(2-Chloro-9H-purin-6-yl)-phenethyl-amine | 204633-46-5

• 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: (2-Chloro-9H-purin-6-yl)-phenethyl-amine
• 英文别名: 2-chloro-N-(2-phenylethyl)-7H-purin-6-amine
• CAS: 204633-46-5
• 化学式: C₁₃H₁₂ClN₅
• mdl: MFCD09792061
• 分子量: 273.725
• InChiKey: SBBAPHCUEHMAKN-UHFFFAOYSA-N

物化性质

• 沸点：
  420.6±55.0 °C(Predicted)
• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.153
• 拓扑面积：
  66.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-溴甲基吡啶 、 (2-Chloro-9H-purin-6-yl)-phenethyl-amine 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-chloro-N-(2-phenylethyl)-9-(pyridin-3-ylmethyl)purin-6-amine
  参考文献：
  名称：

  Development of Potent Purine-Derived Nitrile Inhibitors of the Trypanosomal Protease TbcatB

  摘要：

  Human African trypanosomiasis (HAT), a major health concern in sub-Saharan Africa, is caused by the protozoan parasite Trypanosoma brucei. Recent studies have shown that a cathepsin B like protease, TbcatB, is essential to the survival of T brucei in vitro (Mackey, Z. B.; O'Brien, T. C.; Greenbaum, D. C.; Blank, R. B.; McKerrow, J. H. J. Biol. Chem. 2004, 279, 48426-48433). Herein, we describe the first inhibitors of TbcatB, a series of purine nitriles. The compounds are potent trypanocides, killing the parasite with a high degree of selectivity over a panel of three human cell lines. In addition, a predictive model of trypanocidal activity was developed on the basis of potency against TbcatB and various calculated physical property descriptors.

  DOI：

  10.1021/jm070760l
• 作为产物：
  描述：

  2-苯乙胺 、 2,6-二氯嘌呤 以 仲丁醇 为溶剂， 生成 (2-Chloro-9H-purin-6-yl)-phenethyl-amine
  参考文献：
  名称：

  Development of Potent Purine-Derived Nitrile Inhibitors of the Trypanosomal Protease TbcatB

  摘要：

  Human African trypanosomiasis (HAT), a major health concern in sub-Saharan Africa, is caused by the protozoan parasite Trypanosoma brucei. Recent studies have shown that a cathepsin B like protease, TbcatB, is essential to the survival of T brucei in vitro (Mackey, Z. B.; O'Brien, T. C.; Greenbaum, D. C.; Blank, R. B.; McKerrow, J. H. J. Biol. Chem. 2004, 279, 48426-48433). Herein, we describe the first inhibitors of TbcatB, a series of purine nitriles. The compounds are potent trypanocides, killing the parasite with a high degree of selectivity over a panel of three human cell lines. In addition, a predictive model of trypanocidal activity was developed on the basis of potency against TbcatB and various calculated physical property descriptors.

  DOI：

  10.1021/jm070760l

文献信息

• Solution-phase synthesis of 2,6,9-trisubstituted purines
  作者：Maria T. Fiorini、Chris Abell

  DOI：10.1016/s0040-4039(98)00098-7

  日期：1998.3

  A simple three-step method for the solution-phase combinatorial synthesis of 2,6,9-trisubstituted purines from 2,6-dichloropurine is described. The synthesis exploits the use of resin capture to remove excess reagent used in the final step. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Development of Potent Purine-Derived Nitrile Inhibitors of the Trypanosomal Protease TbcatB
  作者：Jeremy P. Mallari、Anang A. Shelat、Terri Obrien、Conor R. Caffrey、Aaron Kosinski、Michele Connelly、Michael Harbut、Doron Greenbaum、James H. McKerrow、R. Kiplin Guy

  DOI：10.1021/jm070760l

  日期：2008.2.1

  Human African trypanosomiasis (HAT), a major health concern in sub-Saharan Africa, is caused by the protozoan parasite Trypanosoma brucei. Recent studies have shown that a cathepsin B like protease, TbcatB, is essential to the survival of T brucei in vitro (Mackey, Z. B.; O'Brien, T. C.; Greenbaum, D. C.; Blank, R. B.; McKerrow, J. H. J. Biol. Chem. 2004, 279, 48426-48433). Herein, we describe the first inhibitors of TbcatB, a series of purine nitriles. The compounds are potent trypanocides, killing the parasite with a high degree of selectivity over a panel of three human cell lines. In addition, a predictive model of trypanocidal activity was developed on the basis of potency against TbcatB and various calculated physical property descriptors.