5,7-dihydroxy-4-methyl-3-phenyl-2H-chromen-2-one | 68217-95-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 5,7-dihydroxy-4-methyl-3-phenyl-2H-chromen-2-one
• 英文别名: 5,7-dihydroxy-4-methyl-3-phenyl-coumarin；5,7-Dihydroxy-4-methyl-3-phenyl-cumarin；5,7-Dihydroxy-4-methyl-3-phenyl coumarin；5,7-dihydroxy-4-methyl-3-phenylchromen-2-one
• CAS: 68217-95-8
• 化学式: C₁₆H₁₂O₄
• 分子量: 268.269
• InChiKey: ZKOFZYMXJHXIOK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5,7-dihydroxy-4-methyl-3-phenyl-2H-chromen-2-one 、 硫酸二甲酯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 6.0h， 以89%的产率得到5,7-dimethoxy-4-methyl-3-phenylcoumarin
  参考文献：
  名称：

  A Novel and Convenient Synthesis of 3-Phenylcoumarins

  摘要：

  DOI：

  10.1055/s-1981-29633
• 作为产物：
  描述：

  sodium phenylacetate 在 氢氧化钾 作用下， 生成 5,7-dihydroxy-4-methyl-3-phenyl-2H-chromen-2-one
  参考文献：
  名称：

  344.色酮类的合成实验。第十部分香豆素和色酮的形成

  摘要：

  DOI：

  10.1039/jr9330001459

文献信息

• Neelakantan, S.; Raman, P. V.; Tinabaye, A., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1982, vol. 21, # 3, p. 256 - 257
  作者：Neelakantan, S.、Raman, P. V.、Tinabaye, A.

  DOI：——

  日期：——
• Discovery and Optimization of Novel 3-Piperazinylcoumarin Antagonist of Chemokine-like Factor 1 with Oral Antiasthma Activity in Mice
  作者：Gang Li、Dongmei Wang、Mingna Sun、Guangyan Li、Jinfeng Hu、Yun Zhang、Yuhe Yuan、Haijie Ji、Naihong Chen、Gang Liu

  DOI：10.1021/jm901652p

  日期：2010.2.25

  Chemokine-like factor 1 (CKLF1) is a novel functional cytokine that acts through receptor CC chemokine receptor 4 (CCR4). Activation of CCR4 by CKLF1 plays an important role in diseases such as asthma and multiple Sclerosis. This article describes a cell-based screening assay Using an FITC-labeled CCR4 agonist (CKLF1-C27), a CKLF1 peptide fragment. Screening of our in-stock small-molecule library identified a 3-piperazinylcoumarin analogue 1 (IC50 = 4.36 x 10(-6) M) that led to the discovery of orally active compound 41 (IC50 = 2.12 x 10(-8) M) through systematic optimization. Compound 41 blocked the calcium mobilization and chemotaxis induced by CKLF1-C27 and reduced the asthmatic pathologic changes in lung tissue of human CKLF1-transfected mice. Further studies indicated that compound 41 ameliorated pathological changes via inhibition of the NF-kappa B signal pathway.
• Jacobson; Ghosh, Journal of the Chemical Society, 1915, vol. 107, p. 1055
  作者：Jacobson、Ghosh

  DOI：——

  日期：——
• RAO, P. P.;SRIMANNARAYANA, G., SYNTHESIS, BRD, 1981, N 11, 887-888
  作者：RAO, P. P.、SRIMANNARAYANA, G.

  DOI：——

  日期：——
• AHLUWALIA V. K.; KUMAR D.; GUPTA Y.K., INDIAN. J. CHEM., 1978, B 16, NO 7, 584-586
  作者：AHLUWALIA V. K.、 KUMAR D.、 GUPTA Y.K.

  DOI：——

  日期：——