1-(5,6-dichloro-1H-benzimidazol-2-yl)-2,2,2-trifluoroethane-1,1-diol | 929080-05-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 1-(5,6-dichloro-1H-benzimidazol-2-yl)-2,2,2-trifluoroethane-1,1-diol
• CAS: 929080-05-7
• 化学式: C₉H₅Cl₂F₃N₂O₂
• 分子量: 301.052
• InChiKey: IAIGLOJAJUEYBG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  69.1
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(5,6-dichloro-1H-benzimidazol-2-yl)-2,2,2-trifluoroethane-1,1-diol 反应 96.0h， 生成 1-(5,6-dichloro-1H-benzoimidazol-2-yl)-2,2,2-trifluoro-ethanone
  参考文献：
  名称：

  Synthesis of potent and tissue-selective androgen receptor modulators (SARMs): 2-(2,2,2)-Trifluoroethyl-benzimidazole scaffold

  摘要：

  The synthesis and in vivo SAR of 2-(2,2,2)-trifluoroethyl-benzimidazoles are described. Prostate antagonism and/or levator am agonism can be modulated by varying the substitution at the 2-position of 5,6-dichloro-benzimidazoles. Potent androgen agonists on the muscle were discovered that strongly bind to the androgen receptor (2-17 nM) and show potent in vivo efficacy (0.03-0.11 mg/day). True SARMs showing both prostate antagonism and levator am agonism were revealed. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.12.045
• 作为产物：
  描述：

  1-(5,6-dichloro-1H-benzoimidazol-2-yl)-2,2,2-trifluoro-ethanol 在 2,2,6,6-tetramethyl-piperidine-N-oxyl 作用下， 生成 1-(5,6-dichloro-1H-benzimidazol-2-yl)-2,2,2-trifluoroethane-1,1-diol
  参考文献：
  名称：

  Synthesis and SAR of potent and selective androgen receptor antagonists: 5,6-Dichloro-benzimidazole derivatives

  摘要：

  The synthesis and in vivo SAR of 5,6-dichloro-benzimidazole derivatives as novel selective androgen receptor antagonists are described. During screening of 2-alkyl benzimidazoles, it was found that a trifluoromethyl group greatly enhances antagonist activity in the prostate. Benzimidazole I is a potent AR antagonist in the rat prostate (ID50 = 0.15 mg/day). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.10.071

文献信息

• 含氟手性胺类化合物的合成方法
  申请人：凯莱英医药集团(天津)股份有限公司

  公开号：CN110950788B

  公开（公告）日：2020-06-16

  本发明提供了一种含氟手性胺类化合物的合成方法。该合成方法包括：氨基供体与含氟二羟基缩酮类化合物在转氨酶的催化下，反应生成含氟手性胺类化合物；其中，转氨酶来源于多个菌种。本申请的转氨酶对含氟二羟基缩酮类化合物具有底物特异性，能够有效催化此类底物转化为含氟手性胺类化合物，而且，该转氨酶对多种含氟二羟基缩酮类化合物都具有催化活性，反应选择性和活性均较高。该生物酶催化合成方法不仅路线短，产品收率高，而且大大降低了生产成本，减少了有机溶剂和三废产生。
• 2-(2,2,2-Trifluoroethyl)-5,6-dichlorobenzimidazole derivatives as potent androgen receptor antagonists
  作者：Raymond A. Ng、Jihua Guan、Vernon C. Alford、James C. Lanter、George F. Allan、Tifanie Sbriscia、Scott G. Lundeen、Zhihua Sui

  DOI：10.1016/j.bmcl.2006.11.047

  日期：2007.2

  The synthesis and in vivo SAR of N-benzyl, N-aceto, and N-ethylene ether derivatives of 2-(2,2,2-trifluoroethyl)-5,6dichloro-benzimidazole as novel androgen receptor antagonists are described. SAR studies led to the discovery of 4-bromo-benzyl benzimidazole 17 as a more potent androgen receptor antagonist in the rat prostate (ID50 = 0.13 mg/day), compared with bicalutamide (ID50 = 0.23 mg/day). (c) 2006 Elsevier Ltd. All rights reserved.
• Synthesis and SAR of potent and selective androgen receptor antagonists: 5,6-Dichloro-benzimidazole derivatives
  作者：Raymond A. Ng、Jihua Guan、Vernon C. Alford、James C. Lanter、George F. Allan、Tifanie Sbriscia、Olivia Linton、Scott G. Lundeen、Zhihua Sui

  DOI：10.1016/j.bmcl.2006.10.071

  日期：2007.2

  The synthesis and in vivo SAR of 5,6-dichloro-benzimidazole derivatives as novel selective androgen receptor antagonists are described. During screening of 2-alkyl benzimidazoles, it was found that a trifluoromethyl group greatly enhances antagonist activity in the prostate. Benzimidazole I is a potent AR antagonist in the rat prostate (ID50 = 0.15 mg/day). (c) 2006 Elsevier Ltd. All rights reserved.
• Synthesis of potent and tissue-selective androgen receptor modulators (SARMs): 2-(2,2,2)-Trifluoroethyl-benzimidazole scaffold
  作者：Raymond A. Ng、James C. Lanter、Vernon C. Alford、George F. Allan、Tifanie Sbriscia、Scott G. Lundeen、Zhihua Sui

  DOI：10.1016/j.bmcl.2006.12.045

  日期：2007.3

  The synthesis and in vivo SAR of 2-(2,2,2)-trifluoroethyl-benzimidazoles are described. Prostate antagonism and/or levator am agonism can be modulated by varying the substitution at the 2-position of 5,6-dichloro-benzimidazoles. Potent androgen agonists on the muscle were discovered that strongly bind to the androgen receptor (2-17 nM) and show potent in vivo efficacy (0.03-0.11 mg/day). True SARMs showing both prostate antagonism and levator am agonism were revealed. (c) 2006 Elsevier Ltd. All rights reserved.