11-Hydroxy-6-[(4-methoxyphenyl)methyl]-11-methylindeno[1,2-c]isoquinolin-5-one | 1018679-06-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 11-Hydroxy-6-[(4-methoxyphenyl)methyl]-11-methylindeno[1,2-c]isoquinolin-5-one
• CAS: 1018679-06-5
• 化学式: C₂₅H₂₁NO₃
• 分子量: 383.447
• InChiKey: AOEMGULMSZSEKL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  6-(4-methoxybenzyl)-6H-indeno[1,2-c]isoquinoline-5,11-dione 、 甲基溴化镁 以 四氢呋喃 、 二丁醚 为溶剂， 反应 12.0h， 以79%的产率得到11-Hydroxy-6-[(4-methoxyphenyl)methyl]-11-methylindeno[1,2-c]isoquinolin-5-one
  参考文献：
  名称：

  Indeno[1,2-c]isoquinolines as enhancing agents on all-trans retinoic acid-mediated differentiation of human myeloid leukemia cells

  摘要：

  Induction of differentiation is a new and promising approach to cancer therapy, well illustrated by the treatment of acute myeloid leukemia with all-trans retinoic acid (ATRA). Using combination of ATRA and chemotherapy, adverse effects such as retinoic acid syndrome have decreased, and long-term survival has improved. In this study, we demonstrated that the indeno[1,2-c]isoquinolines markedly enhanced differentiation of human myeloid leukemia HL-60 and NB4 cells when simultaneously combined with a low dose of ATRA. Of the tested compounds, 6-(4-methoxybenzyl)-2,11-dimethyl-6H, 11H-indeno[1,2-c]isoquinolin-5-one (IIQ-16), an indeno[1,2-c]isoquinoline derivative, showed the highest differentiation-enhancing activity via a pathway involved with protein kinase C, extracellular signal-regulated kinase, and e-Jun N-terminal kinase. The ability to enhance the differentiation potential of ATRA by IIQ-16 may improve outcomes in the therapy of acute promyelocytic leukemia. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.10.086

文献信息

• Indeno[1,2-c]isoquinolines as enhancing agents on all-trans retinoic acid-mediated differentiation of human myeloid leukemia cells
  作者：Seung Hyun Kim、Sang Mi Oh、Ju Han Song、Daeho Cho、Quynh Manh Le、Suh–Hee Lee、Won-Jea Cho、Tae Sung Kim

  DOI：10.1016/j.bmc.2007.10.086

  日期：2008.2.1

  Induction of differentiation is a new and promising approach to cancer therapy, well illustrated by the treatment of acute myeloid leukemia with all-trans retinoic acid (ATRA). Using combination of ATRA and chemotherapy, adverse effects such as retinoic acid syndrome have decreased, and long-term survival has improved. In this study, we demonstrated that the indeno[1,2-c]isoquinolines markedly enhanced differentiation of human myeloid leukemia HL-60 and NB4 cells when simultaneously combined with a low dose of ATRA. Of the tested compounds, 6-(4-methoxybenzyl)-2,11-dimethyl-6H, 11H-indeno[1,2-c]isoquinolin-5-one (IIQ-16), an indeno[1,2-c]isoquinoline derivative, showed the highest differentiation-enhancing activity via a pathway involved with protein kinase C, extracellular signal-regulated kinase, and e-Jun N-terminal kinase. The ability to enhance the differentiation potential of ATRA by IIQ-16 may improve outcomes in the therapy of acute promyelocytic leukemia. (c) 2007 Elsevier Ltd. All rights reserved.