N-[1-[3-[tert-butyl(dimethyl)silyl]oxy-4,5-dimethoxyphenyl]ethylideneamino]-4-methylbenzenesulfonamide | 1170045-92-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-[1-[3-[tert-butyl(dimethyl)silyl]oxy-4,5-dimethoxyphenyl]ethylideneamino]-4-methylbenzenesulfonamide
• CAS: 1170045-92-7
• 化学式: C₂₃H₃₄N₂O₅SSi
• 分子量: 478.685
• InChiKey: XAUQAWMMIKCLQB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  32.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  86.22
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  N-[1-[3-[tert-butyl(dimethyl)silyl]oxy-4,5-dimethoxyphenyl]ethylideneamino]-4-methylbenzenesulfonamide 、 4-碘藜芦醚 在 tris-(dibenzylideneacetone)dipalladium(0) 、 lithium tert-butoxide 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 1,4-二氧六环 为溶剂， 生成
  参考文献：
  名称：

  Isocombretastatins A versus Combretastatins A: The Forgotten isoCA-4 Isomer as a Highly Promising Cytotoxic and Antitubulin Agent

  摘要：

  Herein is reported a convergent synthesis of isocombretastatins A, a novel class of potent antitubulin agents. These compounds having a 1,1-diarylethylene scaffold constitute the simplest isomers of natural Z-combretastatins A that are easy to synthesize without need to control the Z-olefin geometry. The discovery of isoCA-4 with biological activities comparable to that of CA-4 represents a major progress in this field.

  DOI：

  10.1021/jm900321u
• 作为产物：
  描述：

  1-[3-(tert-butyldimethylsilanyloxy)-4,5-dimethoxyphenyl]ethanone 、 对甲苯磺酰肼 以 乙醇 为溶剂， 以83%的产率得到N-[1-[3-[tert-butyl(dimethyl)silyl]oxy-4,5-dimethoxyphenyl]ethylideneamino]-4-methylbenzenesulfonamide
  参考文献：
  名称：

  Isocombretastatins A versus Combretastatins A: The Forgotten isoCA-4 Isomer as a Highly Promising Cytotoxic and Antitubulin Agent

  摘要：

  Herein is reported a convergent synthesis of isocombretastatins A, a novel class of potent antitubulin agents. These compounds having a 1,1-diarylethylene scaffold constitute the simplest isomers of natural Z-combretastatins A that are easy to synthesize without need to control the Z-olefin geometry. The discovery of isoCA-4 with biological activities comparable to that of CA-4 represents a major progress in this field.

  DOI：

  10.1021/jm900321u

文献信息

• The Metabolic Fate of isoCombretastatin A-4 in Human Liver Microsomes: Identification, Synthesis and Biological Evaluation of Metabolites
  作者：Mohamed Ali Soussi、Silvio Aprile、Samir Messaoudi、Olivier Provot、Erika Del Grosso、Jérôme Bignon、Joëlle Dubois、Jean-Daniel Brion、Giorgio Grosa、Mouad Alami

  DOI：10.1002/cmdc.201100193

  日期：2011.10.4

  the structural differences between isocombretastatin A‐4 (isoCA‐4) bearing a 1,1‐diarylethylene scaffold and the natural Z‐stilbene combretastatin A‐4 (CA‐4), we examined the metabolic profile of isoCA‐4 using human liver fractions. Seven isoCA‐4 metabolites, resulting from O‐demethylation, hydroxylation of the aromatic rings were identified and synthesized. Evaluation of their cytotoxicity and their

  消化药物！由于带有1,1-二芳基乙烯支架的iso combretastatin A-4（iso CA-4）与天然Z -stilbene combretastatin A-4（CA-4）之间的结构差异，我们检查了iso CA‐ 4．使用人肝馏分。鉴定并合成了由O-去甲基化，芳环羟基化产生的7种iso CA-4代谢产物。对它们的细胞毒性及其抑制微管蛋白聚合（ITP活性）的能力的评估使我们鉴定出了具有与iso CA-4相当的强抗有丝分裂活性的代谢物。