3-formylphenyl-3,4-dihydropyrrolo[4,3,2-de]isoquinolin-5-(1H)-one | 478943-31-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 3-formylphenyl-3,4-dihydropyrrolo[4,3,2-de]isoquinolin-5-(1H)-one
• 英文别名: 3-(7-Oxo-2,6-diazatricyclo[6.3.1.04,12]dodeca-1(11),3,8(12),9-tetraen-3-yl)benzaldehyde
• CAS: 478943-31-6
• 化学式: C₁₇H₁₂N₂O₂
• 分子量: 276.294
• InChiKey: IXFCWMTUGZTKIR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  62
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  二甲胺 、 3-formylphenyl-3,4-dihydropyrrolo[4,3,2-de]isoquinolin-5-(1H)-one 在 盐酸 、 sodium cyanoborohydride 、 zinc(II) chloride 作用下， 以 甲醇 为溶剂， 反应 72.0h， 以42%的产率得到2-(3-Dimethylaminomethyl-phenyl)-3,4-dihydro-1H-pyrrolo[4,3,2-de]isoquinolin-5-one
  参考文献：
  名称：

  Novel Tricyclic Poly(ADP-ribose) Polymerase-1 Inhibitors with Potent Anticancer Chemopotentiating Activity:  Design, Synthesis, and X-ray Cocrystal Structure

  摘要：

  A series of novel compounds have been designed that are potent inhibitors of poly(ADP-ribose) polymerase-1 (PARP-1), and the activity and physical properties have been characterized. The new structural classes, 3,4,5,6-tetrahydro-1H-azepino[5,4,3-cd]indol-6-ones and 3,4-dihydropyrrolo[4,3,2-de]isoquinolin-5-(1H)-ones, have conformationally locked benzamide cores that specifically interact with the PARP-1 protein. The compounds have been evaluated with in vitro cellular assays that measure the ability of the PARP-1 inhibitors to enhance the effect of cytotoxic agents against cancer cell lines.

  DOI：

  10.1021/jm020259n
• 作为产物：
  描述：

  1,3-二氢吡咯并[4,3,2-de]异喹啉-5(4H)-酮 在 四(三苯基膦)钯 、 sodium carbonate 、 pyridinium hydrobromide perbromide 、 lithium chloride 作用下， 以 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 48.5h， 生成 3-formylphenyl-3,4-dihydropyrrolo[4,3,2-de]isoquinolin-5-(1H)-one
  参考文献：
  名称：

  Novel Tricyclic Poly(ADP-ribose) Polymerase-1 Inhibitors with Potent Anticancer Chemopotentiating Activity:  Design, Synthesis, and X-ray Cocrystal Structure

  摘要：

  A series of novel compounds have been designed that are potent inhibitors of poly(ADP-ribose) polymerase-1 (PARP-1), and the activity and physical properties have been characterized. The new structural classes, 3,4,5,6-tetrahydro-1H-azepino[5,4,3-cd]indol-6-ones and 3,4-dihydropyrrolo[4,3,2-de]isoquinolin-5-(1H)-ones, have conformationally locked benzamide cores that specifically interact with the PARP-1 protein. The compounds have been evaluated with in vitro cellular assays that measure the ability of the PARP-1 inhibitors to enhance the effect of cytotoxic agents against cancer cell lines.

  DOI：

  10.1021/jm020259n

文献信息

• Novel Tricyclic Poly(ADP-ribose) Polymerase-1 Inhibitors with Potent Anticancer Chemopotentiating Activity:  Design, Synthesis, and X-ray Cocrystal Structure
  作者：Stacie S. Canan Koch、Lars H. Thoresen、Jayashree G. Tikhe、Karen A. Maegley、Robert J. Almassy、Jianke Li、Xiao-Hong Yu、Scott E. Zook、Robert A. Kumpf、Cathy Zhang、Theodore J. Boritzki、Rena N. Mansour、Kanyin E. Zhang、Anne Ekker、Chris R. Calabrese、Nicola J. Curtin、Suzanne Kyle、Huw D. Thomas、Lan-Zhen Wang、A. Hilary Calvert、Bernard T. Golding、Roger J. Griffin、David R. Newell、Stephen E. Webber、Zdenek Hostomsky

  DOI：10.1021/jm020259n

  日期：2002.11.1

  A series of novel compounds have been designed that are potent inhibitors of poly(ADP-ribose) polymerase-1 (PARP-1), and the activity and physical properties have been characterized. The new structural classes, 3,4,5,6-tetrahydro-1H-azepino[5,4,3-cd]indol-6-ones and 3,4-dihydropyrrolo[4,3,2-de]isoquinolin-5-(1H)-ones, have conformationally locked benzamide cores that specifically interact with the PARP-1 protein. The compounds have been evaluated with in vitro cellular assays that measure the ability of the PARP-1 inhibitors to enhance the effect of cytotoxic agents against cancer cell lines.