(2,6-Dichloro-4-trifluoromethyl-phenyl)-thiourea | 133307-10-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2,6-Dichloro-4-trifluoromethyl-phenyl)-thiourea
• 英文别名: [2,6-Dichloro-4-(trifluoromethyl)phenyl]thiourea
• CAS: 133307-10-5
• 化学式: C₈H₅Cl₂F₃N₂S
• 分子量: 289.108
• InChiKey: NIAMKDVGKMOWBT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  70.1
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2,6-Dichloro-4-trifluoromethyl-phenyl)-thiourea 在 三甲基铝 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 30.0h， 生成 2-(2,6-Dichloro-4-trifluoromethyl-phenylamino)-4-trifluoromethyl-thiazole-5-carboxylic acid cyclopropylmethyl-propyl-amide
  参考文献：
  名称：

  2-Arylaminothiazoles as high-affinity corticotropin-Releasing factor 1 receptor (CRF1R) antagonists: synthesis, binding studies and behavioral efficacy

  摘要：

  2-Arylamino-4-trifluoromethyl-5-aminomethylthiazoles represent a novel series of high-affinity corticotropin releasing factor-1 receptor (CRF1R) antagonists that are prepared in three steps in good overall yields. Herein, we report binding SAR as well as anxiolytic activity of an exemplary compound (7a, K-i = 8.6 nM) in a mouse canopy model. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.08.055

文献信息

• Pyrimidinone derivatives
  申请人：ZENECA LIMITED

  公开号：EP0396250A1

  公开（公告）日：1990-11-07

  A compound of formula (I) : wherein R¹ and R² are independently selected from hydrogen, halogen, haloalkyl, alkoxy or nitro, provided that R¹ and R² are not both nitro; R³ and R⁴ are independently selected from hydrogen, halogen, alkyl or cycloalkyl; R⁵ is halogen, nitro, haloalkyl, haloalkoxy or -S(O)nR¹⁰; R⁶ is halogen, nitro, haloalkyl, haloalkoxy or -S(O)nR¹⁰; R⁷ is hydrogen, halogen, hydroxyalkyl, cyano, nitro, alkoxy, -S(O)nR¹⁰, NR¹¹R¹², haloalkyl or formyl; R⁸ is hydrogen, halogen, NR¹¹R¹², alkyl, cycloalkyl or S(O)n R¹⁰; and R⁹ is oxygen or sulphur; where n is 0, 1 or 2; and R¹⁰ is alkyl, haloalkyl or cycloalkyl; and R¹¹ and R¹² are independently selected from hydrogen, alkyl or cycloalkyl or R¹¹ and R¹² together with the nitrogen to which they are attached form a heterocylic group; provided that when R⁵ is trifluoromethyl at least one of the following applies: (i) R¹ or R² is haloalkyl or alkoxy; (ii) R³ or R⁴ are alkyl or cycloalkyl; (iii) R⁶ is haloalkoxy, nitro or -S(O)nR¹⁰; (iv) R⁷ is nitro, hydroxyalkyl, alkoxy, S(O)nR¹⁰, NR¹¹R¹², formyl or haloalkyl; (v) R⁸ is other than hydrogen; (vi) R⁹ is sulphur; and further provided that (a) R¹, R², R³ and R⁴ are not all fluorine and (b) when R⁵ is chlorine, R¹ and R² are both halogen.

  一种式 (I) 的化合物： 其中 R¹ 和 R² 独立选自氢、卤素、卤代烷基、烷氧基或硝基，条件是 R¹ 和 R² 不同时为硝基；R³ 和 R⁴ 独立选自氢、卤素、烷基或环烷基；R⁵ 是卤素、硝基、卤代烷基、卤代烷氧基或 -S(O)nR¹⁰； R⁶ 是卤素、硝基、卤代烷基、卤代烷氧基或 -S(O)nR¹⁰； R⁷ 是氢、卤素、羟烷基、氰基、硝基、烷氧基、-S(O)nR¹⁰、NR¹R¹²、卤代烷基或甲酰基；R⁸ 是氢、卤素、NR¹¹R¹²、烷基、环烷基或 S(O)nR¹⁰ ；R⁹ 是氧或硫；其中 n 是 0、1 或 2；R¹⁰ 是烷基、卤代烷基或环烷基；和 R¹¹ 和 R¹² 独立地选自氢、烷基或环烷基，或 R¹¹ 和 R¹² 与它们所连接的氮一起形成杂环基团；但当 R⁵ 是三氟甲基时，以下至少一种情况适用： (i) R¹ 或 R² 是卤代烷基或烷氧基； (ii) R³ 或 R⁴ 是烷基或环烷基； (iii) R⁶ 是卤代烷氧基、硝基或-S(O)nR¹⁰； (iv) R⁷ 是硝基、羟烷基、烷氧基、S(O)nR¹⁰、NR¹R¹²、甲酰基或卤代烷基； (v) R⁸ 不是氢； (vi) R⁹是硫；以及 (a) R¹、R²、R³ 和 R⁴ 并非都是氟，以及 (b) 当 R⁵ 是氯时，R¹ 和 R² 都是卤素。
• US5104878A
  申请人：——

  公开号：US5104878A

  公开（公告）日：1992-04-14
• 2-Arylaminothiazoles as high-affinity corticotropin-Releasing factor 1 receptor (CRF1R) antagonists: synthesis, binding studies and behavioral efficacy
  作者：Gene M. Dubowchik、Jodi A. Michne、Dmitry Zuev、Wendy Schwartz、Paul M. Scola、Clint A. James、Edward H. Ruediger、Sokhom S. Pin、Kevin D. Burris、Lynn A. Balanda、Qi Gao、Dedong Wu、Lawrence Fung、Tracey Fiedler、Kaitlin E. Browman、Matthew T. Taber、Jie Zhang

  DOI：10.1016/j.bmcl.2003.08.055

  日期：2003.11

  2-Arylamino-4-trifluoromethyl-5-aminomethylthiazoles represent a novel series of high-affinity corticotropin releasing factor-1 receptor (CRF1R) antagonists that are prepared in three steps in good overall yields. Herein, we report binding SAR as well as anxiolytic activity of an exemplary compound (7a, K-i = 8.6 nM) in a mouse canopy model. (C) 2003 Elsevier Ltd. All rights reserved.