2-isopropyl-9-((4-methylpiperazin-1-yl)methyl)-7-oxo-7H-furo[3,2-g]chromen-3-yl trifluoromethanesulfonate | 1430731-93-3

• 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-isopropyl-9-((4-methylpiperazin-1-yl)methyl)-7-oxo-7H-furo[3,2-g]chromen-3-yl trifluoromethanesulfonate
• 英文别名: 2-isopropyl-9-[(4-methylpiperazin-1-yl)methyl]-7-oxo-7H-furo[3,2-g]chromen-3-yl trifluoromethanesulfonate；2-Isopropyl-9-[(4-methylpiperazin-1-yl)methyl]-7-oxo-7h-furo[3,2-g]chromen-3-yl trifluorometh-anesulfonate；[9-[(4-methylpiperazin-1-yl)methyl]-7-oxo-2-propan-2-ylfuro[3,2-g]chromen-3-yl] trifluoromethanesulfonate
• CAS: 1430731-93-3
• 化学式: C₂₁H₂₃F₃N₂O₆S
• 分子量: 488.485
• InChiKey: DXWBWAKURAPDCK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  97.7
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2-isopropyl-9-((4-methylpiperazin-1-yl)methyl)-7-oxo-7H-furo[3,2-g]chromen-3-yl trifluoromethanesulfonate 、 2-甲基苯硼酸 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 四丁基溴化铵 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 5.0h， 以80%的产率得到2-isopropyl-9-[(4-methylpiperazin-1-yl)methyl]-3-(2-methylphenyl)-7H-furo[3,2-g]chromen-7-one
  参考文献：
  名称：

  Plant coumarins: XIII. Synthesis of 2,3,9-trisubstituted furocoumarins

  摘要：

  Peucedanin reacted with methylideneiminium salt generated in situ from N,N,N',N'-tetramethylmethanediamine and acetyl chloride to give 2-(dimethylaminomethyl)oreoselone. Reactions of peucedanin with aminomethylating agents generated in situ from formaldehyde and dimethylamine, N-methylpiperazine, or N-Boc-piperazine in boiling methanol smoothly afforded the corresponding 9-aminomethyl derivatives whose hydrolysis produced 9-aminomethyl-substituted oreoselones. 2,3,9-Trisubstituted linearly fused furocoumarins were synthesized by reactions of 9-substituted oreoselone trifluoromethanesulfonates with arylboronic acids.

  DOI：

  10.1134/s1070428013030159
• 作为产物：
  描述：

  3-甲氧基-2-丙-2-基呋喃并[3,2-g]苯并吡喃-7-酮 在 吡啶 、 盐酸 、 水 作用下， 以 甲醇 为溶剂， 反应 41.5h， 生成 2-isopropyl-9-((4-methylpiperazin-1-yl)methyl)-7-oxo-7H-furo[3,2-g]chromen-3-yl trifluoromethanesulfonate
  参考文献：
  名称：

  Plant coumarins: XIII. Synthesis of 2,3,9-trisubstituted furocoumarins

  摘要：

  Peucedanin reacted with methylideneiminium salt generated in situ from N,N,N',N'-tetramethylmethanediamine and acetyl chloride to give 2-(dimethylaminomethyl)oreoselone. Reactions of peucedanin with aminomethylating agents generated in situ from formaldehyde and dimethylamine, N-methylpiperazine, or N-Boc-piperazine in boiling methanol smoothly afforded the corresponding 9-aminomethyl derivatives whose hydrolysis produced 9-aminomethyl-substituted oreoselones. 2,3,9-Trisubstituted linearly fused furocoumarins were synthesized by reactions of 9-substituted oreoselone trifluoromethanesulfonates with arylboronic acids.

  DOI：

  10.1134/s1070428013030159

文献信息

• Synthesis and Cytotoxic Activity of a New Group of Heterocyclic Analogues of the Combretastatins
  作者：Alla Lipeeva、Elvira Shults、Makhmut Shakirov、Mikhail Pokrovsky、Andrey Pokrovsky

  DOI：10.3390/molecules19067881

  日期：——

  A series of new analogs of combretastatin A-4 (CA-4, 1) with the A or B-ring replaced by a 3-oxo-2,3-dihydrofurocoumarin or a furocoumarin residue have been designed and synthesized by employing a cross-coupling approach. All the compounds were evaluated for their cytotoxic activity with respect to model cancer cell lines (CEM-13, MT-4, U-937) using conventional MTT assays. Structure-activity relationship

  一系列新的考布他汀 A-4 类似物 (CA-4, 1) 的 A 或 B 环被 3-氧代-2,3-二氢呋喃香豆素或呋喃香豆素残基取代，已通过使用交叉设计和合成。耦合方法。使用常规 MTT 测定法评估所有化合物对模型癌细胞系（CEM-13、MT-4、U-937）的细胞毒活性。构效关系分析表明，其中 (Z)-苯乙烯基取代基连接到 3-oxo-2,3-dihydrofurocoumarin 核心的 2-位的化合物 2, 3, 6-8 与 3 -(Z)-苯乙烯基呋喃香豆素 4、5、9-11。(Z)-苯乙烯基部分的芳环上的甲氧基、羟基和甲酰基取代似乎在此类化合物中起重要作用。化合物 2 和 3 对 CEM-13 细胞系显示出最佳效力，CTD50 值范围为 4.9 至 5.1 μM。与 CA-4 相比，所有合成的化合物对 T 细胞人类白血病细胞 MT-4 和淋巴母细胞白血病细胞 CEM-13 都表现出中