1-(3-bromopropyl)-4- (trifluoromethoxy)benzene | 1093172-94-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-(3-bromopropyl)-4- (trifluoromethoxy)benzene
• 英文别名: 1-(3-Bromopropyl)-4-trifluoromethoxybenzene；1-(3-bromopropyl)-4-(trifluoromethoxy)benzene
• CAS: 1093172-94-1
• 化学式: C₁₀H₁₀BrF₃O
• 分子量: 283.088
• InChiKey: ALTBCFMOMPRTQJ-UHFFFAOYSA-N

物化性质

• 沸点：
  235.9±35.0 °C(Predicted)
• 密度：
  1.471±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(3-bromopropyl)-4- (trifluoromethoxy)benzene 、 二苯乙醇酸-3-奎宁环酯 以 1,4-二氧六环 为溶剂， 反应 144.0h， 以57%的产率得到3-(2-hydroxy-2,2-diphenylacetoxy)-1-{3-[4-(trifluoromethoxy)phenyl]propyl}-1-azoniabicyclo[2.2.2]octane bromide
  参考文献：
  名称：

  Chemical modification-mediated optimisation of bronchodilatory activity of mepenzolate, a muscarinic receptor antagonist with anti-inflammatory activity

  摘要：

  The treatment for patients with chronic obstructive pulmonary disease (COPD) usually involves a combination of anti-inflammatory and bronchodilatory drugs. We recently found that mepenzolate bromide (1) and its derivative, 3-(2-hydroxy-2, 2-diphenylacetoxy)-1-(3-phenoxypropyl)-1-azoniabicyclo[2.2.2] octane bromide (5), have both anti-inflammatory and bronchodilatory activities. We chemically modified 5 with a view to obtain derivatives with both anti-inflammatory and longer-lasting bronchodilatory activities. Among the synthesized compounds, (R)-(-)-12 ((R)-3-(2-hydroxy-2,2-diphenylacetoxy)-1-(3-phenylpropyl)-1-azoniabicyclo[ 2.2.2] octane bromide) showed the highest affinity in vitro for the human muscarinic M3 receptor (hM(3)R). Compared to 1 and 5, (R)-(-)-12 exhibited longer-lasting bronchodilatory activity and equivalent anti-inflammatory effect in mice. The long-term intratracheal administration of (R)-(-)-12 suppressed porcine pancreatic elastase-induced pulmonary emphysema in mice, whereas the same procedure with a long-acting muscarinic antagonist used clinically (tiotropium bromide) did not. These results suggest that (R)-(-)-12 might be therapeutically beneficial for use with COPD patients given the improved effects seen against both inflammatory pulmonary emphysema and airflow limitation in this animal model.

  DOI：

  10.1016/j.bmc.2019.06.016
• 作为产物：
  描述：

  3-(4-(三氟甲氧基)苯基)丙酸 在 四溴化碳 、 dimethyl sulfide borane 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 36.0h， 生成 1-(3-bromopropyl)-4- (trifluoromethoxy)benzene
  参考文献：
  名称：

  Chemical modification-mediated optimisation of bronchodilatory activity of mepenzolate, a muscarinic receptor antagonist with anti-inflammatory activity

  摘要：

  The treatment for patients with chronic obstructive pulmonary disease (COPD) usually involves a combination of anti-inflammatory and bronchodilatory drugs. We recently found that mepenzolate bromide (1) and its derivative, 3-(2-hydroxy-2, 2-diphenylacetoxy)-1-(3-phenoxypropyl)-1-azoniabicyclo[2.2.2] octane bromide (5), have both anti-inflammatory and bronchodilatory activities. We chemically modified 5 with a view to obtain derivatives with both anti-inflammatory and longer-lasting bronchodilatory activities. Among the synthesized compounds, (R)-(-)-12 ((R)-3-(2-hydroxy-2,2-diphenylacetoxy)-1-(3-phenylpropyl)-1-azoniabicyclo[ 2.2.2] octane bromide) showed the highest affinity in vitro for the human muscarinic M3 receptor (hM(3)R). Compared to 1 and 5, (R)-(-)-12 exhibited longer-lasting bronchodilatory activity and equivalent anti-inflammatory effect in mice. The long-term intratracheal administration of (R)-(-)-12 suppressed porcine pancreatic elastase-induced pulmonary emphysema in mice, whereas the same procedure with a long-acting muscarinic antagonist used clinically (tiotropium bromide) did not. These results suggest that (R)-(-)-12 might be therapeutically beneficial for use with COPD patients given the improved effects seen against both inflammatory pulmonary emphysema and airflow limitation in this animal model.

