1-[(dimethylamino)methylene]-1,3-dihydro-2H-pyrrolol[3,2-f]quinolin-2-one | 388628-24-8

• 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: 1-[(dimethylamino)methylene]-1,3-dihydro-2H-pyrrolol[3,2-f]quinolin-2-one
• 英文别名: dimethylaminomethylidene-1,3-dihydro-2H-pyrrolo[3,2-f]quinoline-2-one；1-(dimethylaminomethylidene)-3H-pyrrolo[3,2-f]quinolin-2-one
• CAS: 388628-24-8
• 化学式: C₁₄H₁₃N₃O
• 分子量: 239.277
• InChiKey: QLRZPJAGBGXTIJ-UHFFFAOYSA-N

物化性质

• 沸点：
  481.3±45.0 °C(Predicted)
• 密度：
  1.333±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  45.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  氨鲁米特 、 1-[(dimethylamino)methylene]-1,3-dihydro-2H-pyrrolol[3,2-f]quinolin-2-one 以81%的产率得到3-ethyl-3-(4-{(Z)-[(2-oxo-2,3-dihydro-1H-pyrrolo[3,2-f]quinolin-1-ylidene)methyl]amino}phenyl)-2,6-piperidinedione
  参考文献：
  名称：

  3-(anilinomethylene) oxindoles

  摘要：

  本发明一般涉及新型胺取代的噁二酮化合物和组合物。这些化合物和组合物作为药理学药剂在治疗由于一般蛋白激酶激活的信号通路的抑制或拮抗而减轻的疾病或症状方面具有实用性，特别是在涉及异常细胞增殖的病理过程中，如肿瘤生长。具体而言，本发明涉及一系列取代的噁二酮化合物，其表现出蛋白酪氨酸激酶和蛋白丝氨酸/苏氨酸激酶抑制作用，并且在通过抑制与肿瘤相关的血管生成抑制肿瘤生长方面是有用的。

  公开号：

  US06350747B1
• 作为产物：
  描述：

  1,3-dihydro-pyrrolo[3,2-f]quinoline-2-one 、 N,N-二甲基甲酰胺二叔丁基缩醛 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以70%的产率得到1-[(dimethylamino)methylene]-1,3-dihydro-2H-pyrrolol[3,2-f]quinolin-2-one
  参考文献：
  名称：

  Oxindole derivatives

  摘要：

  本文描述了一种对CDK4具有抑制作用的氧化吲哚衍生物，具体为吡咯[3,2-f]喹啉-2-酮。所述发明还包括制备这种氧化吲哚衍生物的方法，以及在治疗高增殖性疾病方面使用它们的方法。

  公开号：

  US20030195189A1

文献信息

• Oxindole-Based Inhibitors of Cyclin-Dependent Kinase 2 (CDK2):  Design, Synthesis, Enzymatic Activities, and X-ray Crystallographic Analysis
  作者：H. Neal Bramson、John Corona、Stephen T. Davis、Scott H. Dickerson、Mark Edelstein、Stephen V. Frye、Robert T. Gampe、Phil A. Harris、Anne Hassell、William D. Holmes、Robert N. Hunter、Karen E. Lackey、Brett Lovejoy、Michael J. Luzzio、Val Montana、Warren J. Rocque、David Rusnak、Lisa Shewchuk、James M. Veal、Duncan H. Walker、Lee F. Kuyper

  DOI：10.1021/jm010117d

  日期：2001.12.1

  Two closely related classes of oxindole-based compounds, 1H-indole-2,3-dione 3-phenylhydrazones and 3-(anilinomethylene)-1,3-dihydro-2H-indol-2-ones, were shown to potently inhibit cyclin-dependent kinase 2 (CDK2). The initial lead compound was prepared as a homologue of the 3-benzylidene-1,3-dihydro-2H-indol-2-one class of kinase inhibitor. Crystallographic analysis of the lead compound bound to CDK2 provided the basis for analogue design. A semiautomated method of ligand docking was used to select compounds for synthesis, and a number of compounds with low nanomolar inhibitory activity versus CDK2 were identified. Enzyme binding determinants for several analogues were evaluated by X-ray crystallography. Compounds in this series inhibited CDK2 with a potency similar to 10-fold greater than that for CDK1. Members of this class of inhibitor cause an arrest of the cell cycle and have shown potential utility in the prevention of chemotherapy-induced alopecia.
• OXINDOLE DERIVATIVES
  申请人：GLAXO GROUP LIMITED

  公开号：EP1313732B1

  公开（公告）日：2004-11-03
• US6720332B2
  申请人：——

  公开号：US6720332B2

  公开（公告）日：2004-04-13
• [EN] OXINDOLE DERIVATIVES<br/>[FR] DERIVES D'OXINDOLE
  申请人：GLAXO GROUP LTD

  公开号：WO2002020524A1

  公开（公告）日：2002-03-14

  Oxindole derivatives, specifically pyrrolo[3,2-f]quinoline-2-ones, which are useful as CDK4 inhibitors are described herein. The described invention also includes methods of making such oxindole derivatives as well as methods of using the same in the treatment of hyperproliferative diseases.
• 3-(anilinomethylene) oxindoles
  申请人：Glaxo Wellcome Inc.

  公开号：US06350747B1

  公开（公告）日：2002-02-26

  The present invention relates generally to novel amine substituted oxindole compounds and compositions. Such compounds and compositions have utility as pharmacological agents in treating diseases or conditions alleviated by the inhibition or antagonism of protein kinase activated signalling pathways in general, and in particular in the pathological processes which involve aberrant cellular proliferation, such as tumor growth. In particular, the present invention relates to a series of substituted oxindole compounds, which exhibit protein tyrosine kinase and protein serine/threonine kinase inhibition, and which are useful in inhibiting tumor growth via inhibition of tumor-related angiogenesis.

  本发明一般涉及新型胺取代的噁二酮化合物和组合物。这些化合物和组合物作为药理学药剂在治疗由于一般蛋白激酶激活的信号通路的抑制或拮抗而减轻的疾病或症状方面具有实用性，特别是在涉及异常细胞增殖的病理过程中，如肿瘤生长。具体而言，本发明涉及一系列取代的噁二酮化合物，其表现出蛋白酪氨酸激酶和蛋白丝氨酸/苏氨酸激酶抑制作用，并且在通过抑制与肿瘤相关的血管生成抑制肿瘤生长方面是有用的。