3-(4-Methoxyphenyl)-4-(3,4,5-trimethoxyphenyl)furan | 910820-88-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: 3-(4-Methoxyphenyl)-4-(3,4,5-trimethoxyphenyl)furan
• CAS: 910820-88-1
• 化学式: C₂₀H₂₀O₅
• 分子量: 340.376
• InChiKey: LETFYOPOOTYLDT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(4-Methoxyphenyl)-4-(3,4,5-trimethoxyphenyl)furan 在 三氯化磷 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 5-[(2E)-2-[[3-(4-methoxyphenyl)-4-(3,4,5-trimethoxyphenyl)furan-2-yl]methylidene]hydrazinyl]-5-oxopentanoic acid
  参考文献：
  名称：

  Synthesis and Cytotoxic Evaluation of Combretafurans, Potential Scaffolds for Dual-Action Antitumoral Agents

  摘要：

  We have synthesized rigid analogues of combretastatin bearing a furan ring in place of the olefinic bridge. These compounds are cytotoxic at nanomolar concentrations in neuroblastoma cells, display a similar structure- activity relationship compared to combretastatin A4, and inhibit tubulin polymerization. We also show that the furan ring can be further functionalized. Thus, it is possible that combretafurans could act as scaffolds for the development of dual-action antitumoral agents.

  DOI：

  10.1021/jm060621o
• 作为产物：
  描述：

  3,4,5-三甲氧基苯乙酸 在 氢氧化钾 、 18-冠醚-6 、 TEA 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 7.5h， 生成 3-(4-Methoxyphenyl)-4-(3,4,5-trimethoxyphenyl)furan
  参考文献：
  名称：

  Synthesis and Cytotoxic Evaluation of Combretafurans, Potential Scaffolds for Dual-Action Antitumoral Agents

  摘要：

  We have synthesized rigid analogues of combretastatin bearing a furan ring in place of the olefinic bridge. These compounds are cytotoxic at nanomolar concentrations in neuroblastoma cells, display a similar structure- activity relationship compared to combretastatin A4, and inhibit tubulin polymerization. We also show that the furan ring can be further functionalized. Thus, it is possible that combretafurans could act as scaffolds for the development of dual-action antitumoral agents.

  DOI：

  10.1021/jm060621o

文献信息

• Photostability and Antiproliferative Activity of Furan Analogues of Combretastatin A-4
  作者：Alexander Scherbakov、Alexey V. Zakharov、Ekaterina I. Mikhaevich、Diana I. Salnikova、Anton V. Yadykov、Arina A. Kozhevnikova、Valerii Z. Shirinian

  DOI：10.1021/acs.chemrestox.2c00204

  日期：2022.11.21

  Cancer is one of the most serious health problems that usually require heavy medical treatment. It is important to ensure that no additional burden is placed on patients due to the modes of administration and/or poor quality of pharmaceuticals. In this regard, understanding, quantifying, and improving the photostability (resistance to UV light or sunlight) of drugs is among the important elements that can improve the patient’s quality of life. In this work, the photochemical properties of a wide range of furanone analogues of combretastatin A-4 and their antiproliferative activity against A-431 epidermoid carcinoma cells were studied in a search for compounds with improved photostability and antiproliferative activity. It was found that the incorporation of an arylidene moiety led to a significant improvement in photostability, while the antiproliferative activity strongly depends on the nature of the aryl residue in the arylidene moiety. The high photostability of arylidenes was achieved due to the delocalization of the central double bond of the 1,3,5-hexatriene system, which limited the 6π-electrocyclization. The best results in terms of antiproliferative activity were obtained for thiophene arylidene (IC50 = 0.6 μM) and 3,4-diarylfuran (IC50 = 0.047 μM). The obtained results address the lack of data available now in scientific literature on the photodegradation of combretastatin A-4 analogues and should be taken into account in studies of the side effects of pharmaceuticals based on them.

  癌症是最严重的健康问题之一，通常需要大量的药物治疗。必须确保不因给药方式和/或药品质量差而给患者造成额外负担。在这方面，了解、量化和改善药物的光稳定性（对紫外线或阳光的耐受性）是提高患者生活质量的重要因素之一。在这项工作中，为了寻找具有更好光稳定性和抗增殖活性的化合物，研究了多种康瑞他汀 A-4 呋喃酮类似物的光化学特性及其对 A-431 表皮样癌细胞的抗增殖活性。研究发现，加入亚芳基后，光稳定性显著提高，而抗增殖活性则在很大程度上取决于亚芳基中芳基残基的性质。1,3,5-己三烯体系中心双键的去局域化限制了 6π 电环化，从而使芳基烯具有较高的光稳定性。在抗增殖活性方面，噻吩亚芳基（IC50 = 0.6 μM）和 3,4-二芳基呋喃（IC50 = 0.047 μM）的结果最好。这些结果解决了目前科学文献中缺乏有关考布他丁 A-4 类似物光降解数据的问题，在研究基于这些类似物的药物的副作用时应加以考虑。