(S)-8-{5-[3-methyl-4-(trifluoromethyl)phenyl]oxazol-2-ylamino}-1,2,3,4-tetrahydronaphthalen-2-ol | 1146695-31-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (S)-8-{5-[3-methyl-4-(trifluoromethyl)phenyl]oxazol-2-ylamino}-1,2,3,4-tetrahydronaphthalen-2-ol
• 英文别名: (2S)-8-({4-methyl-5-[4-(trifluoromethyl)phenyl]-1,3-oxazol-2-yl}amino)-1,2,3,4-tetrahydronaphthalen-2-ol；(2S)-8-[[4-methyl-5-[4-(trifluoromethyl)phenyl]-1,3-oxazol-2-yl]amino]-1,2,3,4-tetrahydronaphthalen-2-ol
• CAS: 1146695-31-9
• 化学式: C₂₁H₁₉F₃N₂O₂
• 分子量: 388.389
• InChiKey: CHLCWXNTFXVPAL-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  58.3
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (S)-8-amino-1,2,3,4-tetrahydronaphthalen-2-ol 、 2-chloro-4-methyl-5-[4-(trifluoromethyl)phenyl]oxazole 在 碳酸氢钠 、 sodium chloride 作用下， 以 正丁醇 、 水 为溶剂， 反应 1.5h， 以61%的产率得到(S)-8-{5-[3-methyl-4-(trifluoromethyl)phenyl]oxazol-2-ylamino}-1,2,3,4-tetrahydronaphthalen-2-ol
  参考文献：
  名称：

  TRPV1 ANTAGONISTS

  摘要：

  公式（I）中R1、R2、R4和W所定义的化合物是TRPV 1拮抗剂，具有中枢神经系统渗透性。还公开了包含这类化合物的组合物以及使用这类化合物和组合物治疗疾病和疾病的方法。

  公开号：

  US20090124666A1

文献信息

• 2-Aminooxazole derivatives for use as TRPV1 antagonists for treating i.a. pain, inflammation, neurodegenerative diseases or gastrointestinal diseases
  申请人：Abbott Laboratories

  公开号：EP2412372A1

  公开（公告）日：2012-02-01

  Compounds of formula (I) wherein R1, R2, R4, and W are defined in the description are TRPV1 antagonists with CNS penetration. Compositions comprising such compounds and methods for treating conditions and disorders using such compounds and compositions are also disclosed.

  其中 R1、R2、R4 和 W 在描述中定义的式 (I) 化合物是具有中枢神经系统渗透性的 TRPV1 拮抗剂。此外，还公开了包含此类化合物的组合物以及使用此类化合物和组合物治疗疾病的方法。
• Synthesis and biological evaluation of 5-substituted and 4,5-disubstituted-2-arylamino oxazole TRPV1 antagonists
  作者：Richard J. Perner、John R. Koenig、Stanley DiDomenico、Arthur Gomtsyan、Robert G. Schmidt、Chih-Hung Lee、Margaret C. Hsu、Heath A. McDonald、Donna M. Gauvin、Shailen Joshi、Teresa M. Turner、Regina M. Reilly、Philip R. Kym、Michael E. Kort

  DOI：10.1016/j.bmc.2010.04.099

  日期：2010.7

  The synthesis and structure-activity relationships of a series of 5-monosubstituted and 4,5-disubstituted 2-arylaminooxazoles as novel antagonists of the transient receptor potential vanilloid 1 (TRPV1) receptor are described. The 7-hydroxy group of the tetrahydronaphthyl moiety on the 2-amino substituent of the oxazole ring was important for obtaining excellent in vitro potency at the human TRPV1 receptor, while a variety of alkyl and phenyl substituents at the 4- and 5-positions of the oxazole ring were well tolerated and yielded potent TRPV1 antagonists. Despite excellent in vitro potency, the 5-monosubstituted compounds suffered from poor pharmacokinetics. It was found that 4,5-disubstitution on the oxazole ring was critical to the improvement of the overall pharmacokinetic profile of these analogues, which led to the discovery of compound (R)-27, a novel TRPV1 antagonist with good oral activity in preclinical animal models of pain. (C) 2010 Elsevier Ltd. All rights reserved.
• 2-AMINOOXAZOLE DERIVATIVES AS TRPVL ANTAGONISTS USEFUL FOR TREATING PAIN
  申请人：Abbott Laboratories

  公开号：EP2220059B1

  公开（公告）日：2011-08-03
• US7998993B2
  申请人：——

  公开号：US7998993B2

  公开（公告）日：2011-08-16