(E)-2-isopropyl-2-(4-{[3-(2,4-dimethoxyphenyl)acrylamido]methyl}-1H-1,2,3-triazol-1-yl)-9-[(4-methylpiperazin-1-yl)methyl]-3,7-dihydro-2H-furo[3,2-g]chromene-3,7-dione | 1700661-40-0

• 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: (E)-2-isopropyl-2-(4-{[3-(2,4-dimethoxyphenyl)acrylamido]methyl}-1H-1,2,3-triazol-1-yl)-9-[(4-methylpiperazin-1-yl)methyl]-3,7-dihydro-2H-furo[3,2-g]chromene-3,7-dione
• 英文别名: (2E)-N-[[1-[2,3-Dihydro-2-(1-methylethyl)-9-[(4-methyl-1-piperazinyl)methyl]-3,7-dioxo-7H-furo[3,2-g][1]benzopyran-2-yl]-1H-1,2,3-triazol-4-yl]methyl]-3-(2,4-dimethoxyphenyl)-2-propenamide；(E)-3-(2,4-dimethoxyphenyl)-N-[[1-[9-[(4-methylpiperazin-1-yl)methyl]-3,7-dioxo-2-propan-2-ylfuro[3,2-g]chromen-2-yl]triazol-4-yl]methyl]prop-2-enamide
• CAS: 1700661-40-0
• 化学式: C₃₄H₃₈N₆O₇
• 分子量: 642.712
• InChiKey: SKAPTHYQYAAOEU-JXMROGBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  47
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  137
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  2-bromooreoselon 在 sodium azide 、 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 生成 (E)-2-isopropyl-2-(4-{[3-(2,4-dimethoxyphenyl)acrylamido]methyl}-1H-1,2,3-triazol-1-yl)-9-[(4-methylpiperazin-1-yl)methyl]-3,7-dihydro-2H-furo[3,2-g]chromene-3,7-dione
  参考文献：
  名称：

  Synthesis of 1H-1,2,3-triazole linked aryl(arylamidomethyl) – dihydrofurocoumarin hybrids and analysis of their cytotoxicity

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2015.05.016