2-((E)-1-Methoxycarbonyl-2-thiophen-2-yl-vinyl)-benzoic acid | 59417-09-3

• 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: 2-((E)-1-Methoxycarbonyl-2-thiophen-2-yl-vinyl)-benzoic acid
• 英文别名: 2-[(E)-3-methoxy-3-oxo-1-thiophen-2-ylprop-1-en-2-yl]benzoic acid
• CAS: 59417-09-3
• 化学式: C₁₅H₁₂O₄S
• 分子量: 288.324
• InChiKey: QXMJSKLQVYDUIM-UKTHLTGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  91.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-((E)-1-Methoxycarbonyl-2-thiophen-2-yl-vinyl)-benzoic acid 以62%的产率得到
  参考文献：
  名称：

  EL-RAYYES N. R.; ALI A. H. A., D1. J. HETEROCYCL. CHEM. , 1976, 13, NO 1, 83-88

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(2-甲氧基-2-氧代乙基)苯羧酸甲酯 、 2-噻吩甲醛 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 2-((E)-1-Methoxycarbonyl-2-thiophen-2-yl-vinyl)-benzoic acid
  参考文献：
  名称：

  New Analogues of Amonafide and Elinafide, Containing Aromatic Heterocycles:  Synthesis, Antitumor Activity, Molecular Modeling, and DNA Binding Properties

  摘要：

  Amonafide- and elinafide-related mono and bisintercalators, modified by the introduction of a, pi -excedent furan or thiophene ring fused to the naphthalimide moiety, have been synthesized. These compounds have shown an interesting antitumor profile. The best compound, 9, was 2.5-fold more potent than elinafide against human colon carcinoma cells (HT-29). Molecular dynamic simulations and physicochemical experiments have demonstrated that these compounds are capable of forming stable DNA complexes. These results, together with those previously reported by us for imidazo- and pyrazinonaphthalimide analogues, have prompted us to propose that the DNA binding process does not depend on the electronic nature of the fused heterocycle.

  DOI：

  10.1021/jm0308850

文献信息

• New Analogues of Amonafide and Elinafide, Containing Aromatic Heterocycles:  Synthesis, Antitumor Activity, Molecular Modeling, and DNA Binding Properties
  作者：Miguel F. Braña、Mónica Cacho、Mario A. García、Beatriz de Pascual-Teresa、Ana Ramos、M. Teresa Domínguez、José M. Pozuelo、Cristina Abradelo、María Fernanda Rey-Stolle、Mercedes Yuste、Mónica Báñez-Coronel、Juan Carlos Lacal

  DOI：10.1021/jm0308850

  日期：2004.3.1

  Amonafide- and elinafide-related mono and bisintercalators, modified by the introduction of a, pi -excedent furan or thiophene ring fused to the naphthalimide moiety, have been synthesized. These compounds have shown an interesting antitumor profile. The best compound, 9, was 2.5-fold more potent than elinafide against human colon carcinoma cells (HT-29). Molecular dynamic simulations and physicochemical experiments have demonstrated that these compounds are capable of forming stable DNA complexes. These results, together with those previously reported by us for imidazo- and pyrazinonaphthalimide analogues, have prompted us to propose that the DNA binding process does not depend on the electronic nature of the fused heterocycle.
• EL-RAYYES N. R.; ALI A. H. A., D1. J. HETEROCYCL. CHEM. <JHTC-AD>, 1976, 13, NO 1, 83-88
  作者：EL-RAYYES N. R.、 ALI A. H. A.

  DOI：——

  日期：——