  DOI：

  10.1016/j.bmc.2019.06.016

文献信息

• FLAVIN DERIVATIVES
  申请人：Coish Philip D. G.

  公开号：US20130029980A1

  公开（公告）日：2013-01-31

  The present invention relates novel flavin derivatives, their use and compositions for use as riboswitch ligands and/or anti-infectives.

  本发明涉及新型黄素衍生物，其用途和组合物，用作核糖开关配体和/或抗感染剂。
• Amine compound and pharmaceutical use thereof
  申请人：Mitsubishi Tanabe Pharma Corporation

  公开号：US08129361B2

  公开（公告）日：2012-03-06

  Provided is a novel amine compound represented by the following formula (I) having a superior peripheral blood lymphocyte decreasing action and superior in the immunosuppressive action, rejection suppressive action and the like, which shows decreased side effects of, for example, bradycardia and the like, or a pharmaceutically acceptable acid addition salt thereof, or a hydrate thereof, or a solvate thereof. wherein each symbol is as defined in the specification.

  提供的是一种新型胺类化合物，其化学式如下（I），具有卓越的外周血淋巴细胞降低作用和免疫抑制作用，抗排异作用等方面表现出降低副作用的优点，例如心动过缓等，或其药学上可接受的酸盐，或其水合物，或其溶剂化物。 其中，每个符号如规范中所定义。
• AMINE COMPOUND AND PHARMACEUTICAL USE THEREOF
  申请人：Mitsubishi Tanabe Pharma Corporation

  公开号：EP2168944B1

  公开（公告）日：2016-05-11
• US8129361B2
  申请人：——

  公开号：US8129361B2

  公开（公告）日：2012-03-06
• Chemical modification-mediated optimisation of bronchodilatory activity of mepenzolate, a muscarinic receptor antagonist with anti-inflammatory activity
  作者：Yasunobu Yamashita、Ken-ichiro Tanaka、Naoki Yamakawa、Teita Asano、Yuki Kanda、Ayaka Takafuji、Masahiro Kawahara、Mitsuko Takenaga、Yoshifumi Fukunishi、Tohru Mizushima

  DOI：10.1016/j.bmc.2019.06.016

  日期：2019.8

  The treatment for patients with chronic obstructive pulmonary disease (COPD) usually involves a combination of anti-inflammatory and bronchodilatory drugs. We recently found that mepenzolate bromide (1) and its derivative, 3-(2-hydroxy-2, 2-diphenylacetoxy)-1-(3-phenoxypropyl)-1-azoniabicyclo[2.2.2] octane bromide (5), have both anti-inflammatory and bronchodilatory activities. We chemically modified 5 with a view to obtain derivatives with both anti-inflammatory and longer-lasting bronchodilatory activities. Among the synthesized compounds, (R)-(-)-12 ((R)-3-(2-hydroxy-2,2-diphenylacetoxy)-1-(3-phenylpropyl)-1-azoniabicyclo[ 2.2.2] octane bromide) showed the highest affinity in vitro for the human muscarinic M3 receptor (hM(3)R). Compared to 1 and 5, (R)-(-)-12 exhibited longer-lasting bronchodilatory activity and equivalent anti-inflammatory effect in mice. The long-term intratracheal administration of (R)-(-)-12 suppressed porcine pancreatic elastase-induced pulmonary emphysema in mice, whereas the same procedure with a long-acting muscarinic antagonist used clinically (tiotropium bromide) did not. These results suggest that (R)-(-)-12 might be therapeutically beneficial for use with COPD patients given the improved effects seen against both inflammatory pulmonary emphysema and airflow limitation in this animal model.