3-formylimidazo[1,2-a]pyridine-6-carbonitrile | 1019019-92-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 英文名称: 3-formylimidazo[1,2-a]pyridine-6-carbonitrile
• CAS: 1019019-92-1
• 化学式: C₉H₅N₃O
• mdl: MFCD09994345
• 分子量: 171.158
• InChiKey: YSLAWDMCNJBCGA-UHFFFAOYSA-N

物化性质

• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  58.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-formylimidazo[1,2-a]pyridine-6-carbonitrile 在 sodium hydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  Design, synthesis and biological evaluation of acylhydrazone derivatives as PI3K inhibitors

  摘要：

  Since the PI3K signaling pathway is the most commonly activated in human cancers, inhibition of PI3K K is a promising approach to cancer therapy. In this study, a series of 2-methyl-5-nitrobenzeneacylhydrazones were designed and synthesized. All the new derivatives were tested by p110 alpha enzymatic and Rh30 cellular assays. Further enzyme selectivity profiling proved that 6e and 7 were potential selective P13K inhibitors. (C) 2014 Ling-Hua Meng and Wen-Hu Duan. Published by Elsevier B.V. on behalf of Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. All rights reserved.

  DOI：

  10.1016/j.cclet.2014.10.016
• 作为产物：
  描述：

  2-氨基-5-氰基吡啶 、 2-溴丙二醛 以 乙醇 、 水 为溶剂， 反应 0.17h， 以73%的产率得到3-formylimidazo[1,2-a]pyridine-6-carbonitrile
  参考文献：
  名称：

  微波辅助合成3-甲酰基取代的咪唑并[1,2- a ]吡啶

  摘要：

  一种高效，无金属的3-甲酰基咪唑合成方法[1,2- 据报道有]吡啶。该方法利用可商购的基材，并且具有广泛的基材范围。分离了中间体烯胺，并提出了合理的反应机理。

  DOI：

  10.1016/j.tetlet.2019.151244

文献信息

• Functionalization of the imidazo[1,2-<i>a</i>]pyridine ring in α-phosphonoacrylates and α-phosphonopropionates via microwave-assisted Mizoroki–Heck reaction
  作者：Damian Kusy、Agata Wojciechowska、Joanna Małolepsza、Katarzyna M Błażewska

  DOI：10.3762/bjoc.16.3

  日期：——

  A series of new phosphonocarboxylates containing an imidazo[1,2-a]pyridine ring has been synthesized via the microwave-assisted Mizoroki-Heck reaction. The efficient modification of the imidazo[1,2-a]pyridine ring has been achieved as late-stage functionalization, enabling and accelerating the generation of a library of compounds from a common precursor.

  通过微波辅助的Mizoroki-Heck反应合成了一系列含有咪唑并[1,2-a]吡啶环的新膦酰基羧酸酯。咪唑并[1,2-a]吡啶环的有效修饰已作为后期功能化而实现，从而能够并加速从常见前体生成化合物库。
• Synthesis and biological evaluation of sulfonylhydrazone-substituted imidazo[1,2-a]pyridines as novel PI3 kinase p110α inhibitors
  作者：Masahiko Hayakawa、Ken-ichi Kawaguchi、Hiroyuki Kaizawa、Tomonobu Koizumi、Takahide Ohishi、Mayumi Yamano、Minoru Okada、Mitsuaki Ohta、Shin-ichi Tsukamoto、Florence I. Raynaud

  DOI：10.1016/j.bmc.2007.05.070

  日期：2007.9.1

  We have previously reported the imidazo[1,2-a]pyridine derivative 4 as a novel p110 alpha inhibitor; however, although 4 is a potent inhibitor of p110 alpha enzymatic activity and tumor cell proliferation in vitro, it is unstable in solution and ineffective in vivo. To increase stability the pyrazole of 4 was replaced with a hydrazone and a moderately potent p110 alpha inhibitor 7a was obtained. Subsequent optimization of 7a afforded exceptionally potent p110 alpha inhibitors, including 8c and 8h, with IC(50) values of 0.30 nM and 0.26 nM, respectively; to the best of our knowledge, these compounds are the most potent PI3K p110 alpha inhibitors reported to date. Compound 8c was also stable in solution and exhibited significant anti-tumor effectiveness in vivo. (c) 2007 Elsevier Ltd. All rights reserved.