5,5'-(4-(trifluoromethoxy)benzylazanediyl)bis(methylene)diquinolin-8-ol | 1215290-40-6

• 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: 5,5'-(4-(trifluoromethoxy)benzylazanediyl)bis(methylene)diquinolin-8-ol
• 英文别名: 5-[[(8-hydroxyquinolin-5-yl)methyl-[[4-(trifluoromethoxy)phenyl]methyl]amino]methyl]quinolin-8-ol
• CAS: 1215290-40-6
• 化学式: C₂₈H₂₂F₃N₃O₃
• 分子量: 505.496
• InChiKey: QVLDEPRMLWEBHN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  37
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  78.7
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  4-(三氟甲基)苄胺 、 5-(氯甲基)-8-羟基喹啉盐酸盐 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以90%的产率得到5,5'-(4-(trifluoromethoxy)benzylazanediyl)bis(methylene)diquinolin-8-ol
  参考文献：
  名称：

  Structure–activity relationships and mechanism of action of antitumor bis 8-hydroxyquinoline substituted benzylamines

  摘要：

  A series of twenty six 8-hydroxyquinoline substituted amines, structurally related to compounds 2 and 3, were synthesized to evaluate the effects of structural changes on antitumor activity and understand their mechanism of action. The studies were performed on a wide variety of cancer cell lines within glioma and carcinoma models. The results obtained from chemical models and biological techniques such as microarrays suggest the following hypothesis that a quinone methide intermediate which does not react with DNA but which gives covalent protein thiol adducts. Micro-array analysis showed that the drugs induce the expression of a variety of stress related genes responsible for the cytotoxic and cytostatic effects in carcinoma and glioblastoma cells respectively. The described analogues could represent new promising anti-cancer candidates with specific action mechanisms, targeting accessible thiols from specific proteins and inducing potent anti-cancer effects. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.11.006

文献信息

• [EN] PPAR AGONIST COMPOSITIONS AND METHODS OF USE<br/>[FR] COMPOSITIONS AGONISTES DE PPAR ET PROCÉDÉS D'UTILISATION
  申请人：BIOPHARMED

  公开号：WO2010073235A1

  公开（公告）日：2010-07-01

  Method for treating or preventing a PPAR-responsive condition in a subject, comprising administering to the subject a PPAR agonist that comprises a 8-hydroxyquinoline-methylene-N- group in an amount effective to activate a PPAR polypeptide.

  治疗或预防主体的PPAR响应性疾病的方法，包括向主体给予一种PPAR激动剂，该激动剂包括一种8-羟基喹啉-亚甲基-N-基团，其有效剂量能够激活PPAR多肽。
• PPAR AGONIST COMPOSITIONS AND METHODS OF USE
  申请人：Kraus Jean-Louis

  公开号：US20110251238A1

  公开（公告）日：2011-10-13

  Method for treating or preventing a PPAR-responsive condition in a subject, comprising administering to the subject a PPAR agonist that comprises a 8-hydroxyquinoline-methylene-N- group in an amount effective to activate a PPAR polypeptide.

  治疗或预防受体PPAR反应性疾病的方法，包括向受体施用含有8-羟基喹啉-亚甲基-N-基团的PPAR激动剂，以有效激活PPAR多肽。
• Structure–activity relationships and mechanism of action of antitumor bis 8-hydroxyquinoline substituted benzylamines
  作者：Sébastien Madonna、Christophe Béclin、Younes Laras、Vincent Moret、Aline Marcowycz、Delphine Lamoral-Theys、Jacques Dubois、Magali Barthelemy-Requin、Gaëlle Lenglet、Sabine Depauw、Thierry Cresteil、Geneviève Aubert、Valérie Monnier、Robert Kiss、Marie-Hélène David-Cordonnier、Jean-Louis Kraus

  DOI：10.1016/j.ejmech.2009.11.006

  日期：2010.2

  A series of twenty six 8-hydroxyquinoline substituted amines, structurally related to compounds 2 and 3, were synthesized to evaluate the effects of structural changes on antitumor activity and understand their mechanism of action. The studies were performed on a wide variety of cancer cell lines within glioma and carcinoma models. The results obtained from chemical models and biological techniques such as microarrays suggest the following hypothesis that a quinone methide intermediate which does not react with DNA but which gives covalent protein thiol adducts. Micro-array analysis showed that the drugs induce the expression of a variety of stress related genes responsible for the cytotoxic and cytostatic effects in carcinoma and glioblastoma cells respectively. The described analogues could represent new promising anti-cancer candidates with specific action mechanisms, targeting accessible thiols from specific proteins and inducing potent anti-cancer effects. (C) 2009 Elsevier Masson SAS. All rights reserved.