3-(3-(diethylamino)propoxy)aniline

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-(3-(diethylamino)propoxy)aniline
• 英文别名: 3-[3-(diethylamine)propoxy]benzenamine；N-[3-(3-aminophenoxy)propyl]-N,N-diethylamine；3-[3-(diethylamino)propoxy]aniline
• 化学式: C₁₃H₂₂N₂O
• mdl: MFCD11593615
• 分子量: 222.33
• InChiKey: ATRJBSNVIQVCQB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.538
• 拓扑面积：
  38.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  嘧啶,2-氯-4,6-二(4-氯苯基)- 、 3-(3-(diethylamino)propoxy)aniline 在 盐酸 作用下， 以 1,4-二氧六环 、 正丁醇 为溶剂， 反应 1.0h， 以52%的产率得到4,6-bis(4-chlorophenyl)-N-(3-(3-(diethylamino)propoxy)phenyl)pyrimidin-2-amine
  参考文献：
  名称：

  Fine tuning of 4,6-bisphenyl-2-(3-alkoxyanilino)pyrimidine focusing on the activity-sensitive aminoalkoxy moiety for a therapeutically useful inhibitor of receptor for advanced glycation end products (RAGE)

  摘要：

  Through the fine tuning of the activity-sensitive aminoalkoxy moiety of 4,6-bisphenyl-2-(3-alkoxyanilino)pyrimidine as a novel inhibitor of the receptor for advanced glycation end products (RAGE), the tertiary amine was elucidated as an essential part associated with RAGE inhibition. On the basis of this finding, a 3-(N,N-dimethylamino)pyrrolidine analog 12o was identified as a therapeutically useful RAGE inhibitor with improved activity and solubility. Molecular modeling studies predicted that the improved inhibitory activity is induced by additional hydrogen bonds between the nitrogen atom of the pyrrolidine ring and Arg48 and by an interaction between the dimethylamino-substituent of the pyrrolidine moiety and a relatively hydrophobic groove in the RAGE binding site. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.12.003
• 作为产物：
  描述：

  3-二乙氨基-1-丙醇 在 tin(II) chloride dihdyrate 、 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 6.0h， 生成 3-(3-(diethylamino)propoxy)aniline
  参考文献：
  名称：

  Fine tuning of 4,6-bisphenyl-2-(3-alkoxyanilino)pyrimidine focusing on the activity-sensitive aminoalkoxy moiety for a therapeutically useful inhibitor of receptor for advanced glycation end products (RAGE)

  摘要：

  Through the fine tuning of the activity-sensitive aminoalkoxy moiety of 4,6-bisphenyl-2-(3-alkoxyanilino)pyrimidine as a novel inhibitor of the receptor for advanced glycation end products (RAGE), the tertiary amine was elucidated as an essential part associated with RAGE inhibition. On the basis of this finding, a 3-(N,N-dimethylamino)pyrrolidine analog 12o was identified as a therapeutically useful RAGE inhibitor with improved activity and solubility. Molecular modeling studies predicted that the improved inhibitory activity is induced by additional hydrogen bonds between the nitrogen atom of the pyrrolidine ring and Arg48 and by an interaction between the dimethylamino-substituent of the pyrrolidine moiety and a relatively hydrophobic groove in the RAGE binding site. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.12.003

文献信息

• Carboxamide derivatives as therapeutic agents
  申请人：——

  公开号：US20020193432A1

  公开（公告）日：2002-12-19

  This invention provides certain compounds, methods of their preparation, pharmaceutical compositions comprising the compounds, and their use in treating human or animal disorders. The compounds of the invention are useful as modulators of the interaction between the receptor for advanced glycated end products (RAGE) and its ligands, such as advanced glycated end products (AGEs), S100/calgranulin/EN-RAGE, &bgr;-amyloid and amphoterin, and for the management, treatment, control, or as an adjunct treatment for diseases in humans caused by RAGE. Such diseases or disease states include acute and chronic inflammation, the development of diabetic late complications such as increased vascular permeability, nephropathy, atherosclerosis, and retinopathy, the development of Alzheimer's disease, erectile dysfunction, and tumor invasion and metastasis.

