[3-(4-bromo-2-methyl-2H-pyrazol-3-yl)-4-trifluoromethoxyphenyl]carbamic acid tert-butyl ester | 928655-41-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: [3-(4-bromo-2-methyl-2H-pyrazol-3-yl)-4-trifluoromethoxyphenyl]carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[3-(4-bromo-2-methylpyrazol-3-yl)-4-(trifluoromethoxy)phenyl]carbamate
• CAS: 928655-41-8
• 化学式: C₁₆H₁₇BrF₃N₃O₃
• 分子量: 436.228
• InChiKey: MVHGZAQRELCDPG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  65.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  [3-(2-methyl-2H-pyrazol-3-yl)-4-trifluoromethoxyphenyl]carbamic acid tert-butyl ester 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以89%的产率得到[3-(4-bromo-2-methyl-2H-pyrazol-3-yl)-4-trifluoromethoxyphenyl]carbamic acid tert-butyl ester
  参考文献：
  名称：

  Discovery of 1-[3-(4-Bromo-2-methyl-2H-pyrazol-3-yl)-4-methoxyphenyl]-3-(2,4-difluorophenyl)urea (Nelotanserin) and Related 5-Hydroxytryptamine_2A Inverse Agonists for the Treatment of Insomnia

  摘要：

  Insomnia affects it growing portion of the adult population in the U.S. Most current therapeutic approaches to insomnia primarily address sleep onset latency. Through the 5-hydroxytryptamine(2A) (5-HT2A) receptor, serotonin (5-HT) plays a role in the regulation of sleep architecture, and antagonists/inverse-agonists of 5-HT2A have been shown to enhance slow wave sleep (SWS). We describe here a series of 5-HT2A inverse-agonists that when dosed in rats, both consolidate the stages of NREM sleep, resulting in fewer awakenings, and increase a physiological measure of sleep intensity. These studies resulted in the discovery of 1-[3-(4-bromo-2-methyl-2H-pyrazol-3-yl)-4-methoxyphenyl]-3-(2,4-difluorophenyl)urea (Nelotanserin), it potent inverse-agonist of 5-HT2A that was advanced into clinical trials for the treatment of insomnia.

  DOI：

  10.1021/jm9007328