N-(3-hydroxy-9,10,11-trimethoxy-7-oxo-6,7-dihydro-5H-dibenzo[a,c][7]cyclohepten-5-yl)-2,2,2-trifluoroacetamide | 1373112-88-9

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 别秋水仙碱生物碱
• 英文名称: N-(3-hydroxy-9,10,11-trimethoxy-7-oxo-6,7-dihydro-5H-dibenzo[a,c][7]cyclohepten-5-yl)-2,2,2-trifluoroacetamide
• 英文别名: 2,2,2-trifluoro-N-(5-hydroxy-13,14,15-trimethoxy-10-oxo-8-tricyclo[9.4.0.02,7]pentadeca-1(15),2(7),3,5,11,13-hexaenyl)acetamide
• CAS: 1373112-88-9
• 化学式: C₂₀H₁₈F₃NO₆
• 分子量: 425.361
• InChiKey: JMIHJILAEYXWTJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  94.1
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  N-(3-hydroxy-9,10,11-trimethoxy-7-oxo-6,7-dihydro-5H-dibenzo[a,c][7]cyclohepten-5-yl)-2,2,2-trifluoroacetamide 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 (+/-)-trans-N-(3,7-dihydroxy-9,10,11-trimethoxy-6,7-dihydro-5H-di-benzo[a,c][7]cyclohepten-5-yl)-2,2,2-trifluoroacetamide 、 (+/-)-cis-N-(3,7-dihydroxy-9,10,11-trimethoxy-6,7-dihydro-5H-di-benzo[a,c][7]cyclohepten-5-yl)-2,2,2-trifluoroacetamide
  参考文献：
  名称：

  Synthesis of novel 7-oxo and 7-hydroxy trifluoroallocolchicinoids with cytotoxic effect

  摘要：

  The synthesis of 7-oxo and 7-hydroxy trifluoroallocolchicinoids was achieved through the intramolecular cyclization of o-phenyl-beta-phenylalanines. The resulting compounds were evaluated for their cytotoxic activity against KB cells and their inhibitory effect towards the polymerization of tubulin. The results yielded some potent cytotoxic compounds with correlated partial antitubulin effect. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.02.043
• 作为产物：
  描述：

  2-溴-5-羟基苯甲醛 在 四(三苯基膦)钯 、 potassium phosphate monohydrate 、 ammonium acetate 、 三氟乙酸 作用下， 以 乙二醇二甲醚 、 乙醇 为溶剂， 反应 25.5h， 生成 N-(3-hydroxy-9,10,11-trimethoxy-7-oxo-6,7-dihydro-5H-dibenzo[a,c][7]cyclohepten-5-yl)-2,2,2-trifluoroacetamide
  参考文献：
  名称：

  Synthesis of novel 7-oxo and 7-hydroxy trifluoroallocolchicinoids with cytotoxic effect

  摘要：

  The synthesis of 7-oxo and 7-hydroxy trifluoroallocolchicinoids was achieved through the intramolecular cyclization of o-phenyl-beta-phenylalanines. The resulting compounds were evaluated for their cytotoxic activity against KB cells and their inhibitory effect towards the polymerization of tubulin. The results yielded some potent cytotoxic compounds with correlated partial antitubulin effect. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.02.043

文献信息

• Synthesis of novel 7-oxo and 7-hydroxy trifluoroallocolchicinoids with cytotoxic effect
  作者：Elizabeth Chosson、Francesca Santoro、Christophe Rochais、Jana Sopkova-de Oliveira Santos、Rémi Legay、Sylviane Thoret、Thierry Cresteil、Maria Stefania Sinicropi、Thierry Besson、Patrick Dallemagne

  DOI：10.1016/j.bmc.2012.02.043

  日期：2012.4

  The synthesis of 7-oxo and 7-hydroxy trifluoroallocolchicinoids was achieved through the intramolecular cyclization of o-phenyl-beta-phenylalanines. The resulting compounds were evaluated for their cytotoxic activity against KB cells and their inhibitory effect towards the polymerization of tubulin. The results yielded some potent cytotoxic compounds with correlated partial antitubulin effect. (C) 2012 Elsevier Ltd. All rights reserved.