  这项发明提供了某些化合物、其制备方法、包括这些化合物的药物组合物以及它们在治疗人类或动物疾病中的用途。该发明的化合物可用作调节高级糖基化终产物受体（RAGE）与其配体之间相互作用的调节剂，这些配体包括高级糖基化终产物（AGEs）、S100/calgranulin/EN-RAGE、β-淀粉样蛋白和amphoterin，用于管理、治疗、控制或作为辅助治疗人类因RAGE引起的疾病。这些疾病或疾病状态包括急性和慢性炎症、糖尿病后期并发症的发展，如增加的血管通透性、肾病、动脉粥样硬化和视网膜病变，阿尔茨海默病的发展、勃起功能障碍以及肿瘤侵袭和转移。
• Design, synthesis and biological evaluation of selected 3-[3-(amino) propoxy] benzenamines as acetylcholinesterase inhibitors
  作者：Ruchi Malik、Richa Gupta、Shubham Srivastava、Bhanwar Singh Choudhary、Manish Sharma

  DOI：10.1080/07391102.2016.1220330

  日期：2017.8.18

  relaxant, analgesic and anticonvulsant activities). Compound 3-[3-(imidazolo)propoxy]benzenamine has shown significant dose-dependent (1 and 3 mg/kg) memory enhancing activity, while 3-[3-(pyrrolidino)propoxy]benzenamine also showed activity equivalent to reference drug piracetam at 1 mg/kg. Both compounds 3-[3-(pyrrolidino)propoxy]benzenamine and 3-[3-(imidazolo)propoxy]benzenamine were also found to show

  本文描述了一系列的3- [3-（氨基）丙氧基]苯甲胺类作为乙酰胆碱酯酶抑制剂的设计，合成和生物学评估，以小鼠为模型，吡拉西坦为参比药物。这些化合物的结构通过光谱分析确认，并使用升高的迷宫测试和乙酰胆碱酯酶抑制试验测试化合物的记忆增强活性。合成化合物的抑制范围为8.99至28.31μM。与吡乙酰胺相比，合成的化合物在1 mg / kg的条件下具有比吡乙酰胺更高或相当的保留率，并且没有其他与CNS相关的活性（运动和肌肉松弛，镇痛和抗惊厥活性）。化合物3- [3-（咪唑基）丙氧基]苯胺已显示出显着的剂量依赖性（1和3 mg / kg）记忆增强活性，而3- [3-（吡咯烷基）丙氧基]苯甲胺也显示出与参考药物吡拉西坦相当的活性，为1 mg / kg。还发现化合物3- [3-（吡咯烷基）丙氧基]苯胺和3- [3-（咪唑基）丙氧基]苯胺都显示出IC对AChE的抑制作用50值为8.99和17.87μM。为
• [EN] MONO- AND BICYCLIC AZOLE DERIVATIVES THAT INHIBIT THE INTERACTION OF LIGANDS WITH RAGE<br/>[FR] DERIVES DE L'AZOLE ET DERIVES BICYCLIQUES FUSIONNES DE L'AZOLE, AGENTS THERAPEUTIQUES
  申请人：TRANSTECH PHARMA INC

  公开号：WO2003075921A2

  公开（公告）日：2003-09-18

  This invention provides certain compounds of formula I wherein A1 is O, S or -N(R2)-, methods of their preparation, pharmaceutical compositions comprising the compounds, and their use in treating human or animal disorders. The compounds of the invention are useful as modulators of the interaction between the receptor for advanced glycated end products (RAGE) and its ligands, such as advanced glycated end products (AGEs), S100/calgranulin/EN-RAGE, β-amyloid and amphoterin, and for the management, treatment, control, or as an adjunct treatment for diseases in humans caused by RAGE. Such diseases or disease states include acute and chronic inflammation, the development of diabetic late complications such as increased vascular permeability, nephropathy, atherosclerosis, and retinopathy, the development of Alzheimer’s disease, erectile dysfunction, and tumor invasion and metastasis.

