Bis-(8-hydroxy-5-chinolylmethyl)-benzylamin | 97075-35-9

• 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: Bis-(8-hydroxy-5-chinolylmethyl)-benzylamin
• 英文别名: 5,5'-(benzylazanediyl)bis(methylene)diquinolin-8-ol；5,5'-(2-benzyl-2-aza-propane-1,3-diyl)-bis-quinolin-8-ol；5-({Benzyl[(8-hydroxy-5-quinolinyl)methyl]amino}methyl)-8-quinolinol；5-[[benzyl-[(8-hydroxyquinolin-5-yl)methyl]amino]methyl]quinolin-8-ol
• CAS: 97075-35-9
• 化学式: C₂₇H₂₃N₃O₂
• 分子量: 421.499
• InChiKey: LWPMUMIMHKHREW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  69.5
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  苄胺 、 5-(氯甲基)-8-羟基喹啉盐酸盐 以 乙酸乙酯 为溶剂， 以30%的产率得到Bis-(8-hydroxy-5-chinolylmethyl)-benzylamin
  参考文献：
  名称：

  Discovery of a new family of bis-8-hydroxyquinoline substituted benzylamines with pro-apoptotic activity in cancer cells: Synthesis, structure–activity relationship, and action mechanism studies

  摘要：

  Bis-8-hydroxyquinoline substituted benzylamines have been synthesized and screened for their antitumor activity on KB3 cell line model. Synthesis of this series of new analogues was accomplished using a one pot specific methodology which allows the synthesis of both bis- and mono-8-hydroxyquinoline substituted benzylamines. Among the synthesized compounds two compounds (4a and 5a), respectively, named JLK 1472 and JLK 1486, were particularly potent on KB3 cell line. Their CC50 values being, respectively, 2.6 and 1.3 nM. Screened on a panel of cell lines showing various phenotype alterations, both compounds were found inactive on some cell lines such as PC3 (prostate cell line) and SF268 (neuroblastoma cell line) while highly active on other different cell lines. Mechanistic studies reveal that these two analogues did not affect tubulin and microtubules neither they exert a proteasomal inhibition effect. In contrast 4a and 5a activate specifically caspase 3/7 and not caspase 8 and 9, suggesting that their biological target should he located upstream from caspase 3/7. Moreover their cytotoxic effect is potentiated by the pro-apoptotic effects of TRAIL. (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.03.042

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。
• Derivatives of the Aminated Hydroxyquinoline Class For Treating Cancers
  申请人：Kraus Jean-Louis

  公开号：US20100120856A1

  公开（公告）日：2010-05-13

  The invention relates to compounds of the animated hydroxyquinoline type capable of preventing the migration of metastases or tumoral cells. Such compounds are useful for treating cancers.
• US8324243B2
  申请人：——

  公开号：US8324243B2

  公开（公告）日：2012-12-04
• US8614230B2
  申请人：——

  公开号：US8614230B2

  公开（公告）日：2013-12-24