BPM19,215 | 1215290-54-2

• 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: BPM19,215
• 英文别名: N,N-bis[(8-methoxyquinolin-5-yl)methyl]-1-[4-(trifluoromethyl)phenyl]methanamine
• CAS: 1215290-54-2
• 化学式: C₃₀H₂₆F₃N₃O₂
• 分子量: 517.551
• InChiKey: RHAZKSOWSHHBEV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  38
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  47.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  JLK 1486 、 碘甲烷 在 sodium hydride 作用下， 以 乙腈 为溶剂， 反应 5.0h， 以81%的产率得到BPM19,215
  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

• 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.