4-amino-N-(5-aminopyridin-2-yl)benzamide

• 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-amino-N-(5-aminopyridin-2-yl)benzamide
• 化学式: C₁₂H₁₂N₄O
• 分子量: 228.253
• InChiKey: ASEPAAUQEHLJFI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  94
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-amino-N-(5-aminopyridin-2-yl)benzamide 、 2-thioxo-imidazolidine-1,3-dicarboxylic acid di-tert-butyl ester 在 三乙胺 、 mercury dichloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以89%的产率得到di-tert-butyl 2-((6-(4-((1,3-bis(tert-butoxycarbonyl)imidazolidin-2-ylidene)amino)benzamido)pyridin-3-yl)imino)imidazolidine-1,3-dicarboxylate
  参考文献：
  名称：

  Lowering the p K a of a bisimidazoline lead with halogen atoms results in improved activity and selectivity against Trypanosoma brucei in vitro

  摘要：

  Diphenyl-based bis(2-iminoimidazolidines) are promising antiprotozoal agents that are curative in mouse models of stage 1 tiypanosomiasis but devoid of activity in the late-stage disease, possibly due to poor brain penetration caused by their dicationic nature. We present here a strategy consisting in reducing the pK(a) of the basic 2-iminoimidazolidine groups though the introduction of chlorophenyl, fluorophenyl and pyridyl ring in the structure of the trypanocidal lead 4-(imidazolidin-2-ylideneamino)-N-(4-(imidazolidin-2-ylideneamino)phenyl)benzamide (1). The new compounds showed reduced pK(a) values (in the range 1-3 pK(a) units) for the imidazolidine group linked to the substituted phenyl ring. In vitro activities (EC50) against wild type and resistant strains of T. b. brucei (s427 and B48, respectively) were in the submicromolar range with four compounds being more active and selective than 1 (SI > 340). In particular, the two most potent compounds (3b and 5a) acted approximately 6-times faster than 1 to kill trypanosomes in vitro. No cross-resistance with the diamidine and melaminophenyl class of trypanocides was observed indicating that these compounds represent interesting leads for further in vivo studies. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.07.013
• 作为产物：
  描述：

  4-nitro-N-(5-nitropyridin-2-yl)benzamide 在 palladium on activated charcoal 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 以83 %的产率得到4-amino-N-(5-aminopyridin-2-yl)benzamide
  参考文献：
  名称：

  Synthesis and Biophysical and Biological Studies of N-Phenylbenzamide Derivatives Targeting Kinetoplastid Parasites

  摘要：

  DOI：

  10.1021/acs.jmedchem.3c00697

文献信息

• LIQUID CRYSTAL ALIGNMENT AGENT COMPOSITION, METHOD OF PREPARING LIQUID CRYSTAL ALIGNMENT FILM, AND LIQUID CRYSTAL ALIGNMENT FILM, AND LIQUID CRYSTAL DISPLAY USING THE SAME
  申请人：LG CHEM, LTD.

  公开号：US20210139782A1

  公开（公告）日：2021-05-13

  The present invention relates to a liquid crystal alignment agent composition including a copolymer for liquid crystal alignment agent containing two types of repeating units classified according to the types of diamine-derived functional groups, and a crosslinker compound in which the protecting group having a specific structure was introduced, a method for preparing a liquid crystal alignment film using the same, and a liquid crystal alignment film and a liquid crystal display device using the same.
• [EN] LIQUID CRYSTAL ALIGNMENT COMPOSITION, METHOD OF PREPARING LIQUID CRYSTAL ALIGNMENT FILM USING SAME, AND LIQUID CRYSTAL ALIGNMENT FILM AND LIQUID CRYSTAL DISPLAY USING SAME<br/>[FR] COMPOSITION D'ALIGNEMENT DE CRISTAUX LIQUIDES, PROCÉDÉ DE PRÉPARATION D'UN FILM D'ALIGNEMENT DE CRISTAUX LIQUIDES L'UTILISANT, ET FILM D'ALIGNEMENT DE CRISTAUX LIQUIDES ET AFFICHAGE À CRISTAUX LIQUIDES L'UTILISANT<br/>[KO] 액정 배향제 조성물, 이를 이용한 액정 배향막의 제조 방법, 이를 이용한 액정 배향막 및 액정표시소자
  申请人：LG CHEMICAL LTD

  公开号：WO2020149574A1

  公开（公告）日：2020-07-23

  본 발명은 디아민 유래 작용기 종류에 따라 구분되는 2종의 반복단위를 포함하는 액정 배향제용 공중합체 및 특정 구조의 보호기가 도입된 가교제 화합물을 포함하는 액정 배향제 조성물, 이를 이용한 액정 배향막의 제조 방법, 이를 이용한 액정 배향막 및 액정 표시소자에 관한 것이다.
• Lowering the p K a of a bisimidazoline lead with halogen atoms results in improved activity and selectivity against Trypanosoma brucei in vitro
  作者：Carlos H. Ríos Martínez、J. Jonathan Nué Martínez、Godwin U. Ebiloma、Harry P. de Koning、Ibon Alkorta、Christophe Dardonville

  DOI：10.1016/j.ejmech.2015.07.013

  日期：2015.8

  Diphenyl-based bis(2-iminoimidazolidines) are promising antiprotozoal agents that are curative in mouse models of stage 1 tiypanosomiasis but devoid of activity in the late-stage disease, possibly due to poor brain penetration caused by their dicationic nature. We present here a strategy consisting in reducing the pK(a) of the basic 2-iminoimidazolidine groups though the introduction of chlorophenyl, fluorophenyl and pyridyl ring in the structure of the trypanocidal lead 4-(imidazolidin-2-ylideneamino)-N-(4-(imidazolidin-2-ylideneamino)phenyl)benzamide (1). The new compounds showed reduced pK(a) values (in the range 1-3 pK(a) units) for the imidazolidine group linked to the substituted phenyl ring. In vitro activities (EC50) against wild type and resistant strains of T. b. brucei (s427 and B48, respectively) were in the submicromolar range with four compounds being more active and selective than 1 (SI > 340). In particular, the two most potent compounds (3b and 5a) acted approximately 6-times faster than 1 to kill trypanosomes in vitro. No cross-resistance with the diamidine and melaminophenyl class of trypanocides was observed indicating that these compounds represent interesting leads for further in vivo studies. (C) 2015 Elsevier Masson SAS. All rights reserved.
• Synthesis and Biophysical and Biological Studies of <i>N</i>-Phenylbenzamide Derivatives Targeting Kinetoplastid Parasites
  作者：J. Jonathan Nué-Martinez、David Cisneros、María del Valle Moreno-Blázquez、Cristina Fonseca-Berzal、José Ignacio Manzano、Damien Kraeutler、Marzuq A. Ungogo、Maha A. Aloraini、Hamza A. A. Elati、Alexandra Ibáñez-Escribano、Laura Lagartera、Tomás Herraiz、Francisco Gamarro、Harry P. de Koning、Alicia Gómez-Barrio、Christophe Dardonville

  DOI：10.1021/acs.jmedchem.3c00697

  日期：2023.10.12