2-Bromo-5-trifluoromethyl-3-[3-(2,4,6-trimethyl-phenylamino)-propyl]-3H-imidazole-4-carboxylic acid ethyl ester | 444325-69-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-Bromo-5-trifluoromethyl-3-[3-(2,4,6-trimethyl-phenylamino)-propyl]-3H-imidazole-4-carboxylic acid ethyl ester
• 英文别名: Ethyl 2-bromo-5-(trifluoromethyl)-3-[3-(2,4,6-trimethylanilino)propyl]imidazole-4-carboxylate
• CAS: 444325-69-3
• 化学式: C₁₉H₂₃BrF₃N₃O₂
• 分子量: 462.31
• InChiKey: HTCCQEPSMDWSAQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  56.2
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-Bromo-5-trifluoromethyl-3-[3-(2,4,6-trimethyl-phenylamino)-propyl]-3H-imidazole-4-carboxylic acid ethyl ester 在 Ag(I) salt 作用下， 以 环丁砜 为溶剂， 生成 ethyl 2-(trifluoromethyl)-8-(2,4,6-trimethylphenyl)-6,7-dihydro-5H-imidazo[1,2-a]pyrimidine-3-carboxylate
  参考文献：
  名称：

  Design, synthesis and evaluation of constrained tetrahydroimidazopyrimidine derivatives as antagonists of corticotropin-releasing factor type 1 receptor (CRF1R)

  摘要：

  Several tetrahydroimidazopyrimidines were prepared using silver assisted cyclization as the key step. The binding affinities of compounds thus prepared were evaluated in vitro toward hCRF(1)R. Initial lead compound 16 (K-i = 32 nM) demonstrated modest putative anxiolytic effects in the mouse canopy test. Further optimization using parallel synthesis provided compounds with K-i's <50 nM. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.01.127
• 作为产物：
  描述：

  (3-Bromo-propyl)-(2,4,6-trimethyl-phenyl)-amine 、 ethyl 2-bromo-4-(trifluoromethyl)-1H-imidazole-5-carboxylate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-Bromo-5-trifluoromethyl-3-[3-(2,4,6-trimethyl-phenylamino)-propyl]-3H-imidazole-4-carboxylic acid ethyl ester
  参考文献：
  名称：

  Design, synthesis and evaluation of constrained tetrahydroimidazopyrimidine derivatives as antagonists of corticotropin-releasing factor type 1 receptor (CRF1R)

  摘要：

  Several tetrahydroimidazopyrimidines were prepared using silver assisted cyclization as the key step. The binding affinities of compounds thus prepared were evaluated in vitro toward hCRF(1)R. Initial lead compound 16 (K-i = 32 nM) demonstrated modest putative anxiolytic effects in the mouse canopy test. Further optimization using parallel synthesis provided compounds with K-i's <50 nM. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.01.127

文献信息

• Imidazolyl derivatives as corticotropin releasing factor inhibitors
  申请人：——

  公开号：US20020183375A1

  公开（公告）日：2002-12-05

  The present invention relates to novel heterocyclic antagonists of Formula (I) and pharmaceutical compositions comprising said antagonists of the corticotropin releasing factor receptor (“CRF receptor”) 1 useful for the treatment of depression, anxiety, affective disorders, feeding disorders, post-traumatic stress disorder, headache, drug addiction, inflammatory disorders, drug or alcohol withdrawal symptoms and other conditions the treatment of which can be effected by the antagonism of the CRF-1 receptor.

  本发明涉及一种新型杂环拮抗剂，其化学式为(I)，以及包含所述拮抗剂的药物组合物，用于治疗抑郁症、焦虑症、情感障碍、进食障碍、创伤后应激障碍、头痛、药物成瘾、炎症性疾病、药物或酒精戒断症状以及其他可以通过拮抗CRF-1受体来治疗的病症。
• US6888004B2
  申请人：——

  公开号：US6888004B2

  公开（公告）日：2005-05-03
• US7125990B2
  申请人：——

  公开号：US7125990B2

  公开（公告）日：2006-10-24
• US7211669B2
  申请人：——

  公开号：US7211669B2

  公开（公告）日：2007-05-01
• US7238699B2
  申请人：——

  公开号：US7238699B2

  公开（公告）日：2007-07-03