[2-(2,4,6-Trichloro-phenylamino)-4-trifluoromethyl-thiazol-5-yl]-methanol | 405878-87-7

• 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-(2,4,6-Trichloro-phenylamino)-4-trifluoromethyl-thiazol-5-yl]-methanol
• 英文别名: [2-(2,4,6-Trichloroanilino)-4-(trifluoromethyl)-1,3-thiazol-5-yl]methanol
• CAS: 405878-87-7
• 化学式: C₁₁H₆Cl₃F₃N₂OS
• 分子量: 377.602
• InChiKey: SXKHIKLCWZPHBC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  73.4
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [2-(2,4,6-Trichloro-phenylamino)-4-trifluoromethyl-thiazol-5-yl]-methanol 在 氯化亚砜 作用下， 反应 0.08h， 以91%的产率得到(5-chloromethyl-4-trifluoromethylthiazol-2-yl)-(2,4,6-trichlorophenyl)amine
  参考文献：
  名称：

  Optimization of CRF1R binding affinity of 2-(2,4,6-trichlorophenyl)-4-trifluoromethyl-5-aminomethylthiazoles through rapid and selective parallel synthesis

  摘要：

  An efficient approach was developed to synthesize 2-(2,4,6-trichlorophenylamino)-4-trifluoromethyl-5-aminomethylthiazoles, corticotropin-releasing factor type 1 receptor (CRF1R) antagonists, by monoalkylation of amines with chloromethyl intermediate 5. The effect of variations in aminomethyl side chain of 6 on binding affinity is discussed. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.10.055
• 作为产物：
  描述：

  2-(2,4,6-Trichloro-phenylamino)-4-trifluoromethyl-thiazole-5-carboxylic acid ethyl ester 在 二异丁基氢化铝 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以100%的产率得到[2-(2,4,6-Trichloro-phenylamino)-4-trifluoromethyl-thiazol-5-yl]-methanol
  参考文献：
  名称：

  Optimization of CRF1R binding affinity of 2-(2,4,6-trichlorophenyl)-4-trifluoromethyl-5-aminomethylthiazoles through rapid and selective parallel synthesis

  摘要：

  An efficient approach was developed to synthesize 2-(2,4,6-trichlorophenylamino)-4-trifluoromethyl-5-aminomethylthiazoles, corticotropin-releasing factor type 1 receptor (CRF1R) antagonists, by monoalkylation of amines with chloromethyl intermediate 5. The effect of variations in aminomethyl side chain of 6 on binding affinity is discussed. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.10.055

文献信息

• Substituted azole derivatives as inhibitors of corticotropin releasing factor
  申请人：——

  公开号：US20020161019A1

  公开（公告）日：2002-10-31

  The present invention relates to thiazoles, oxazoles, imidazoles and pharmaceutical compositions comprising said compounds antagonizing the corticotropin releasing factor receptor (“CRF receptor”) and 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.

  本发明涉及噻唑、噁唑、咪唑及含有这些化合物的药物组合物，其拮抗促肾上腺皮质激素释放因子受体（“CRF受体”），并可用于治疗抑郁症、焦虑症、情感障碍、饮食障碍、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和其他可以通过拮抗CRF-1受体来治疗的疾病。
• US6515005B2
  申请人：——

  公开号：US6515005B2

  公开（公告）日：2003-02-04
• Optimization of CRF1R binding affinity of 2-(2,4,6-trichlorophenyl)-4-trifluoromethyl-5-aminomethylthiazoles through rapid and selective parallel synthesis
  作者：Dmitry Zuev、Jodi A. Michne、Sokhom S. Pin、Jie Zhang、Matthew T. Taber、Gene M. Dubowchik

  DOI：10.1016/j.bmcl.2004.10.055

  日期：2005.1

  An efficient approach was developed to synthesize 2-(2,4,6-trichlorophenylamino)-4-trifluoromethyl-5-aminomethylthiazoles, corticotropin-releasing factor type 1 receptor (CRF1R) antagonists, by monoalkylation of amines with chloromethyl intermediate 5. The effect of variations in aminomethyl side chain of 6 on binding affinity is discussed. (C) 2004 Elsevier Ltd. All rights reserved.