4-羟基-6-甲氧基-3-苯基色烯-2-酮 | 39876-23-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 中文名称: 4-羟基-6-甲氧基-3-苯基色烯-2-酮
• 英文名称: 4-hydroxy-6-methoxy-3-phenyl-1-benzopyran-2-one
• 英文别名: 4-hydroxy-6-methoxy-3-phenylcoumarin；4-hydroxy-6-methoxy-3-phenyl-2H-chromen-2-one；4-Hydroxy-6-methoxy-3-phenyl-cumarin；6-methoxy-3-phenyl-4-hydroxy-coumarin；4-Hydroxy-6-methoxy-3-phenyl-2H-1-benzopyran-2-one；4-hydroxy-6-methoxy-3-phenylchromen-2-one
• CAS: 39876-23-8
• 化学式: C₁₆H₁₂O₄
• 分子量: 268.269
• InChiKey: FNQCMDNURWRTQE-UHFFFAOYSA-N

物化性质

• 熔点：
  205 °C
• 沸点：
  486.8±45.0 °C(Predicted)
• 密度：
  1.353±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  4-羟基-6-甲氧基-3-苯基色烯-2-酮 生成 4-acetoxy-6-methoxy-3-phenyl-coumarin
  参考文献：
  名称：

  Mentzer; Vercier, Monatshefte fur Chemie, 1957, vol. 88, p. 264,265

  摘要：

  DOI：
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 生成 4-羟基-6-甲氧基-3-苯基色烯-2-酮
  参考文献：
  名称：

  Zur Chemie des 4-Hydroxy-cumarins

  摘要：

  DOI：

  10.1007/bf00899592

文献信息

• 3-Substituted-4-aminoalkoxy-5,6-condensed ring-2-pyranones
  申请人：LIPHA, Lyonnaise Industrielle Pharmaceutique

  公开号：US04230850A1

  公开（公告）日：1980-10-28

  Novel 3-substituted-4-aminoalkoxy-5,6-condensed ring-2-pyranones are disclosed as having utility as pharmacologically active compounds, in particular vasodilatory, hypotensive, anti-ischemic and anti-tussive activity. The compounds may be 3-phenyl-4-morpholinoalkoxy-coumarins. Administration may be by the oral or parenteral route. Intermediates useful in the production of these compounds are also disclosed.

  新颖的3-取代-4-氨基烷氧基-5,6-环化-2-吡喃酮被披露为具有药理活性化合物的效用，特别是血管扩张、降压、抗缺血和镇咳活性。这些化合物可能是3-苯基-4-吗啡基烷氧基-香豆素。可以通过口服或静脉注射途径进行给药。还披露了在这些化合物生产中有用的中间体。
• 3-Phenylcoumarins as Inhibitors of HIV-1 Replication
  作者：Dionisio Olmedo、Rocío Sancho、Luis M. Bedoya、José L. López-Pérez、Esther del Olmo、Eduardo Muñoz、José Alcamí、Mahabir P. Gupta、Arturo San Feliciano

  DOI：10.3390/molecules17089245

  日期：——

  We have synthesized fourteen 3-phenylcoumarin derivatives and evaluated their anti-HIV activity. Antiviral activity was assessed on MT-2 cells infected with viral clones carrying the luciferase gene as reporter. Inhibition of HIV transcription and Tat function were tested on cells stably transfected with the HIV-LTR and Tat protein. Six compounds displayed NF-κB inhibition, four resulted Tat antagonists and three of them showed both activities. Three compounds inhibited HIV replication with IC50 values < 25 µM. The antiviral effect of the 4-hydroxycoumarin derivative 19 correlates with its specific inhibition of Tat functions, while compound 8, 3-(2-chlorophenyl)coumarin, seems to act through a mechanism unrelated to the molecular targets considered in this research.

  我们合成了十四种3-苯基香豆素衍生物，并评估了它们的抗HIV活性。抗病毒活性是在携带荧光素酶基因的病毒克隆感染的MT-2细胞上进行评估的。HIV转录和Tat功能的抑制在稳定转染了HIV-LTR和Tat蛋白的细胞上进行检测。六种化合物显示出NF-κB抑制作用，四种化合物表现出Tat拮抗作用，其中三种同时显示出这两种活性。三种化合物抑制HIV复制，其IC50值均< 25 µM。4-羟基香豆素衍生物19的抗病毒效果与其对Tat功能的特异性抑制相关，而化合物8（3-(2-氯苯基)香豆素）似乎通过一种与本研究中考虑的分子靶点无关的机制发挥作用。
• A Novel Synthesis of 4-Hydroxy-3-phenylcoumarins by Titanium(III)-Mediated Reductive C-C Bond Formation
  作者：Angelo Clerici、Ombretta Porta

  DOI：10.1055/s-1993-25808

  日期：——

  4-Hydroxy-3-phenylcoumarins (4-hydroxy-3-phenyl-2H-1-benzopyran-2-ones) were readily synthesized in two steps by the titanium(III)-mediated reaction of methyl benzoylformate and substituted salicylaldehydes followed by lactonization, under acidic conditions, of the resulting methyl 2,3-dihydroxy-3-(2-hydroxyaryl)-2-phenylpronanoates.

  4-羟基-3-苯基香豆素（4-羟基-3-苯基-2H-1-苯并呋喃-2-酮）通过钛(III)介导的反应，采用甲基苯甲酰甲酸酯和取代的水杨 aldehydes，随后在酸性条件下对得到的甲基 2,3-二羟基-3-(2-羟基芳基)-2-苯基丙酸酯进行内酯化，成功合成。
• Barton, Derek H. R.; Donnelly, Dervilla M. X.; Finet, Jean-Pierre, Journal of the Chemical Society. Perkin transactions I, 1992, p. 1365 - 1376
  作者：Barton, Derek H. R.、Donnelly, Dervilla M. X.、Finet, Jean-Pierre、Guiry, Patrick J.

  DOI：——

  日期：——
• Vercier et al., Bulletin de la Societe Chimique de France, 1950, p. 1248,1251
  作者：Vercier et al.

  DOI：——

  日期：——