3-ethyl-4-hydroxy-7-methoxy-2H-chromen-2-one | 55939-27-0

• 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: 3-ethyl-4-hydroxy-7-methoxy-2H-chromen-2-one
• 英文别名: 3-Aethyl-4-hydroxy-7-methoxy-coumarin；3-ethyl-4-hydroxy-7-methoxy-chromen-2-one；3-ethyl-4-hydroxy-7-methoxy-coumarin；3-Aethyl-4-hydroxy-7-methoxy-cumarin；3-Ethyl-4-hydroxy-7-methoxychromen-2-one；3-ethyl-4-hydroxy-7-methoxychromen-2-one
• CAS: 55939-27-0
• 化学式: C₁₂H₁₂O₄
• 分子量: 220.225
• InChiKey: XDZIPNSSXOVRNL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-ethyl-4-hydroxy-7-methoxy-2H-chromen-2-one 生成 3-ethyl-4,7-dimethoxy-chromen-2-one
  参考文献：
  名称：

  Garden et al., Journal of the Chemical Society, 1956, p. 3315,3317

  摘要：

  DOI：
• 作为产物：
  描述：

  3-acetyl-4-hydroxy-7-methoxycoumarin 在 sodium cyanoborohydride 、 溶剂黄146 作用下， 反应 0.5h， 以78%的产率得到3-ethyl-4-hydroxy-7-methoxy-2H-chromen-2-one
  参考文献：
  名称：

  Discovery of coumarin derivatives as potent and selective cyclin-dependent kinase 9 (CDK9) inhibitors with high antitumour activity

  摘要：

  Specific inhibition of CDK9 is considered a promising strategy for developing effective anticancer therapeutics. However, most of the reported CDK9 inhibitors are still at an early stage of development and lack selectivity against other CDKs. Herein, we discovered coumarin derivative 30i as a potent CDK9 inhibitor with high selectivity (8300-fold over CDK7). Binding mode analysis illustrated that the substituent coumarin moiety is a critical group for CDK9 selectivity by occupying a flexible hinge/alpha D region, which is sterically hindered in other CDKs. Compound 30i showed excellent cellular antiproliferative activity, moderate pharmacokinetic property and low hERG inhibition. Moreover, 30i significantly induced tumour growth inhibition in a dose-dependent manner without causing an obvious loss of body weight in an MV4-11 xenograft mice model. Altogether, these results suggest that 30i may serve as a potential acute myeloid leukaemia (AML) therapeutics by selectively targeting CDK9. (C) 2020 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2020.112424

文献信息

• XXXVI.—Syntheses of antiseptic derivatives of indan-1 : 3-dione. Part I. Interaction of malonyl chloride and of alkylmalonyl chlorides with the methyl ethers of resorcinol and β-naphthol
  作者：Raphael Black、Herbert Shaw、Thomas Kennedy Walker

  DOI：10.1039/jr9310000272

  日期：——