyl)-9H-purin-6-ylamine
  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：

  7-氯-2(3H)-苯并噻唑硫酮 在 potassium tert-butylate 、 氨 、 三乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.42h， 生成 methanesulfonic acid 3-[6-amino-8-(7-chlorobenzothiazol-2-ylsulfanyl)-purin-9-yl]-propyl 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

文献信息

• 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).