(3'-tert-butyl-5'-methyl-7'-oxo-7H-furo[3,2-g][1]benzopyran-6'-yl)propionic acid | 777857-43-9

• 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: (3'-tert-butyl-5'-methyl-7'-oxo-7H-furo[3,2-g][1]benzopyran-6'-yl)propionic acid
• 英文别名: 3-(3'-(tert-butyl)-5'-methyl-7'-oxofuro[3,2-g]chromen-6'-yl)propanoic acid；3-(3-tert-butyl-5-methyl-7-oxo-7H-furo[3,2-g]chromen-6-yl)propanoic acid；3-(3-tert-butyl-5-methyl-7-oxofuro[3,2-g]chromen-6-yl)propanoic acid
• CAS: 777857-43-9
• 化学式: C₁₉H₂₀O₅
• mdl: MFCD03851970
• 分子量: 328.365
• InChiKey: RSZGOILSNWBLCB-UHFFFAOYSA-N

物化性质

• 熔点：
  201-202 °C(Solv: isopropanol (67-63-0))
• 沸点：
  518.7±50.0 °C(Predicted)
• 密度：
  1.237±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 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：

  (3'-tert-butyl-5'-methyl-7'-oxo-7H-furo[3,2-g][1]benzopyran-6'-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 4-[[3-(3-Tert-butyl-5-methyl-7-oxofuro[3,2-g]chromen-6-yl)propanoylamino]methyl]benzoic acid
  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 (3'-tert-butyl-5'-methyl-7'-oxo-7H-furo[3,2-g][1]benzopyran-6'-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

• Nonpeptidic Selective Inhibitors of the Chymotrypsin-Like (β5 i) Subunit of the Immunoproteasome
  作者：Izidor Sosič、Martina Gobec、Boris Brus、Damijan Knez、Matej Živec、Janez Konc、Samo Lešnik、Mitja Ogrizek、Aleš Obreza、Dušan Žigon、Dušanka Janežič、Irena Mlinarič-Raščan、Stanislav Gobec

  DOI：10.1002/anie.201600190

  日期：2016.5.4

  of the immunoproteasome has been associated with autoimmune diseases, inflammatory diseases, and various types of cancer. Selective inhibitors of the immunoproteasome are not only scarce, but also almost entirely restricted to peptide‐based compounds. Herein, we describe nonpeptidic reversible inhibitors that selectively block the chymotrypsin‐like (β5i) subunit of the human immunoproteasome in the

  免疫蛋白酶体的高表达与自身免疫性疾病，炎性疾病和各种类型的癌症有关。免疫蛋白酶体的选择性抑制剂不仅稀缺，而且几乎完全限于基于肽的化合物。本文中，我们描述了非肽类可逆抑制剂，可在低微摩尔范围内选择性阻断人免疫蛋白酶体的胰凝乳蛋白酶样（β5i）亚基。然后将最有效的可逆作用化合物转化为共价，不可逆的非肽类抑制剂，这些抑制剂保留了对β5i亚基的选择性。此外，在基于细胞的测定中，这些抑制剂可区分免疫蛋白酶体和组成型蛋白酶体。除了缺乏细胞毒性外，