N-[1-(7-methoxy-1,3-benzodioxol-5-yl)ethylideneamino]-4-methylbenzenesulfonamide | 1170045-89-2

• 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-(7-methoxy-1,3-benzodioxol-5-yl)ethylideneamino]-4-methylbenzenesulfonamide
• CAS: 1170045-89-2
• 化学式: C₁₇H₁₈N₂O₅S
• 分子量: 362.406
• InChiKey: HYBHAALAHUFJFC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.43
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 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-(7-methoxy-1,3-benzodioxol-5-yl)ethylideneamino]-4-methylbenzenesulfonamide 、 3-(tert-butyldimethylsilyloxy)-4-methyloxyphenyl iodide 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 C₂₃H₃₀O₅Si
  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：

  5'-甲氧基-3',4'-亚甲二氧基苯乙酮 、 对甲苯磺酰肼 以 乙醇 为溶剂， 以79%的产率得到N-[1-(7-methoxy-1,3-benzodioxol-5-yl)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

• Discovery of Isoerianin Analogues as Promising Anticancer Agents
  作者：Samir Messaoudi、Abdallah Hamze、Olivier Provot、Bret Tréguier、Jordi Rodrigo De Losada、Jérôme Bignon、Jian‐Miao Liu、Joanna Wdzieczak‐Bakala、Sylviane Thoret、Joëlle Dubois、Jean‐Daniel Brion、Mouad Alami

  DOI：10.1002/cmdc.201000456

  日期：2011.3.7

  activity of a series of 23 new isoerianin derivatives with modifications on both the A and B rings was studied. Several compounds exhibited excellent antiproliferative activity at nanomolar concentrations against a panel of human cancer cell lines. The most cytotoxic compound, isoerianin (3), strongly inhibits tubulin polymerization in the micromolar range. Moreover, isoerianin leads to G2/M phase cell‐cycle

  研究了一系列23种在A和B环上都进行了修饰的新异麦草精衍生物的细胞毒活性。几种化合物在纳摩尔浓度下对一组人类癌细胞系均表现出优异的抗增殖活性。最具细胞毒性的化合物异麦尿素（3）在微摩尔范围内强烈抑制微管蛋白的聚合。此外，异胡芦精导致G 2/ M期细胞周期在H1299和K562癌细胞中停滞，并强烈诱导细胞凋亡。异叶菌素还可以在体外破坏人脐静脉内皮细胞（HUVEC）形成的血管样结构，这表明该化合物可能起血管破坏剂的作用。显然，在该化合物系列中，异亮氨酸衍生物中遇到的1,1-乙烷桥可取代天然亚麻酸的1,2-乙烷桥，而不会丧失活性。这加强了我们研究小组先前报道的康维他汀系列中的生物立体替代疗法。