4-((2-aminophenyl)amino)butan-1-ol

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4-((2-aminophenyl)amino)butan-1-ol
• 英文别名: 2-(4-Hydroxybutylamino)phenylamine；4-(2-aminoanilino)butan-1-ol
• 化学式: C₁₀H₁₆N₂O
• 分子量: 180.25
• InChiKey: KZQKDSXRAYKAPM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  58.3
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-((2-aminophenyl)amino)butan-1-ol 在 盐酸 、 sodium hydride 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 1'-((1-(4-hydroxybutyl)-1H-benzo[d]imidazol-2-yl)methyl)spiro[cyclopropane-1,3'-indolin]-2'-one
  参考文献：
  名称：

  3,3'-螺[氮杂环丁烷] -2-氧-吲哚啉衍生物作为融合抑制剂治疗RSV感染的发现。

  摘要：

  合成了一系列新的3,3'-螺环-2-氧-二氢吲哚衍生物，并在基于细胞的试验和动物模型中评估了其对呼吸道合胞病毒（RSV）的作用。广泛的构效关系研究导致了铅化合物14h，其在体外的效价极好，EC50值为0.8 nM，在小鼠中的口服生物利用度为71％。在RVS感染的小鼠攻击模型中，口服50 mg / kg剂量后14h表现出优异的功效，肺中的3.9log RSV病毒载量减少。

  DOI：

  10.1021/acsmedchemlett.7b00418
• 作为产物：
  描述：

  4-((2-nitrophenyl)amino)butan-1-ol 在 5%-palladium/activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 12.0h， 以14.7 g的产率得到4-((2-aminophenyl)amino)butan-1-ol
  参考文献：
  名称：

  3,3'-螺[氮杂环丁烷] -2-氧-吲哚啉衍生物作为融合抑制剂治疗RSV感染的发现。

  摘要：

  合成了一系列新的3,3'-螺环-2-氧-二氢吲哚衍生物，并在基于细胞的试验和动物模型中评估了其对呼吸道合胞病毒（RSV）的作用。广泛的构效关系研究导致了铅化合物14h，其在体外的效价极好，EC50值为0.8 nM，在小鼠中的口服生物利用度为71％。在RVS感染的小鼠攻击模型中，口服50 mg / kg剂量后14h表现出优异的功效，肺中的3.9log RSV病毒载量减少。

  DOI：

  10.1021/acsmedchemlett.7b00418

文献信息

• Novel substituted piperidines, pharmaceutical compositions containing these compounds, their use and processes for the preparation thereof
  申请人：Boehringer ingelheim Pharma GmbH & Co.

  公开号：US20030236282A1

  公开（公告）日：2003-12-25

  The present invention relates to substituted piperidines of general formula 1 wherein R, R 2 to R 5 , A, X, Z and n are defined as in claim 1, the tautomers, diastereomers, enantiomers, mixtures and salts thereof, particularly the physiologically acceptable salts thereof with inorganic or organic acids or bases which have valuable pharmacological properties, particularly CGRP-antagonistic properties, pharmaceutical compositions containing these compounds, the use thereof and processes for the preparation thereof.

  本发明涉及一般式1的取代哌啶，其中R，R2至R5，A，X，Z和n的定义如权利要求1中所述，其互变异构体、对映异构体、立体异构体、混合物及其盐，特别是其与具有有价值的药理学性质，特别是CGRP-拮抗性能的无机或有机酸或碱的生理上可接受的盐，含有这些化合物的制药组合物，其用途以及其制备方法。
• Dihydropyridine antiallergic and antiinflammatory agents
  申请人：Pfizer Inc.

  公开号：US04904671A1

  公开（公告）日：1990-02-27

  4-Aryl-2,6-disubstituted-3,5-dicarbamyl-1,4-dihydropyridines and 4-Aryl-2,6-disubstituted-3-alkoxycarbonyl-5-carbamyl-1,4-dihydropyridines as antiallergy and antiinflammatory agents.

