2-bromooreoselon | 933457-27-3

• 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: 2-bromooreoselon
• 英文别名: 2-bromo-2-(1-methylethyl)-7H-furo[3,2-g][1]benzopyran-3,7-dione；2-bromooreoselone
• CAS: 933457-27-3
• 化学式: C₁₄H₁₁BrO₄
• 分子量: 323.143
• InChiKey: XOGDEUOBAPQZBV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.12
• 重原子数：
  19.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  56.51
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-bromooreoselon 在 氢氧化钾 作用下， 以 水 为溶剂， 反应 0.25h， 以83%的产率得到2-hydroxy-2-(1-methylethyl)-7H-furo[3,2-g][1]benzopyran-3,7-dione
  参考文献：
  名称：

  Study of plant coumarins 1. Transformations of peucedanin

  摘要：

  建立了前胡素或奥雷西隆与分子溴的溴化反应制备的2-溴奥雷西隆的结构。研究了该溴化物与吡啶、三乙胺和吗啉等胺以及与乙酸钠和氢氧化钾的反应产物的组成和结构。前胡素与间氯过苯甲酸反应得到前胡素异丁酸酯。

  DOI：

  10.1007/s11172-006-0263-6
• 作为产物：
  描述：

  oreoselone 在 溴 作用下， 以 氯仿 为溶剂， 生成 2-bromooreoselon
  参考文献：
  名称：

  Study of plant coumarins 1. Transformations of peucedanin

  摘要：

  建立了前胡素或奥雷西隆与分子溴的溴化反应制备的2-溴奥雷西隆的结构。研究了该溴化物与吡啶、三乙胺和吗啉等胺以及与乙酸钠和氢氧化钾的反应产物的组成和结构。前胡素与间氯过苯甲酸反应得到前胡素异丁酸酯。

  DOI：

  10.1007/s11172-006-0263-6

文献信息

• Synthesis of 1H-1,2,3-triazole linked aryl(arylamidomethyl) – dihydrofurocoumarin hybrids and analysis of their cytotoxicity
  作者：Alla V. Lipeeva、Mikhail A. Pokrovsky、Dmitry S. Baev、Makhmut M. Shakirov、Irina Y. Bagryanskaya、Tatijana G. Tolstikova、Andrey G. Pokrovsky、Elvira E. Shults

  DOI：10.1016/j.ejmech.2015.05.016

  日期：2015.7

  A series of 2-(4-R-triazolyl)substituted 3-oxo-2,3-dihydrofurocoumarins have been synthesized by a regioselective cycloaddition of 2-azidooreoselone 1 or 2-azido-9-[(4-methylpiperazin-1-yl)methyl] oreoselone 2 with various alkynes in the presence of Cu(II)/ascorbate in water/methylene chloride reaction medium. The structure of 2-azidooreoselone was established by X-ray structure analysis. The cytotoxicity of 2-substituted dihydrofurocoumarins was determined against three cancer cell lines (CEM-13, MT-4, U-937) using the conventional MTT assays. Among the tested molecules, most of the analogs displayed better cytotoxic activity then the parent natural furocoumarin peucedanin 3. The activity and selectivity to the cell line increased even further in the series of 2-(4-(2,3-dihydrobenzo[b][1,4]dioxine) triazolyl)-3-oxo-2,3-dihydrofurocoumarins and 2-(4-aryltriazolyl)-3-oxo-2,3-dihydrofurocoumarins having the (4-methylpiperazin-1-ylmethyl) substituent in the 9-th position. The most active compound 20 contain the 4-hydroxy-3-methoxybenzamidomethyl substituent in the 4-th position at the triazole ring of 2-(triazol-1-yl)dihydrofurocoumarins. The obtained 2-triazoly1 substituted dihydrofurocoumarins were studied as inhibitors of phosphodiesterase (PDE-4B) using docking experiments. As a result of virtual screening 3 compounds are selected based on minimum binding energy. The interactions of the most active compound and amino acid residues in the binding site were studied. (C) 2015 Elsevier Masson SAS. All rights reserved.