7-hydroxy-8-methyl-4-propyl-6-(1H-pyrazol-3-yl)-2H-chromen-2-one | 1010869-38-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 7-hydroxy-8-methyl-4-propyl-6-(1H-pyrazol-3-yl)-2H-chromen-2-one
• 英文别名: 7-hydroxy-8-methyl-4-propyl-6-(pyrazol-3-yl)chromen-2-one；7-hydroxy-8-methyl-4-propyl-6-(1H-pyrazol-5-yl)-2H-chromen-2-one；7-hydroxy-8-methyl-4-propyl-6-(1H-pyrazol-5-yl)chromen-2-one
• CAS: 1010869-38-1
• 化学式: C₁₆H₁₆N₂O₃
• 分子量: 284.315
• InChiKey: NHGNIWIMJNHRGT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  75.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  6-acetyl-7-hydroxy-8-methyl-4-propylchromen-2-one 在 一水合肼 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 2.0h， 生成 7-hydroxy-8-methyl-4-propyl-6-(1H-pyrazol-3-yl)-2H-chromen-2-one
  参考文献：
  名称：

  Synthesis and anticancer activity of 6-heteroarylcoumarins

  摘要：

  A series of novel 7-hydroxy-8-methyl-coumarins with indole, pyrimidine, pyrazole, pyran, tetrazolo[1,5-a]pyrimidine, pyrimido[1,2-a]benzimidazol, 2-oxo-1,2-dihydropyridine and dihydropyrazolo[3,4-b]pyridine moieties at C6 position of heterocyclic core have been synthesized. Anticancer activity screening on NCI60 cell lines allowed identification of 6-(6-fluoro-1H-indo1-2-yl)-7-hydroxy-4,8-dimethy1-2H-chromen-2-one (23) with the highest level of antimitotic activity with mean GI(50)/TGI values of 3.28/13.24 mu M and certain sensitivity profile towards the Non-Small Cell Lung Cancer cell line HOP-92 (GI(50)/TGI/LC50 values 0.95/4.17/29.9 mu M). (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.10.021

文献信息

• Modified coumarins. 30. Synthesis of 6-heteroarylcoumarins
  作者：I. V. Nagorichna、A. A. Tkachuk、M. M. Garazd、Ya. L. Garazd、V. P. Khilya

  DOI：10.1007/s10600-009-9262-9

  日期：2009.3

  Heteroarylcoumarins containing 2-indole, 3-pyrazole, and 4-pyrimidine substituents in the 6-position of the coumarin ring were synthesized.

  在香豆素环的 6 位合成了含有 2-吲哚、3-吡唑和 4-嘧啶取代基的异芳香族香豆素。
• Synthesis and anticancer activity of 6-heteroarylcoumarins
  作者：Olexandr Galayev、Yana Garazd、Myroslav Garazd、Roman Lesyk

  DOI：10.1016/j.ejmech.2015.10.021

  日期：2015.11

  A series of novel 7-hydroxy-8-methyl-coumarins with indole, pyrimidine, pyrazole, pyran, tetrazolo[1,5-a]pyrimidine, pyrimido[1,2-a]benzimidazol, 2-oxo-1,2-dihydropyridine and dihydropyrazolo[3,4-b]pyridine moieties at C6 position of heterocyclic core have been synthesized. Anticancer activity screening on NCI60 cell lines allowed identification of 6-(6-fluoro-1H-indo1-2-yl)-7-hydroxy-4,8-dimethy1-2H-chromen-2-one (23) with the highest level of antimitotic activity with mean GI(50)/TGI values of 3.28/13.24 mu M and certain sensitivity profile towards the Non-Small Cell Lung Cancer cell line HOP-92 (GI(50)/TGI/LC50 values 0.95/4.17/29.9 mu M). (C) 2015 Elsevier Masson SAS. All rights reserved.