4-(4-methoxybenzyl)amino-3-nitrobenzoic acid | 312921-93-0

• 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: 4-(4-methoxybenzyl)amino-3-nitrobenzoic acid
• 英文别名: 4-[(4-Methoxyphenyl)methylamino]-3-nitrobenzoic acid
• CAS: 312921-93-0
• 化学式: C₁₅H₁₄N₂O₅
• 分子量: 302.287
• InChiKey: FUMPLRDMJLKRIV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  104
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-(4-methoxybenzyl)amino-3-nitrobenzoic acid 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 20.0 ℃ 、101.32 kPa 条件下， 反应 3.0h， 生成 3-Amino-4-(4-methoxy-benzylamino)-benzoic acid
  参考文献：
  名称：

  1-Alkyl-benzotriazole-5-carboxylic Acids Are Highly Selective Agonists of the Human Orphan G-Protein-Coupled Receptor GPR109b

  摘要：

  I-Substituted benzotriazole carboxylic acids have been identified as the first reported examples of selective small-molecule agonists of the human orphan G-protein-coupled receptor GPR109b (HM74), a low-affinity receptor for the HDL-raising drug niacin. No activity was observed at the highly homologous high-affinity macin receptor GPR109a (HM74A). The high degree of selectivity was attributed to a difference in the amino acid sequence adjacent to a key arginine-ligand interaction allowing somewhat larger ligands to be tolerated by GPR109b.

  DOI：

  10.1021/jm051099t
• 作为产物：
  描述：

  [4-[[4-[(4-heptan-3-yl-6-oxo-1H-pyrimidin-2-yl)carbamoylamino]phenyl]methoxy]phenyl]methyl 4-[(4-methoxyphenyl)methylamino]-3-nitrobenzoate 在 三氟乙酸 作用下， 反应 1.5h， 以86%的产率得到4-(4-methoxybenzyl)amino-3-nitrobenzoic acid
  参考文献：
  名称：

  一种利用氢键进行有机合成的新纯化方法

  摘要：

  报道了一种基于四重氢键相互作用的新后处理和纯化方法。含有氢键亲和标签的底物 - 无论是直接连接还是通过可切割的接头 - 都可以方便地从反应混合物中分离出来，并使用含有自互补亲和标签的树脂进行纯化。通过这种基于氢键的亲和分离方案，成功纯化了几种 Ugi 产物和亲核芳香取代产物。

  DOI：

  10.1002/ejoc.200700242

文献信息

• [EN] BENZOTRIAZOLES AND METHODS OF PROPHYLAXIS OR TREATMENT OF METABOLIC-RELATED DISORDERS THEREOF<br/>[FR] BENZOTRIAZOLES ET PROCEDES DE PREVENTION OU DE TRAITEMENT DES TROUBLES METABOLIQUE
  申请人：ARENA PHARM INC

  公开号：WO2004041274A1

  公开（公告）日：2004-05-21

  The present invention relates to certain benzotriazole carboxylic acid or ester derivatives of Formula (I), pharmaceutically acceptable salts and solvates thereof, which exhibit useful pharmaceutical properties, for example, as agonists for the GPCR referred to as hRUP38. Also provided by the present invention are pharmaceutical compositions containing compounds of the invention, and methods of using the compounds and compositions of the invention in the prophylaxis or treatment of metabolic-related disorders, including dyslipidemia, atherosclerosis, coronary heart disease, insulin resistance, type 2 diabetes, Syndrome-X and the like. In addition, the present invention also provides for the use of the compounds of the invention in combination with other active agents such as those belonging to the class of -glucosidase inhibitors, aldose reductase inhibitors, biguanides, HMG-CoA reductase inhibitors, squalene synthesis inhibitors, fibrates, LDL catabolism enhancers, angiotensin converting enzyme (ACE) inhibitors, insulin secretion enhancers and the like.

  本发明涉及公式（I）的若干苯并三唑羧酸或酯衍生物，其药学上可接受的盐和溶剂化物，具有有用的药理特性，例如作为称为hRUP38的GPCR激动剂。本发明还提供了含有本发明化合物的药物组合物，以及使用本发明化合物和组合物在预防或治疗代谢相关疾病，包括血脂异常、动脉粥样硬化、冠心病、胰岛素抵抗、2型糖尿病、综合征X等方面的方法。此外，本发明还提供了将本发明化合物与属于-葡萄糖苷酶抑制剂、醛还原酶抑制剂、双胍类、HMG-CoA还原酶抑制剂、角鲨烷合成抑制剂、非酯类、LDL降解增强剂、血管紧张素转化酶（ACE）抑制剂、胰岛素分泌增强剂等类别的其他活性剂联合使用的方法。
• Benzotriazoles and methods of prophylaxis or treatment of metabolic-related disorders thereof
  申请人：Semple Graeme

  公开号：US20060122240A1

  公开（公告）日：2006-06-08

  The present invention relates to certain benzotriazole carboxylic acid or ester derivatives of Formula (I), pharmaceutically acceptable salts and solvates thereof, which exhibit useful pharmaceutical properties, for example, as agonists for the GPCR referred to as hRUP38. Also provided by the present invention are pharmaceutical compositions containing compounds of the invention, and methods of using the compounds and compositions of the invention in the prophylaxis or treatment of metabolic-related disorders, including dyslipidemia, atherosclerosis, coronary heart disease, insulin resistance, type 2 diabetes, Syndrome-X and the like. In addition, the present invention also provides for the use of the compounds of the invention in combination with other active agents such as those belonging to the class of -glucosidase inhibitors, aldose reductase inhibitors, biguanides, HMG-CoA reductase inhibitors, squalene synthesis inhibitors, fibrates, LDL catabolism enhancers, angiotensin converting enzyme (ACE) inhibitors, insulin secretion enhancers and the like.

  本发明涉及公式（I）的某些苯并三唑羧酸或酯衍生物，其药学上可接受的盐和溶剂，具有有用的药理特性，例如作为被称为hRUP38的GPCR的激动剂。本发明还提供了含有该发明化合物的制药组合物，以及使用该发明化合物和组合物在预防或治疗代谢相关疾病，包括脂质代谢异常、动脉粥样硬化、冠心病、胰岛素抵抗、2型糖尿病、综合征X等方面的方法。此外，本发明还提供了将该发明化合物与属于-葡萄糖苷酶抑制剂、醛糖还原酶抑制剂、双胍类药物、HMG-CoA还原酶抑制剂、角鲨烷合成抑制剂、纤维酸类、低密度脂蛋白降解增强剂、血管紧张素转换酶（ACE）抑制剂、胰岛素分泌增强剂等类别的其他活性剂一起使用的方法。