2-[2-Oxo-1,2-dihydro-indol-(3Z)-ylidene]-1,2-dihydropyrrolo[2,3-b]pyridin-3-one | 1234205-50-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并吡啶类
• 英文名称: 2-[2-Oxo-1,2-dihydro-indol-(3Z)-ylidene]-1,2-dihydropyrrolo[2,3-b]pyridin-3-one
• 英文别名: azaindirubin；(2Z)-2-(2-oxo-1H-indol-3-ylidene)-1H-pyrrolo[2,3-b]pyridin-3-one
• CAS: 1234205-50-5
• 化学式: C₁₅H₉N₃O₂
• 分子量: 263.255
• InChiKey: QJYJTTJDFSTQJN-QXMHVHEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.05
• 重原子数：
  20.0
• 可旋转键数：
  0.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  71.09
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  靛红 、 1-phenylsulfonyl-1H-pyrrolo<2,3-b>pyridine-3(2H)-one 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 2-[2-Oxo-1,2-dihydro-indol-(3Z)-ylidene]-1,2-dihydropyrrolo[2,3-b]pyridin-3-one
  参考文献：
  名称：

  Synthesis and CDK2 kinase inhibitory activity of 7/7′-azaindirubin derivatives

  摘要：

  A series of novel 7'-azaindirubin (1a-g) and 7-azaindirubin (2a, 2c, 2e and 2f) derivatives were designed and synthesized. Their structures were characterized by (1)H NMR and MS spectroscopy as well as by elemental analysis. Their inhibitory properties against CDK2/cylinA were evaluated in vitro. In contrast to indirubin, some of the described azaindirubins emerged as potent inhibitors of CDK2/cylinA and compound 2b had more potent activity. Biological tests also showed that nitrogen atom at 7-position of azaindirubin was more beneficial to enhance the kinase inhibitory activity. (C) 2009 Qi Zheng Yao. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2009.11.029

文献信息

• 3-Hydroxypyrrolo[2,3-b]pyridine and related compounds – indoxyl analogues with fused electron deficient rings
  作者：Alexander P. Gaywood、Hamish McNab

  DOI：10.1039/c0ob00076k

  日期：——

  2-position and reacts with methoxymethylene Meldrum's acid at the 1-position. FVP of the corresponding acetyltetrazolo[1,5-a]quinoline 19 was much more complex, with 2-(cyanophenyl)acetonitrile 30 (rather than a heteroindoxyl) the major product at 750 °C. FVP of 3-acetyl-4-azidoquinoline 24 at 400 °C gave 3-methylisoxazolo[4,3-c]quinoline 33, but rearrangement to the heteroindoxyl was not observed at

  闪蒸真空热解（FVP） 4-乙酰基四唑并[1,5- a ]吡啶 5在400°C时可提供3-甲基异恶唑并[3,4- b ]吡啶 通过X射线晶体学证实其结构的6。在较高的热解温度下，不稳定异吲哚基 获得8，它以酮形式存在（1,2-二氢吡咯并[2,3- b ]吡啶-3-）8K英寸CDCl 3 溶液和烯醇互变异构体（3-羟基吡咯并[2,3- b ]吡啶）8E在二甲基亚砜。这异吲哚基 8氧化二聚为异靛蓝9，在2位发生缩合反应并与甲氧基亚甲基Meldrum的酸位于1位。FVP对应乙酰四唑并[1,5- a ]喹啉 19要复杂得多，2-（氰基苯基）乙腈 主要产品在750°C下达到30（而不是杂吲哚基）。的FVP3-乙酰基-4-叠氮喹啉 在400°C下243-甲基异唑并[4,3- c ]喹啉 如图33所示，但在较高温度下未观察到重配成杂吲哚基。