  4-芳基-2,6-二取代-3,5-二氨基甲酰基-1,4-二氢吡啶和4-芳基-2,6-二取代-3-烷氧羰基-5-氨基甲酰基-1,4-二氢吡啶作为抗过敏和抗炎药物。
• Dihydropyridines, their preparation and their use as PAF-antagonists
  申请人：Pfizer Limited

  公开号：EP0330327A2

  公开（公告）日：1989-08-30

  Dihydropyridine PAF antagonists useful in the treatment of allergic and inflammatory conditions and having the formula:- where Ar is an optionally substituted phenyl group; R and R¹ and each C₁-C₄ alkyl or aryl; R² and R³ are each H or C₁-C₆ alkyl or may be joined together to form with the N atom to which they are attached certain heterocyclic groups, or R² is H or C₁-C₄ alkyl and R³ is either (a) C₃-C₇ cycloalkyl, aryl, indanyl or heteroaryl, or (b) a C₁-C₄ alkyl group substituted by one or two substituents each selected from C₃-C₇ cycloalkyl, C₁-C₄ alkoxycarbonyl, aryl and heteroaryl; X is O or NH; Y is -(CH₂)m- where m is 4 or 5 or where n is 1 or 2 and p is 0 or 1; and Z is 5- or 6-membered nitrogen-containing heterocyclic group optionally benzo-fused or fused to a further heterocyclic group.

  二氢吡啶类 PAF 拮抗剂，可用于治疗过敏性和炎症性病症，其式如下： - 其中 Ar 为任选取代的苯基 其中 Ar 是任选取代的苯基； R 和 R¹ 分别是 C₁-C₄ 烷基或芳基； R²和R³各自为H或C₁-C₆烷基，或可连接在一起，与所连接的N原子形成某些杂环基团、 或 R² 是 H 或 C₁-C₄ 烷基，R³ 是 (a) C₃-C₇ 环烷基、芳基、茚满基或杂芳基、或 (b) 被一个或两个各自选自 C₃-C₇ 环烷基、C₁-C₄ 烷氧基羰基、芳基和杂芳基的取代基取代的 C₁-C₄ 烷基； X 是 O 或 NH Y 是-(CH₂)m-，其中 m 是 4 或 5，或 其中 n 为 1 或 2，p 为 0 或 1； Z 是 5 或 6 元含氮杂环基团，可选择与苯并合或与另一个杂环基团并合。
• RETRACTED: A room temperature copper catalyzed N-selective arylation of β-amino alcohols with iodoanilines and aryl iodides
  作者：Priyabrata Das、Jef K. De Brabander

  DOI：10.1016/j.tet.2013.04.128

  日期：2013.9

  An efficient method is described for the synthesis of N-(2-aminophenyl)-2-hydroxyethylamines via a copper catalyzed N-selective arylation of beta-amino alcohols with iodoanilines. The corresponding coupling products are useful intermediates for the synthesis of a variety of N-2-hydroxyethyl-substituted benzimidazoles, benzimidazolones, and iminobenzimidazoles. We found that 2-iodoaniline only arylates certain amino alcohols but not amines lacking a hydroxyl group. We also demonstrate the arylation of sterically demanding beta-amino alcohols, such as ephedrine and prolinol with aryl iodides at room temperature. (C) 2013 Elsevier Ltd. All rights reserved.
• Respiratory syncytial virus fusion inhibitors. Part 7: Structure–activity relationships associated with a series of isatin oximes that demonstrate antiviral activity in vivo
  作者：Ny Sin、Brian L. Venables、Keith D. Combrink、H. Belgin Gulgeze、Kuo-Long Yu、Rita L. Civiello、Jan Thuring、X. Alan Wang、Zheng Yang、Lisa Zadjura、Anthony Marino、Kathleen F. Kadow、Christopher W. Cianci、Junius Clarke、Eugene V. Genovesi、Ivette Medina、Lucinda Lamb、Mark Krystal、Nicholas A. Meanwell

  DOI：10.1016/j.bmcl.2009.06.030

  日期：2009.8

  A series of bezimidazole-isatin oximes were prepared and profiled as inhibitors of respiratory syncytial virus (RSV) replication in cell culture. Structure-activity relationship studies were directed toward optimization of antiviral activity, cell permeability and metabolic stability in human liver micorosomes (HLM). Parallel combinatorial synthetic chemistry was employed to functionalize isatin oximes via O-alkylation which quickly identified a subset of small, lipophilic substituents that established good potency for the series. Further optimization of the isatin oxime derivatives focused on introduction of nitrogen atoms to the isatin phenyl ring to provide a series of aza-isatin oximes with significantly improved PK properties. Several aza-isatin oximes analogs displayed targeted metabolic stability in HLM and permeability across a confluent monolayer of CaCo-2 cells. These studies identified several compounds, including 18i, 18j and 18n that demonstrated antiviral activity in the BALB/c mouse model of RSV infection following oral dosing. (C) 2009 Elsevier Ltd. All rights reserved.