6-oxo-5,6-dihydrobenzo[e]pyrido[3,2-b][1,4]diazepine-11-carboxylic acid [2-(2-propyl-aminomethylpiperidin-1-yl)ethyl]amide | 528597-89-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯二氮卓类
• 英文名称: 6-oxo-5,6-dihydrobenzo[e]pyrido[3,2-b][1,4]diazepine-11-carboxylic acid [2-(2-propyl-aminomethylpiperidin-1-yl)ethyl]amide
• 英文别名: 6-oxo-5H,11H-benzo[e]pyrido[3,2-b][1,4]diazepine-11-carboxylic acid 2-[2-(propylaminomehtyl)piperidin-1-yl]ethylamide；6-oxo-N-[2-[2-(propylaminomethyl)piperidin-1-yl]ethyl]-5H-pyrido[2,3-b][1,4]benzodiazepine-11-carboxamide
• CAS: 528597-89-9
• 化学式: C₂₄H₃₂N₆O₂
• 分子量: 436.557
• InChiKey: JUKDBYFHSWPKBN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  89.6
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(3-溴丙基)苯二胺 、 6-oxo-5,6-dihydrobenzo[e]pyrido[3,2-b][1,4]diazepine-11-carboxylic acid [2-(2-propyl-aminomethylpiperidin-1-yl)ethyl]amide 在 N,N-二异丙基乙胺 作用下， 以 氯仿 为溶剂， 以24%的产率得到N-[2-[2-[[3-(1,3-dioxoisoindol-2-yl)propyl-propylamino]methyl]piperidin-1-yl]ethyl]-6-oxo-5H-pyrido[2,3-b][1,4]benzodiazepine-11-carboxamide
  参考文献：
  名称：

  Development of a New Type of Allosteric Modulator of Muscarinic Receptors:  Hybrids of the Antagonist AF-DX 384 and the Hexamethonio Derivative W84

  摘要：

  Various fragments of the hexamethonio-type allosteric agent W84 were linked to the secondary amino group of the muscarinic M-2 acetylcholine receptor-preferring antagonist AF-DX 384 to increase the area of attachment with the allosteric site. Addition of only the phthalimido moiety of W84 gave an allosteric enhancer of NMS binding. Thus, a new lead structure for the development of allosteric enhancers of NMS binding has been discovered.

  DOI：

  10.1021/jm031095t
• 作为产物：
  描述：

  5,11-二氢-6H-吡啶并[2,3-B][1,4]苯并二氮杂-6-酮 在 palladium on activated charcoal 氢气 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 、 甲苯 为溶剂， 20.0~110.0 ℃ 、5.0 MPa 条件下， 反应 20.76h， 生成 6-oxo-5,6-dihydrobenzo[e]pyrido[3,2-b][1,4]diazepine-11-carboxylic acid [2-(2-propyl-aminomethylpiperidin-1-yl)ethyl]amide
  参考文献：
  名称：

  对毒蕈碱型M 2受体具有亲和力的AFDX型化合物的新合成途径

  摘要：

  [3-（1,3-二氧代-1,3-二氢异吲哚-2-基）-丙基]二甲基-{6-[（1- {2-[（6-氧代-5,6-二氢-苯并[ e] ]吡啶并[3,2- b ] [1,4]二氮杂-11-羰基）氨基]乙基}哌啶-2-基-甲基）-丙基氨基]己基}溴化铵AFDX-384和称为拮抗剂结合的变构调节剂的W84部分，是从胡椒酸，邻苯二甲酸酐和3-氨基-2-氯吡啶开始的不同合成过程中合成的。这种新的微波辅助途径非常方便，可以修饰哌啶环，苯并二氮杂系统，邻苯二甲酰亚胺部分和连接环系统的链。产率和再现性令人满意。

  DOI：

  10.1016/s0040-4020(02)01623-x

文献信息

• Microwave-enhanced hydrogenations at medium pressure using a newly constructed reactor
  作者：Eberhard Heller、Werner Lautenschläger、Ulrike Holzgrabe

  DOI：10.1016/j.tetlet.2005.01.002

  日期：2005.2

  The newly constructed reactor for hydrogenations in microwave fields allows to work out the syntheses up to 25 bar. This is shown for the synthesis of intermediates of active agents. In order to demonstrate the superiority of the microwave-assisted hydrogenation, the reactions are compared with classical hydrogenations. The following reactions were carried out: dearomatization, debenzylation, azide hydrogenation and the hydrogenation of strychnine. (C) 2005 Elsevier Ltd. All rights reserved.
• A new synthetic route to compounds of the AFDX-type with affinity to muscarinic M2-receptor
  作者：Ulrike Holzgrabe、Eberhard Heller

  DOI：10.1016/s0040-4020(02)01623-x

  日期：2003.2

  do[3,2-b][1,4]diazepine-11-carbonyl)amino]ethyl}piperidin-2-yl-methyl)-propylamino]hexyl}ammonium bromide a hybride containing a fragment of the antagonist of muscarinic receptor AFDX-384 and a W84 moiety known as allosteric modulator of antagonist binding, was synthesized in a divergent synthesis starting from pipecolic acid, phthalic anhydride and 3-amino-2-chloropyridine. This new microwave assisted

  [3-（1,3-二氧代-1,3-二氢异吲哚-2-基）-丙基]二甲基-6-[（1- 2-[（6-氧代-5,6-二氢-苯并[ e] ]吡啶并[3,2- b ] [1,4]二氮杂-11-羰基）氨基]乙基}哌啶-2-基-甲基）-丙基氨基]己基}溴化铵AFDX-384和称为拮抗剂结合的变构调节剂的W84部分，是从胡椒酸，邻苯二甲酸酐和3-氨基-2-氯吡啶开始的不同合成过程中合成的。这种新的微波辅助途径非常方便，可以修饰哌啶环，苯并二氮杂系统，邻苯二甲酰亚胺部分和连接环系统的链。产率和再现性令人满意。
• Development of a New Type of Allosteric Modulator of Muscarinic Receptors:  Hybrids of the Antagonist AF-DX 384 and the Hexamethonio Derivative W84
  作者：Marion Mohr、Eberhard Heller、Ameneh Ataie、Klaus Mohr、Ulrike Holzgrabe

  DOI：10.1021/jm031095t

  日期：2004.6.1

  Various fragments of the hexamethonio-type allosteric agent W84 were linked to the secondary amino group of the muscarinic M-2 acetylcholine receptor-preferring antagonist AF-DX 384 to increase the area of attachment with the allosteric site. Addition of only the phthalimido moiety of W84 gave an allosteric enhancer of NMS binding. Thus, a new lead structure for the development of allosteric enhancers of NMS binding has been discovered.