  本发明提供了一些公式I的化合物，其中A1是O，S或-N（R2）-，它们的制备方法，包括这些化合物的制药组合物，以及它们在治疗人类或动物疾病方面的用途。本发明的化合物可作为高级糖基化终产物（AGEs），S100 / calgranulin / EN-RAGE，β-淀粉样蛋白和amphoterin等配体与其受体（RAGE）之间相互作用的调节剂，并用于治疗由RAGE引起的人类疾病的管理，治疗，控制或辅助治疗。这些疾病或疾病状态包括急性和慢性炎症，糖尿病晚期并发症的发展，如增加的血管通透性，肾病，动脉粥样硬化和视网膜病变，阿尔茨海默病的发展，勃起功能障碍以及肿瘤侵袭和转移。
• Azole derivatives and fused bicyclic azole derivatives as therapeutic agents
  申请人：——

  公开号：US20040082542A1

  公开（公告）日：2004-04-29

  This invention provides certain compounds, methods of their preparation, pharmaceutical compositions comprising the compounds, and their use in treating human or animal disorders. The compounds of the invention are useful as modulators of the interaction between the receptor for advanced glycated end products (RAGE) and its ligands, such as advanced glycated end products (AGEs), S100/calgranulin/EN-RAGE, &bgr;-amyloid and amphoterin, and for the management, treatment, control, or as an adjunct treatment for diseases in humans caused by RAGE. Such diseases or disease states include acute and chronic inflammation, the development of diabetic late complications such as increased vascular permeability, nephropathy, atherosclerosis, and retinopathy, the development of Alzheimer's disease, erectile dysfunction, and tumor invasion and metastasis.

  本发明提供了某些化合物、它们的制备方法、包含这些化合物的药物组合物以及它们在治疗人类或动物疾病中的应用。本发明的化合物可用作高级糖基化终产物受体（RAGE）及其配体（如高级糖基化终产物（AGEs）、S100/calgranulin/EN-RAGE、β-淀粉样蛋白和amphoterin）之间相互作用的调节剂，并用于治疗由RAGE引起的人类疾病的管理、治疗、控制或作为辅助治疗。这些疾病或疾病状态包括急性和慢性炎症、糖尿病晚期并发症的发展（如增加的血管通透性、肾病、动脉粥样硬化和视网膜病变）、阿尔茨海默病的发展、勃起功能障碍以及肿瘤侵袭和转移。
• Carboxamide Derivatives as Therapeutic Agents
  申请人：Mjalli M.M. Adnan

  公开号：US20080119512A1

  公开（公告）日：2008-05-22

  This invention provides certain compounds, methods of their preparation, pharmaceutical compositions comprising the compounds, and their use in treating human or animal disorders. The compounds of the invention are useful as modulators of the interaction between the receptor for advanced glycated end products (RAGE) and its ligands, such as advanced glycated end products (AGEs), S100/calgranulin/EN-RAGE, β-amyloid and amphoterin, and for the management, treatment, control, or as an adjunct treatment for diseases in humans caused by RAGE. Such diseases or disease states include acute and chronic inflammation, the development of diabetic late complications such as increased vascular permeability, nephropathy, atherosclerosis, and retinopathy, the development of Alzheimer's disease, erectile dysfunction, and tumor invasion and metastasis.

  这项发明提供了某些化合物、它们的制备方法、包含这些化合物的药物组合物以及它们在治疗人类或动物疾病中的应用。该发明的化合物可用作高级糖基化终产物（AGEs）、S100/calgranulin/EN-RAGE、β-淀粉样蛋白和amphoterin等配体与其受体——高级糖基化终产物受体（RAGE）之间相互作用的调节剂，并可用于管理、治疗、控制或作为辅助治疗人类因RAGE引起的疾病。这些疾病或疾病状态包括急性和慢性炎症、糖尿病晚期并发症的发展，如增加的血管通透性、肾病、动脉硬化和视网膜病变，阿尔茨海默病的发展、勃起功能障碍以及肿瘤侵袭和转移。