7-(hydroxymethyl)-4-phenylnaphtho<2,3-c>furan-1(3H)-one | 145127-72-6

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 芳基萘木脂素
• 英文名称: 7-(hydroxymethyl)-4-phenylnaphtho<2,3-c>furan-1(3H)-one
• 英文别名: 6-(hydroxymethyl)-9-phenyl-1H-benzo[f][2]benzofuran-3-one
• CAS: 145127-72-6
• 化学式: C₁₉H₁₄O₃
• 分子量: 290.318
• InChiKey: CGFZVYWBGNYGNE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7-(hydroxymethyl)-4-phenylnaphtho<2,3-c>furan-1(3H)-one 在 咪唑 、 四溴化碳 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以76%的产率得到7-(bromomethyl)-4-phenylnaphtho<2,3-c>furan-1(3H)-one
  参考文献：
  名称：

  Naphthalenic Lignan Lactones as Selective, Nonredox 5-Lipoxygenase Inhibitors. Synthesis and Biological Activity of (Methoxyalkyl)thiazole and Methoxytetrahydropyran Hybrids

  摘要：

  Combinations of structural elements found in (methoxyalkyl)thiazole 1a and methoxytetrahydropyran 2a with a naphthalenic lignan lactone produce the potent 5-lipoxygenase (5-LO) inhibitors 3 and 4. While the nature of link Y-Z has a major effect on the in vitro activity of compounds 1 and 2, inhibitors 3 and 4 retain their potencies with either an oxymethylene (Y = O, Z = CH2) or a methyleneoxy (Y = CH2, Z = O) link. Compound 4b inhibits the oxidation of arachidonic acid to 5-hydroperoxyeicosatetraenoic acid by 5-LO (IC50 = 14 nM) and the formation of leukotriene Bq in human polymorphonuclear leukocytes (IC50 = 1.5 nM) as well as in human whole blood (IC50 = 50 nM). Compound 4b is a selective 5-LO inhibitor showing no significant inhibition of human 15-lipoxygenase or porcine 12-lipoxygenase or binding to human 5-lipoxygenase-activating protein up to 10 mu M and inhibits leukotriene biosynthesis by a direct, nonredox interaction with 5-LO. Compound 15, the open form of lactone 4b, is well absorbed in the rat and is transformed into the active species 4b. In addition, 15 is orally active in the rat pleurisy model (ED(50) = 0.6 mg/kg) and in the functional model of antigen-induced bronchoconstriction in allergic squirrel monkeys (95% inhibition at 0.3 mg/kg).

  DOI：

  10.1021/jm00030a010
• 作为产物：
  描述：

  (3-oxo-9-phenyl-1H-benzo[f][2]benzofuran-6-yl) trifluoromethanesulfonate 在 1,1'-双(二苯基膦)二茂铁 、 palladium diacetate 、 lithium hydroxide 、 sodium tetrahydroborate 、 氯甲酸异丙酯 、 三乙胺 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.33h， 生成 7-(hydroxymethyl)-4-phenylnaphtho<2,3-c>furan-1(3H)-one
  参考文献：
  名称：

  Naphthalenic Lignan Lactones as Selective, Nonredox 5-Lipoxygenase Inhibitors. Synthesis and Biological Activity of (Methoxyalkyl)thiazole and Methoxytetrahydropyran Hybrids

  摘要：

  Combinations of structural elements found in (methoxyalkyl)thiazole 1a and methoxytetrahydropyran 2a with a naphthalenic lignan lactone produce the potent 5-lipoxygenase (5-LO) inhibitors 3 and 4. While the nature of link Y-Z has a major effect on the in vitro activity of compounds 1 and 2, inhibitors 3 and 4 retain their potencies with either an oxymethylene (Y = O, Z = CH2) or a methyleneoxy (Y = CH2, Z = O) link. Compound 4b inhibits the oxidation of arachidonic acid to 5-hydroperoxyeicosatetraenoic acid by 5-LO (IC50 = 14 nM) and the formation of leukotriene Bq in human polymorphonuclear leukocytes (IC50 = 1.5 nM) as well as in human whole blood (IC50 = 50 nM). Compound 4b is a selective 5-LO inhibitor showing no significant inhibition of human 15-lipoxygenase or porcine 12-lipoxygenase or binding to human 5-lipoxygenase-activating protein up to 10 mu M and inhibits leukotriene biosynthesis by a direct, nonredox interaction with 5-LO. Compound 15, the open form of lactone 4b, is well absorbed in the rat and is transformed into the active species 4b. In addition, 15 is orally active in the rat pleurisy model (ED(50) = 0.6 mg/kg) and in the functional model of antigen-induced bronchoconstriction in allergic squirrel monkeys (95% inhibition at 0.3 mg/kg).

  DOI：

  10.1021/jm00030a010

文献信息

• Ducharme Yves, Brideau Christine, Dube Daniel, Chan Chi-Chung, Falgueyret+, J. Med. Chem, 37 (1994) N 4, S 512-518
  作者：Ducharme Yves, Brideau Christine, Dube Daniel, Chan Chi-Chung, Falgueyret+

  DOI：——

  日期：——
• Naphthalenic Lignan Lactones as Selective, Nonredox 5-Lipoxygenase Inhibitors. Synthesis and Biological Activity of (Methoxyalkyl)thiazole and Methoxytetrahydropyran Hybrids
  作者：Yves Ducharme、Christine Brideau、Daniel Dube、Chi Chung Chan、Jean Pierre Falgueyret、John W. Gillard、Jocelyne Guay、John H. Hutchinson、Cyryl S. McFarlane

  DOI：10.1021/jm00030a010

  日期：1994.2

  Combinations of structural elements found in (methoxyalkyl)thiazole 1a and methoxytetrahydropyran 2a with a naphthalenic lignan lactone produce the potent 5-lipoxygenase (5-LO) inhibitors 3 and 4. While the nature of link Y-Z has a major effect on the in vitro activity of compounds 1 and 2, inhibitors 3 and 4 retain their potencies with either an oxymethylene (Y = O, Z = CH2) or a methyleneoxy (Y = CH2, Z = O) link. Compound 4b inhibits the oxidation of arachidonic acid to 5-hydroperoxyeicosatetraenoic acid by 5-LO (IC50 = 14 nM) and the formation of leukotriene Bq in human polymorphonuclear leukocytes (IC50 = 1.5 nM) as well as in human whole blood (IC50 = 50 nM). Compound 4b is a selective 5-LO inhibitor showing no significant inhibition of human 15-lipoxygenase or porcine 12-lipoxygenase or binding to human 5-lipoxygenase-activating protein up to 10 mu M and inhibits leukotriene biosynthesis by a direct, nonredox interaction with 5-LO. Compound 15, the open form of lactone 4b, is well absorbed in the rat and is transformed into the active species 4b. In addition, 15 is orally active in the rat pleurisy model (ED(50) = 0.6 mg/kg) and in the functional model of antigen-induced bronchoconstriction in allergic squirrel monkeys (95% inhibition at 0.3 mg/kg).