4-(3'-bromo-4',5'-dimethoxyphenyl)-5-(4''-methoxy-3''-tetrahydropyranyloxyphenyl)-oxazole | 1257227-18-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(3'-bromo-4',5'-dimethoxyphenyl)-5-(4''-methoxy-3''-tetrahydropyranyloxyphenyl)-oxazole
• 英文别名: 4-(3-Bromo-4,5-dimethoxyphenyl)-5-[4-methoxy-3-(oxan-2-yloxy)phenyl]-1,3-oxazole
• CAS: 1257227-18-1
• 化学式: C₂₃H₂₄BrNO₆
• 分子量: 490.351
• InChiKey: ZFUCFLCHYHANTN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  72.2
• 氢给体数：
  0
• 氢受体数：
  7

上下游信息

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	4-(3'-bromo-4',5'-dimethoxyphenyl)-5-(3''-hydroxy-4''-methoxyphenyl)-oxazole	1257227-20-5	C18H16BrNO5	406.233

反应信息

• 作为反应物：
  描述：

  4-(3'-bromo-4',5'-dimethoxyphenyl)-5-(4''-methoxy-3''-tetrahydropyranyloxyphenyl)-oxazole 在 4-甲基苯磺酸吡啶 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以93%的产率得到4-(3'-bromo-4',5'-dimethoxyphenyl)-5-(3''-hydroxy-4''-methoxyphenyl)-oxazole
  参考文献：
  名称：

  Ru(η6-arene) complexes of combretastatin-analogous oxazoles with enhanced anti-tumoral impact

  摘要：

  Oxazole-bridged combretastatin A-4 analogues bind to tubulin and exert anti-vascular and anti-angiogenic effects. When linked to Ru(eta(6)-arene) complex fragments, conjugates with additional cytotoxic activity result which can ruthenate bionucleophiles such as DNA and proteins. For instance, the Ru(11) (p-cymene)(isonicotinate)Cl-2 complex 6a of the known 4-(3,4,5-trimethoxyphenyl)-5-(3-hydroxy-4-methoxyphenyl)-oxazole 4a was far more active than the latter against cells of the p53-competent wild-type form of HCT-116 colon carcinoma at low 0.01 mu M concentrations. A fast reaction of 6a with nucleophilic N-acetyl-L-cysteine was observed in NMR studies. The Ru(arene) complexes 6a-c were also more efficacious against combretastatin-refractory p53(+) cells of human HT-29 colon carcinoma when compared to their parent 4-(3,4-dimethoxy-5-methoxy/halo-phenyl)-5-(3-hydroxy-4-methoxyphenyl)-oxazoles 4a-c. These cells are rich in ABC-transporters which are responsible for their multi-drug resistance and for which conjugates 6 are less good substrates than the phenols 4. Unlike 4a, its complex 6a also diminished the motility of human 518A2 melanoma cells in a wound-healing assay which is indicative of anti-metastatic activity in solid tumors. Overall, the Ru(arene) complex conjugates 6 broaden the anti-tumoral spectrum of the combretastatin A-4 analogues 4 considerably. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.07.061
• 作为产物：
  描述：

  4-methoxy-3-(tetrahydro-2H-pyran-2-yloxy)benzaldehyde 、 3-bromo-4,5-dimethoxyphenyl(tosyl)methyl isocyanide 在 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 以45%的产率得到4-(3'-bromo-4',5'-dimethoxyphenyl)-5-(4''-methoxy-3''-tetrahydropyranyloxyphenyl)-oxazole
  参考文献：
  名称：

  Ru(η6-arene) complexes of combretastatin-analogous oxazoles with enhanced anti-tumoral impact

  摘要：

  Oxazole-bridged combretastatin A-4 analogues bind to tubulin and exert anti-vascular and anti-angiogenic effects. When linked to Ru(eta(6)-arene) complex fragments, conjugates with additional cytotoxic activity result which can ruthenate bionucleophiles such as DNA and proteins. For instance, the Ru(11) (p-cymene)(isonicotinate)Cl-2 complex 6a of the known 4-(3,4,5-trimethoxyphenyl)-5-(3-hydroxy-4-methoxyphenyl)-oxazole 4a was far more active than the latter against cells of the p53-competent wild-type form of HCT-116 colon carcinoma at low 0.01 mu M concentrations. A fast reaction of 6a with nucleophilic N-acetyl-L-cysteine was observed in NMR studies. The Ru(arene) complexes 6a-c were also more efficacious against combretastatin-refractory p53(+) cells of human HT-29 colon carcinoma when compared to their parent 4-(3,4-dimethoxy-5-methoxy/halo-phenyl)-5-(3-hydroxy-4-methoxyphenyl)-oxazoles 4a-c. These cells are rich in ABC-transporters which are responsible for their multi-drug resistance and for which conjugates 6 are less good substrates than the phenols 4. Unlike 4a, its complex 6a also diminished the motility of human 518A2 melanoma cells in a wound-healing assay which is indicative of anti-metastatic activity in solid tumors. Overall, the Ru(arene) complex conjugates 6 broaden the anti-tumoral spectrum of the combretastatin A-4 analogues 4 considerably. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.07.061