(4',11'-dimethyl-2'-oxo-6',7',8',9'-tetrahydrobenzofuro-[3,2-g]-1-benzopyran-3'-yl)propionic acid | 777857-61-1

• 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',11'-dimethyl-2'-oxo-6',7',8',9'-tetrahydrobenzofuro-[3,2-g]-1-benzopyran-3'-yl)propionic acid
• 英文别名: 3-{4',11'-dimethyl-2'-oxo-6',7',8',9'-tetrahydrobenzo[4,5]furo[3,2-g]chromen-3'-yl}propanoic acid；3-(4,11-dimethyl-2-oxo-6,7,8,9-tetrahydro-2H-[1]benzofuro[3,2-g]chromen-3-yl)propanoic acid；3-(4,11-dimethyl-2-oxo-6,7,8,9-tetrahydro-[1]benzofuro[3,2-g]chromen-3-yl)propanoic acid
• CAS: 777857-61-1
• 化学式: C₂₀H₂₀O₅
• mdl: MFCD03853835
• 分子量: 340.376
• InChiKey: LTNQBFQMHGWUED-UHFFFAOYSA-N

物化性质

• 熔点：
  245-246 °C(Solv: isopropanol (67-63-0))
• 沸点：
  575.4±50.0 °C(Predicted)
• 密度：
  1.300±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  76.7
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  (4',11'-dimethyl-2'-oxo-6',7',8',9'-tetrahydrobenzofuro-[3,2-g]-1-benzopyran-3'-yl)propionic acid 在 氯化亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 3.0h， 生成 3-(4,11-dimethyl-2-oxo-6,7,8,9-tetrahydro-[1]benzofuro[3,2-g]chromen-3-yl)-N-(4-hydroxyphenyl)propanamide
  参考文献：
  名称：

  Psoralen Derivatives as Inhibitors of NF-κB/DNA Interaction: Synthesis, Molecular Modeling, 3D-QSAR, and Biological Evaluation

  摘要：

  Some new psoralen derivatives were synthesized and evaluated as inhibitors of NF-kappa B/DNA interaction, with the aim to investigate the structural determinants required to inhibit this interaction. Starting from molecular docking studies, several possible protein binding sites were proposed and several three-dimensional quantitative structure activity relationship (3D-QSAR) models were built using the docked poses of 29 (the most active psoralen in the series) as templates for alignment of the inhibitors. The selected best model was validated through the prediction of the activity of 17 novel compounds. All the experimental data agreed with the computational experiments, supporting the reliability of the computational approach. The hypothesis about the interaction with NF-kappa B was also supported by surface plasmon resonance based assays using compound 29. All the collected data allowed the identification of compound 29 as a potential candidate for the development of pharmaceutical strategies against the inflammatory phenotype of cystic fibrosis.

  DOI：

  10.1021/jm3009647
• 作为产物：
  描述：

  乙酰戊二酸二乙酯 在 盐酸 、 sodium hydroxide 、 sodium carbonate 作用下， 以 乙醇 、 丙酮 为溶剂， 生成 (4',11'-dimethyl-2'-oxo-6',7',8',9'-tetrahydrobenzofuro-[3,2-g]-1-benzopyran-3'-yl)propionic acid
  参考文献：
  名称：

  修饰的补骨脂素类似物的合成

  摘要：

  通过将呋喃部分线性环化到香豆素体系中，合成类似于补骨脂素的3-（5-甲基-7-氧杂呋喃[3,2-g] chromen-6-基）丙酸。该论文的英文版：Russian Journal of Bioorganic Chemistry，2004年，第1卷。30号 3; 另请参见http://www.maik.ru。

  DOI：

  10.1023/b:rubi.0000030137.88504.10

文献信息

• Modified Coumarins. 33. Synthesis of Furo- and Dihydropyranocoumarins Containing a Lupinine Moiety
  作者：Yu. A. Nikitina、A. I. Galaev、Ya. L. Garazd、M. M. Garazd、V. G. Kartsev

  DOI：10.1007/s10600-015-1423-4

  日期：2015.9

  New coumarin derivatives containing a lupinine moiety were synthesized via amidation of furocoumarinylacetic, furocoumarinylpropionic, and dihydropyranocoumarinyloxyacetic acids with lupinylamine.

  通过呋喃香豆素乙酸、呋喃香豆素丙酸和二氢吡喃香豆素氧乙酸与羽扇豆胺的酰胺化反应，合成了含有羽扇豆碱分子的新型香豆素衍生物。
• Modified coumarins. 20. Furocoumarin derivatives of cytisine
  作者：M. V. Veselovskaya、M. M. Garazd、V. I. Vinogradova、V. P. Khilya

  DOI：10.1007/s10600-006-0098-2

  日期：2006.5

  Cytisine derivatives modified by furocoumarins were synthesized using activated esters.

  使用活化酯合成了呋喃香豆素修饰的金雀花碱衍生物。
• Synthesis of Modified Psoralen Analogues
  作者：M. M. Garazd、Ya. L. Garazd、A. S. Ogorodniichuk、V. P. Khilya

  DOI：10.1023/b:rubi.0000030137.88504.10

  日期：2004.5

  Substituted 3-(5-methyl-7-oxofuro[3,2-g]chromen-6-yl)propanoic acids analogous to psoralen were synthesized by linear annulation of a furan moiety to the coumarin system. The English version of the paper: Russian Journal of Bioorganic Chemistry, 2004, vol. 30, no. 3; see also http://www.maik.ru.

  通过将呋喃部分线性环化到香豆素体系中，合成类似于补骨脂素的3-（5-甲基-7-氧杂呋喃[3,2-g] chromen-6-基）丙酸。该论文的英文版：Russian Journal of Bioorganic Chemistry，2004年，第1卷。30号 3; 另请参见http://www.maik.ru。
• Psoralen Derivatives as Inhibitors of NF-κB/DNA Interaction: Synthesis, Molecular Modeling, 3D-QSAR, and Biological Evaluation
  作者：Giovanni Marzaro、Adriano Guiotto、Monica Borgatti、Alessia Finotti、Roberto Gambari、Giulia Breveglieri、Adriana Chilin

  DOI：10.1021/jm3009647

  日期：2013.3.14

  Some new psoralen derivatives were synthesized and evaluated as inhibitors of NF-kappa B/DNA interaction, with the aim to investigate the structural determinants required to inhibit this interaction. Starting from molecular docking studies, several possible protein binding sites were proposed and several three-dimensional quantitative structure activity relationship (3D-QSAR) models were built using the docked poses of 29 (the most active psoralen in the series) as templates for alignment of the inhibitors. The selected best model was validated through the prediction of the activity of 17 novel compounds. All the experimental data agreed with the computational experiments, supporting the reliability of the computational approach. The hypothesis about the interaction with NF-kappa B was also supported by surface plasmon resonance based assays using compound 29. All the collected data allowed the identification of compound 29 as a potential candidate for the development of pharmaceutical strategies against the inflammatory phenotype of cystic fibrosis.