N'-benzyl-N'-propyl-propane-1,3-diamine | 874813-66-8

• 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: N'-benzyl-N'-propyl-propane-1,3-diamine
• 英文别名: N1-benzyl-N1-propylpropane-1,3-diamine；N'-benzyl-N'-propylpropane-1,3-diamine
• CAS: 874813-66-8
• 化学式: C₁₃H₂₂N₂
• 分子量: 206.331
• InChiKey: RPCAZXDMNFBHKB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  29.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N'-benzyl-N'-propyl-propane-1,3-diamine 、 6-氯-2-甲氧基-9-苯氧基吖啶 以 二甲基亚砜 为溶剂， 反应 4.0h， 生成 N-Benzyl-N'-(6-chloro-2-methoxy-acridin-9-yl)-N-propyl-propane-1,3-diamine
  参考文献：
  名称：

  Parallel synthesis of 9-aminoacridines and their evaluation against chloroquine-resistant Plasmodium falciparum

  摘要：

  A parallel synthetic strategy to the 9-aminoacridine scaffold of the classical anti-malarial drug quinacrine (2) is presented. The method features a new route to 9-chloroacridines that utilizes triflates of salicylic acid derivatives, which are commercially available in a variety of substitution patterns. The route allows ready variation of the two diversity elements present in this class of molecules: the tricyclic aromatic heterocyclic core, and the disubstituted diamine sidechain. In this study, a library of 175 compounds was designed, although only 93 of the final products had purities acceptable for screening. Impurity was generally due to incomplete removal of 9-acridones (18), a degradation product of the 9-chloroacridine synthetic intermediates. The library was screened against two strains of Plasmodium falciparum, including a model of the drug-resistant parasite, and six novel compounds were found to have IC50 values in the low nanomolar range. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.08.017
• 作为产物：
  描述：

  N-[3-(Benzyl-propyl-amino)-propyl]-2-nitro-benzenesulfonamide 在 caesium carbonate 、 苯硫酚 作用下， 以 乙腈 为溶剂， 以74%的产率得到N'-benzyl-N'-propyl-propane-1,3-diamine
  参考文献：
  名称：

  Parallel synthesis of 9-aminoacridines and their evaluation against chloroquine-resistant Plasmodium falciparum

  摘要：

  A parallel synthetic strategy to the 9-aminoacridine scaffold of the classical anti-malarial drug quinacrine (2) is presented. The method features a new route to 9-chloroacridines that utilizes triflates of salicylic acid derivatives, which are commercially available in a variety of substitution patterns. The route allows ready variation of the two diversity elements present in this class of molecules: the tricyclic aromatic heterocyclic core, and the disubstituted diamine sidechain. In this study, a library of 175 compounds was designed, although only 93 of the final products had purities acceptable for screening. Impurity was generally due to incomplete removal of 9-acridones (18), a degradation product of the 9-chloroacridine synthetic intermediates. The library was screened against two strains of Plasmodium falciparum, including a model of the drug-resistant parasite, and six novel compounds were found to have IC50 values in the low nanomolar range. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.08.017

文献信息

• [EN] MACROMOLECULE-SUPPORTED AMINOBENZAZEPINE COMPOUNDS<br/>[FR] COMPOSÉS D'AMINOBENZAZÉPINE À SUPPORT MACROMOLÉCULAIRE
  申请人：BOLT BIOTHERAPEUTICS INC

  公开号：WO2020252254A1

  公开（公告）日：2020-12-17

  The application provides macromolecule-supported compounds of Formula I or III comprising a macromolecular support linked by conjugation to one or more aminobenzazepine derivatives. The application also provides aminobenzazepine derivative intermediate compositions of Formula II comprising a reactive functional group. Such intermediate compositions are suitable substrates for formation of the macromolecule-supported compounds through a linker or linking moiety. The application further provides compositions comprising the macromolecule-supported compounds, as well as methods of treating cancer with the macromolecule-supported compounds.

  该应用程序提供了由共轭连接到一种或多种氨基苯并二氮杂环衍生物的大分子支持的化合物，其化学式为I或III。该应用程序还提供了具有反应性功能基团的化学式II的氨基苯并二氮杂环衍生物中间体组合物。这种中间体组合物适合通过连接物或连接基团形成大分子支持的化合物。该应用程序还提供了包含大分子支持化合物的组合物，以及使用这些大分子支持化合物治疗癌症的方法。
• AMINOBENZAZEPINE COMPOUNDS, IMMUNOCONJUGATES, AND USES THEREOF
  申请人：Bolt Biotherapeutics, Inc.

  公开号：EP3983082A1

  公开（公告）日：2022-04-20
• MACROMOLECULE-SUPPORTED AMINOBENZAZEPINE COMPOUNDS
  申请人：Bolt Biotherapeutics, Inc.

  公开号：EP3983080A1

  公开（公告）日：2022-04-20
• [EN] AMINOBENZAZEPINE COMPOUNDS, IMMUNOCONJUGATES, AND USES THEREOF<br/>[FR] COMPOSÉS D'AMINOBENZAZÉPINE, IMMUNOCONJUGUÉS ET LEURS UTILISATIONS
  申请人：BOLT BIOTHERAPEUTICS INC

  公开号：WO2020252294A1

  公开（公告）日：2020-12-17

  The application relates to immunoconjugates of Formula (I) comprising an antibody linked by conjugation to one or more aminobenzazepine derivatives. The application also provides aminobenzazepine derivative intermediate compositions of Formula (II) comprising a reactive functional group. Such intermediate compositions are suitable substrates for formation of the immunoconjugates through a linker or linking moiety. The application further provides the above- mentioned immunoconjugates for use in methods of treating cancer.
• Parallel synthesis of 9-aminoacridines and their evaluation against chloroquine-resistant Plasmodium falciparum
  作者：Marc O. Anderson、John Sherrill、Peter B. Madrid、Ally P. Liou、Jennifer L. Weisman、Joseph L. DeRisi、R. Kiplin Guy

  DOI：10.1016/j.bmc.2005.08.017

  日期：2006.1

  A parallel synthetic strategy to the 9-aminoacridine scaffold of the classical anti-malarial drug quinacrine (2) is presented. The method features a new route to 9-chloroacridines that utilizes triflates of salicylic acid derivatives, which are commercially available in a variety of substitution patterns. The route allows ready variation of the two diversity elements present in this class of molecules: the tricyclic aromatic heterocyclic core, and the disubstituted diamine sidechain. In this study, a library of 175 compounds was designed, although only 93 of the final products had purities acceptable for screening. Impurity was generally due to incomplete removal of 9-acridones (18), a degradation product of the 9-chloroacridine synthetic intermediates. The library was screened against two strains of Plasmodium falciparum, including a model of the drug-resistant parasite, and six novel compounds were found to have IC50 values in the low nanomolar range. (c) 2005 Elsevier Ltd. All rights reserved.