4-(chloromethyl)-6,7-dimethoxy-2H-chromen-2-one | 197591-05-2

• 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: 4-(chloromethyl)-6,7-dimethoxy-2H-chromen-2-one
• 英文别名: 4-chloromethyl-6,7-dimethoxycoumarin；2H-1-Benzopyran-2-one, 4-(chloromethyl)-6,7-dimethoxy-；4-(chloromethyl)-6,7-dimethoxychromen-2-one
• CAS: 197591-05-2
• 化学式: C₁₂H₁₁ClO₄
• 分子量: 254.67
• InChiKey: JUINCLWPPKPHNW-UHFFFAOYSA-N

物化性质

• 熔点：
  204.5-205.5 °C
• 沸点：
  405.4±45.0 °C(Predicted)
• 密度：
  1.302±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(chloromethyl)-6,7-dimethoxy-2H-chromen-2-one 在 正丁基锂 、 oxonium 作用下， 以 四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  L-(6,7-dimethoxy-4-coumaryl) alanine: an intrinsic probe for the labelling of peptides

  摘要：

  The asymmetric synthesis, spectral properties and incorporation into solid phase peptide synthesis are described for L-(6,7-dimethoxy-4-coumaryl)alanine (Dca). Dca has great utility as a specific and highly sensitive intrinsic probe for fluorescence labelling and quantitation of peptides and proteins. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)01753-x
• 作为产物：
  描述：

  3,4-二甲氧基苯酚 、 4-氯乙酰乙酸乙酯 在 Amberlyst-15 cation-exchange resin 作用下， 以 甲苯 为溶剂， 以61%的产率得到4-(chloromethyl)-6,7-dimethoxy-2H-chromen-2-one
  参考文献：
  名称：

  Design, Synthesis, Physicochemical Properties, and Evaluation of Novel Iron Chelators with Fluorescent Sensors

  摘要：

  The synthesis of a range of novel 3-hydroxypyridin-4-ones and 3-hydroxypyran-4-ones linked with different coumarin substituents is described. These compounds have been developed in order to provide a series of molecular probes for the quantification of intracellular labile iron pools. An evaluation of the effect of iron(III) on fluorescence intensity was undertaken. Chelation of iron(III) causes quenching of fluorescence. The relationship between iron(III) concentration and the extent of fluorescence quenching indicates that the metal is chelated in a complex with a metal-to-ligand stoichiometry of 1:3. The fluorescence of hydroxypyridinone compounds was found to be more efficiently quenched by iron(III) than were the hydroxypyranones. The metal-to-ligand stoichiometry at which maximum quenching is observed was found to depend on the site at which coumarin is attached. The efficiency of fluorescence quenching by iron(III) is markedly influenced by solvent polarity and pH. The permeability of two representative fluorescent chelators across human erythrocyte ghost membranes was investigated. The rate of permeability for a series of probes was found to be related to the corresponding ClogP values.

  DOI：

  10.1021/jm049751s

文献信息

• Preliminary Structure–Antiangiogenic Activity Relationships of 4-Senecioyloxymethyl-6,7-dimethoxycoumarin
  作者：Nguyen-Hai Nam、Yong Kim、Young-Jae You、Dong-Ho Hong、Hwan-Mook Kim、Byung-Zun Ahn

  DOI：10.1016/s0960-894x(02)00392-x

  日期：2002.9

  Through a systematic modification of the novel angiogenesis inhibitor 4-senecioyloxymethyl-6,7-dimethoxycoumarin (1) we found that a 6,7-dimethoxy moiety is important for bioactivity of 1. Replacement of the lactone functionality in coumarin 1 by an amide decreased its activity. By substitution of the senecioyl chain with various cinnamoyl groups we discovered 6d, bearing a 4-methoxycinnamoyl instead of senecioyl side chain, with inhibitory activity in HUVEC tube formation assay enhanced by one order of magnitude compared to 1. We have also synthesized compound 12, an analogue of 6d, with equipotency and improved water solubility. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Design, Synthesis, Physicochemical Properties, and Evaluation of Novel Iron Chelators with Fluorescent Sensors
  作者：Yongmin Ma、Wei Luo、Peter J. Quinn、Zudong Liu、Robert C. Hider

  DOI：10.1021/jm049751s

  日期：2004.12.1

  The synthesis of a range of novel 3-hydroxypyridin-4-ones and 3-hydroxypyran-4-ones linked with different coumarin substituents is described. These compounds have been developed in order to provide a series of molecular probes for the quantification of intracellular labile iron pools. An evaluation of the effect of iron(III) on fluorescence intensity was undertaken. Chelation of iron(III) causes quenching of fluorescence. The relationship between iron(III) concentration and the extent of fluorescence quenching indicates that the metal is chelated in a complex with a metal-to-ligand stoichiometry of 1:3. The fluorescence of hydroxypyridinone compounds was found to be more efficiently quenched by iron(III) than were the hydroxypyranones. The metal-to-ligand stoichiometry at which maximum quenching is observed was found to depend on the site at which coumarin is attached. The efficiency of fluorescence quenching by iron(III) is markedly influenced by solvent polarity and pH. The permeability of two representative fluorescent chelators across human erythrocyte ghost membranes was investigated. The rate of permeability for a series of probes was found to be related to the corresponding ClogP values.
• L-(6,7-dimethoxy-4-coumaryl) alanine: an intrinsic probe for the labelling of peptides
  作者：Fiona A. Bennett、David J. Barlow、Alexander N.O. Dodoo、Robert C. Hider、Alison B. Lansley、M.Jayne Lawrence、Christopher Marriott、Sukhvinder S. Bansal

  DOI：10.1016/s0040-4039(97)01753-x

  日期：1997.10

  The asymmetric synthesis, spectral properties and incorporation into solid phase peptide synthesis are described for L-(6,7-dimethoxy-4-coumaryl)alanine (Dca). Dca has great utility as a specific and highly sensitive intrinsic probe for fluorescence labelling and quantitation of peptides and proteins. (C) 1997 Elsevier Science Ltd.