4-(acridin-9-ylamino)-3-nitrobenzoic acid | 1211776-36-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 4-(acridin-9-ylamino)-3-nitrobenzoic acid
• CAS: 1211776-36-1
• 化学式: C₂₀H₁₃N₃O₄
• 分子量: 359.341
• InChiKey: LJOSVXQWJBHKKI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  108
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-(acridin-9-ylamino)-3-nitrobenzoic acid 、 C₆H₁₃N₂O₂Pol 在 N-甲基吗啉 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 1,2-乙二硫醇 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 、 水 为溶剂， 反应 0.67h， 生成 2,6-bis(4-(acridin-9-ylamino)-3-nitrobenzamido)hexanoic acid
  参考文献：
  名称：

  A fast entry to the novel medicinally-important 9-anilinoacridine peptidyls by solid phase organic synthesis (SPOS)

  摘要：

  A new approach to the synthesis of novel medicinally-important mono- and bis-9-anilinoacridine (9-AnA) peptidyl derivatives is described. The method generates efficiently 9-AnAs with variable spacer lengths and charged, polar or hydrophobic residues at desired positions, which can increase binding affinity, conformational stability, intracellular transport and/or biological activity. The synthetic routes reported in this work are both general and applicable, and significantly expand the scope of potential 9-aminoacridine (9-AA) anticancer candidates. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.05.023
• 作为产物：
  描述：

  C₂₀H₁₂N₃O₄Pol 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 4-(acridin-9-ylamino)-3-nitrobenzoic acid
  参考文献：
  名称：

  [EN] 9-AMINOACRIDINE DERIVATIVES, THEIR PREPARATION AND USES
  [FR] DÉRIVÉS DE 9-AMINOACRIDINE, LEUR PRÉPARATION ET LEURS UTILISATIONS

  摘要：

  含有取代基的9-氨基吖啶和含有电子吸引基团（EWG）或电子供给基团（EDG）的双吖啶衍生物，包括氨基酸残基，以及它们的合成的一锅法被披露。这些衍生物是潜在的癌症治疗候选物。

  公开号：

  WO2011051950A1

文献信息

• “Switch off/switch on” regulation of drug cytotoxicity by conjugation to a cell targeting peptide
  作者：Yossi Gilad、Michael A. Firer、Alex Rozovsky、Elena Ragozin、Boris Redko、Amnon Albeck、Gary Gellerman

  DOI：10.1016/j.ejmech.2014.07.073

  日期：2014.10

  Bi-nuclear amino acid platforms loaded with various drugs for conjugation to a peptide carrier were synthesized using simple and convenient orthogonally protective solid-phase organic synthesis (SPOS). Each arm of the platform carries a different anticancer agent linked through the same or different functional group, providing discrete chemo- and bio-release profiles for each drug, and also enabling

  使用简单方便的正交保护固相有机合成（SPOS）合成了负载有多种药物的双核氨基酸平台，这些平台可与肽载体偶联。该平台的每个臂均带有通过相同或不同功能基团连接的不同抗癌剂，从而为每种药物提供了离散的化学释放和生物释放特性，并且还可以通过与药物的缀合来“关闭/开启”调节药物的细胞毒性。平台和细胞靶向肽。这种方法的多功能性使得能够高效生产载药平台，并确定有利的药物组合/连接方式，以便随后缀合至靶向癌细胞治疗的载体部分。
• 9-AMINOACRIDINE DERIVATIVES, THEIR PREPARATION AND USES
  申请人：Gellerman Gary

  公开号：US20120220537A1

  公开（公告）日：2012-08-30

  N-substituted 9-aminoacridine and bis-acridino derivatives containing electron-withdrawing groups (EWG) or electron-donating groups (EDG), including amino acid residues, and one-pot methods for their synthesis are disclosed. The derivatives are potential candidates for cancer treatment.

  本发明公开了含有电子吸引基团（EWG）或电子供给基团（EDG），包括氨基酸残基的N-取代9-氨基蒽和双蒽衍生物及其一锅法合成方法。这些衍生物是癌症治疗的潜在候选物。
• One-pot derivatization of medicinally important 9-aminoacridines by reductive amination and SNAr reaction
  作者：Gary Gellerman、Vladimir Gaisin、Tamara Brider

  DOI：10.1016/j.tetlet.2009.12.020

  日期：2010.2

  A new highly efficient one-pot derivatization of medicinally important 9-aminoacridines (9-AA) at the amine position is described. Simple reductive amination and SNAr reaction using easily accessible starting materials give a fast entry to novel 9-AA derivatives for biological screening. (c) 2009 Elsevier Ltd. All rights reserved.
• [EN] 9-AMINOACRIDINE DERIVATIVES, THEIR PREPARATION AND USES<br/>[FR] DÉRIVÉS DE 9-AMINOACRIDINE, LEUR PRÉPARATION ET LEURS UTILISATIONS
  申请人：UNIV ARIEL RES & DEV CO LTD

  公开号：WO2011051950A1

  公开（公告）日：2011-05-05

  N-substituted 9-aminoacridine and bis-acridino derivatives containing electron- withdrawing groups (EWG) or electron-donating groups (EDG), including amino acid residues, and one-pot methods for their synthesis are disclosed. The derivatives are potential candidates for cancer treatment.

  含有取代基的9-氨基吖啶和含有电子吸引基团（EWG）或电子供给基团（EDG）的双吖啶衍生物，包括氨基酸残基，以及它们的合成的一锅法被披露。这些衍生物是潜在的癌症治疗候选物。
• A fast entry to the novel medicinally-important 9-anilinoacridine peptidyls by solid phase organic synthesis (SPOS)
  作者：Tamara Brider、Yossi Gilad、Gary Gellerman

  DOI：10.1016/j.tetlet.2011.05.023

  日期：2011.7

  A new approach to the synthesis of novel medicinally-important mono- and bis-9-anilinoacridine (9-AnA) peptidyl derivatives is described. The method generates efficiently 9-AnAs with variable spacer lengths and charged, polar or hydrophobic residues at desired positions, which can increase binding affinity, conformational stability, intracellular transport and/or biological activity. The synthetic routes reported in this work are both general and applicable, and significantly expand the scope of potential 9-aminoacridine (9-AA) anticancer candidates. (C) 2011 Elsevier Ltd. All rights reserved.