5-(hex-1-en-2-yl)-1,2,3-trimethoxybenzene | 1379793-82-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-(hex-1-en-2-yl)-1,2,3-trimethoxybenzene
• 英文别名: 5-Hex-1-en-2-yl-1,2,3-trimethoxybenzene
• CAS: 1379793-82-4
• 化学式: C₁₅H₂₂O₃
• 分子量: 250.338
• InChiKey: RIYTVXIOCSDZSJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(hex-1-en-2-yl)-1,2,3-trimethoxybenzene 、 二苯甲酰基甲烷 在 manganese triacetate 、 溶剂黄146 作用下， 反应 0.5h， 以31%的产率得到(5-butyl-2-phenyl-5-(3,4,5-trimethoxyphenyl)-4,5-dihydrofuran-3-yl)(phenyl)methanone
  参考文献：
  名称：

  Constructing novel dihydrofuran and dihydroisoxazole analogues of isocombretastatin-4 as tubulin polymerization inhibitors through [3+2] reactions

  摘要：

  [3+2] reactions play a key role in constructing various pharmaceutical moleculars. In this study, using Mn (OAc)(3) mediated and 1,3-dipolar [3+2] cyclization reactions, 38 novel dihydrofuran and dihydroisoxazole analogues of isoCA-4 were synthesized as inhibitors of tubulin polymerization. Among them, compound 6g was found to be the most potent cytotoxic agents against PC-3 cells with IC50 value of 0.47 mu M, and compound 5p exhibted highest activity on HeLa cells with IC50 vaule of 2.32 mu M. Tubulin polymerization assay revealed that 6g was a dose-dependent and effective inhibitor of tubulin assembly. Immunohistochemistry studies and cell cycle distribution analysis indicated that 6g severely disrupted microtubule network and significantly arrested most cells in the G2/M phase of the cell cycle in PC-3 cells. In addition, molecular docking studies showed that two chiral isomers of 6g can bind efficiently and similarly at colchicine binding site of tubulin. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2017.07.048
• 作为产物：
  描述：

  3',4',5'-三甲氧基苯乙酮 在 iron(III) chloride 、 噻吩-2-甲酸亚铜(I) 、 碘 、 三乙胺 、 肼 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 2.0h， 生成 5-(hex-1-en-2-yl)-1,2,3-trimethoxybenzene
  参考文献：
  名称：

  通过格氏试剂与1-芳基乙烯基卤化物的高效铁/铜共催化偶联合成1,1-二芳基乙烯

  摘要：

  描述了通过在FeCl 3 / CuTC存在下偶联官能化的芳基格氏试剂和1-芳基乙烯基卤化物来有效获得生物学上感兴趣的1，1-二芳基乙烯。事实证明，这种双金属系统优于单独使用Fe或Cu催化剂。该方案的合成用途在类固醇化学领域得到了说明。

  DOI：

  10.1021/ol3010112

文献信息

• Synthesis of 1,1-Diarylethylenes via Efficient Iron/Copper Co-Catalyzed Coupling of 1-Arylvinyl Halides with Grignard Reagents
  作者：Abdallah Hamze、Jean-Daniel Brion、Mouad Alami

  DOI：10.1021/ol3010112

  日期：2012.6.1

  An efficient access to 1,1-diarylethylenes of biological interest by coupling functionalized aryl Grignard reagents and 1-arylvinyl halides in the presence of FeCl3/CuTC is described. This bimetallic system proved to be superior to the use of Fe or Cu catalyst alone. The synthetic utility of this protocol is illustrated in the field of steroid chemistry.

  描述了通过在FeCl 3 / CuTC存在下偶联官能化的芳基格氏试剂和1-芳基乙烯基卤化物来有效获得生物学上感兴趣的1，1-二芳基乙烯。事实证明，这种双金属系统优于单独使用Fe或Cu催化剂。该方案的合成用途在类固醇化学领域得到了说明。
• Constructing novel dihydrofuran and dihydroisoxazole analogues of isocombretastatin-4 as tubulin polymerization inhibitors through [3+2] reactions
  作者：Ming-Yu Song、Chen-Yu Cao、Qiu-Rui He、Qing-Miao Dong、Ding Li、Jiang-Jiang Tang、Jin-Ming Gao

  DOI：10.1016/j.bmc.2017.07.048

  日期：2017.10

  [3+2] reactions play a key role in constructing various pharmaceutical moleculars. In this study, using Mn (OAc)(3) mediated and 1,3-dipolar [3+2] cyclization reactions, 38 novel dihydrofuran and dihydroisoxazole analogues of isoCA-4 were synthesized as inhibitors of tubulin polymerization. Among them, compound 6g was found to be the most potent cytotoxic agents against PC-3 cells with IC50 value of 0.47 mu M, and compound 5p exhibted highest activity on HeLa cells with IC50 vaule of 2.32 mu M. Tubulin polymerization assay revealed that 6g was a dose-dependent and effective inhibitor of tubulin assembly. Immunohistochemistry studies and cell cycle distribution analysis indicated that 6g severely disrupted microtubule network and significantly arrested most cells in the G2/M phase of the cell cycle in PC-3 cells. In addition, molecular docking studies showed that two chiral isomers of 6g can bind efficiently and similarly at colchicine binding site of tubulin. (C) 2017 Elsevier Ltd. All rights reserved.