4-(3,5-dimethyl-benzyloxy)-phenylamine | 866357-57-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-(3,5-dimethyl-benzyloxy)-phenylamine
• 英文别名: 4-[(3,5-Dimethylphenyl)methoxy]aniline
• CAS: 866357-57-5
• 化学式: C₁₅H₁₇NO
• mdl: MFCD12856712
• 分子量: 227.306
• InChiKey: UHLRSDWTWTVHNA-UHFFFAOYSA-N

物化性质

• 沸点：
  385.0±32.0 °C(Predicted)
• 密度：
  1.087±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  35.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(3,5-dimethyl-benzyloxy)-phenylamine 、 N-叔丁氧羰基-2-氨基乙醛 在 三乙酰氧基硼氢化钠 作用下， 以 氯仿 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Discovery of N-(2-aminoethyl)-N-benzyloxyphenyl benzamides: New potent Trypanosoma brucei inhibitors

  摘要：

  A phenotypic screen of a compound library for antiparasitic activity on Trypanosoma brucei, the causative agent of Human African Trypanosomiasis (HAT), led to the identification of N-(2-aminoethyl)-N-phenyl benzamides as a starting point for hit-to-lead medicinal chemistry. Eighty two analogues were prepared, which led to the identification of a set of highly potent N-(2-aminoethyl)-N-benzyloxyphenyl benzamides with the most potent compound 73 having an in vitro EC50 = 0.001 mu M. The compounds displayed drug like properties when tested in a number of in vitro assays. Compound 73 was orally bioavailable and displayed good plasma and brain exposure in mice, cured 2 out of 3 mice infected with Trypanosoma brucei in acute model when dosed orally at 50 mg/kg once per day for 4 days. Given its potent antiparasitic properties and its ease of synthesis, compound 73 represents a potential lead for the development of drug to treat Human African Trypanosomiasis. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.11.019
• 作为产物：
  描述：

  3,5-二甲基溴苄 在 platinum on carbon 、 氢气 、 potassium carbonate 作用下， 以 乙酸乙酯 、 丙酮 为溶剂， 20.0~60.0 ℃ 、101.33 kPa 条件下， 反应 6.0h， 生成 4-(3,5-dimethyl-benzyloxy)-phenylamine
  参考文献：
  名称：

  Discovery of N-(2-aminoethyl)-N-benzyloxyphenyl benzamides: New potent Trypanosoma brucei inhibitors

  摘要：

  A phenotypic screen of a compound library for antiparasitic activity on Trypanosoma brucei, the causative agent of Human African Trypanosomiasis (HAT), led to the identification of N-(2-aminoethyl)-N-phenyl benzamides as a starting point for hit-to-lead medicinal chemistry. Eighty two analogues were prepared, which led to the identification of a set of highly potent N-(2-aminoethyl)-N-benzyloxyphenyl benzamides with the most potent compound 73 having an in vitro EC50 = 0.001 mu M. The compounds displayed drug like properties when tested in a number of in vitro assays. Compound 73 was orally bioavailable and displayed good plasma and brain exposure in mice, cured 2 out of 3 mice infected with Trypanosoma brucei in acute model when dosed orally at 50 mg/kg once per day for 4 days. Given its potent antiparasitic properties and its ease of synthesis, compound 73 represents a potential lead for the development of drug to treat Human African Trypanosomiasis. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.11.019

文献信息

• Substituted heteroaryl- and phenylsulfamoyl compounds
  申请人：Hamanaka S. Ernest

  公开号：US20050228015A1

  公开（公告）日：2005-10-13

  The present invention is directed at substituted heteroaryl- and phenylsulfamoyl compounds, pharmaceutical compositions containing such compounds and the use of such compounds as peroxisome proliferator activator receptor (PPAR) agonists. PPAR alpha activators, pharmaceutical compositions containing such compounds and the use of such compounds to elevate certain plasma lipid levels, including high density lipoprotein-cholesterol and to lower certain other plasma lipid levels, such as LDL-cholesterol and triglycerides and accordingly to treat diseases which are exacerbated by low levels of HDL cholesterol and/or high levels of LDL-cholesterol and triglycerides, such as atherosclerosis and cardiovascular diseases, in mammals, including humans. The compounds are also useful for the treatment of negative energy balance (NEB) and associated diseases in ruminants.

  本发明涉及取代杂环和苯基磺酰胺化合物，含有这些化合物的制药组合物以及将这些化合物用作过氧化物酶增殖子激活受体（PPAR）激动剂。PPARα激动剂，含有这些化合物的制药组合物以及使用这些化合物以提高某些血浆脂质水平，包括高密度脂蛋白胆固醇和降低其他某些血浆脂质水平，如低密度脂蛋白胆固醇和甘油三酯，从而治疗由低高密度脂蛋白胆固醇水平和/或高低密度脂蛋白胆固醇和甘油三酯水平加重的疾病，如动脉粥样硬化和心血管疾病，在哺乳动物，包括人类中。这些化合物还可用于治疗反能量平衡（NEB）和反刍动物相关疾病。
• Substituted Heteroaryl- and Phenylsulfamoyl Compounds
  申请人：Hamanaka S. Ernest

  公开号：US20060258723A1

  公开（公告）日：2006-11-16

  The present invention is directed at substituted heteroaryl and phenylsulfamoyl compounds, pharmaceutical compositions containing such compounds and the use of such compounds as peroxisome proliferator actuator receptor (PPAR) agonists. PPAR alpha activators, pharmaceutical compositions containing such compounds and the use of such compounds to elevate certain plasma lipid levels, including high density lipoprotein-cholesterol and to lower certain other plasma lipid levels, such as LDL-cholesterol and triglycerides and accordingly to treat diseases which are exacerbated by low levels of HDL cholesterol and/or high levels of LDL-cholesterol and triglycerides, such as atherosclerosis and cardiovascular diseases, in mammals, including humans. The compounds are also useful for the treatment of negative energy balance (NEB) and associated diseases in ruminants.

  本发明涉及取代杂环芳基和苯磺酰胺化合物，含有这种化合物的制药组合物以及将这种化合物用作过氧化物酶体增殖激活受体（PPAR）激动剂。PPARα激动剂，含有这种化合物的制药组合物以及将这种化合物用于升高某些血浆脂质水平，包括高密度脂蛋白胆固醇，并降低某些其他血浆脂质水平，如LDL胆固醇和甘油三酯，因此治疗低HDL胆固醇水平和/或高LDL胆固醇和甘油三酯水平加剧的疾病，例如动脉粥样硬化和心血管疾病，在哺乳动物，包括人类中使用。这些化合物也适用于治疗反式能量平衡（NEB）和反刍动物相关疾病。
• US7262318B2
  申请人：——

  公开号：US7262318B2

  公开（公告）日：2007-08-28