ethyl 5-(4-fluorophenylsulfonamido)-3-methylbenzofuran-2-carboxylate | 1333205-74-5

• 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: ethyl 5-(4-fluorophenylsulfonamido)-3-methylbenzofuran-2-carboxylate
• 英文别名: Ethyl 5-[(4-fluorophenyl)sulfonylamino]-3-methyl-1-benzofuran-2-carboxylate
• CAS: 1333205-74-5
• 化学式: C₁₈H₁₆FNO₅S
• 分子量: 377.393
• InChiKey: POBUBELEYZJVMY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  94
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl 5-(4-fluorophenylsulfonamido)-3-methylbenzofuran-2-carboxylate 在 potassium carbonate 、 potassium iodide 、 sodium hydroxide 作用下， 以 乙醇 、 丙酮 为溶剂， 生成 5-(N-benzyl-4-fluorophenylsulfonamido)-3-methylbenzofuran-2-carboxylic acid
  参考文献：
  名称：

  Discovery and optimization of new benzofuran derivatives against p53-independent malignant cancer cells through inhibition of HIF-1 pathway

  摘要：

  p53-independent malignant cancer is still severe health problem of human beings. HIF-1 pathway is believed to play an important role in the survival and developing progress of such cancers. In the present study, with the aim to inhibit the proliferation of p53-independent malignant cells, we disclose the optimization of 6a, the starting compound which is discovered in the screening of in-house compound collection. The structure-activity relationship (SAR) is summarized. The most potent derivative 8d, inhibits the proliferation of both p53-null and p53-mutated cells through inhibition of HIF-1 pathway. Our findings here provide a new chemotype in designing potent anticancer agent especially against those p53-independent malignant tumors. (C) 2016 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2016.03.112
• 作为产物：
  描述：

  4'-甲氧基乙酰苯胺 在 吡啶 、 盐酸 、 aluminum (III) chloride 、 乙醇 、 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 11.17h， 生成 ethyl 5-(4-fluorophenylsulfonamido)-3-methylbenzofuran-2-carboxylate
  参考文献：
  名称：

  新型苯并呋喃磺酰胺衍生物的合成，抗增殖活性及体外生物学评价

  摘要：

  在基于细胞的新型抗增殖剂筛选中，带有苯并呋喃磺酰胺支架的命中化合物1a对一组肿瘤细胞系表现出广谱抗增殖活性。有前景的1a体外抗增殖活性和结构新颖性促使我们研究1a的5种类似物的合成并测试其抗增殖活性。最有效的类似物1h与亲本1a相比具有增强的抗增殖活性，对NCI-H460细胞的IC 50值为4.13μM，而阳性对照为顺铂4.52μM。流式细胞仪分析显示1h在低微摩尔浓度下体外诱导NCI-H460细胞中显着水平的细胞凋亡。这些结果表明1a及其基于其苯并呋喃磺酰胺支架的类似物可能构成一类新型的抗增殖剂，值得进一步研究。

  DOI：

  10.1016/j.bmcl.2011.07.007

文献信息

• Synthesis, antiproliferative activities and in vitro biological evaluation of novel benzofuransulfonamide derivatives
  作者：Li Yang、Hua Lei、Cheng-Gen Mi、Huan Liu、Tian Zhou、Ying-Lan Zhao、Xiao-Yun Lai、Zi-Cheng Li、Hang Song、Wen-Cai Huang

  DOI：10.1016/j.bmcl.2011.07.007

  日期：2011.9

  exhibited broad-spectrum antiproliferative activities against a panel of tumor cell lines. The promising in vitro antiproliferative activity and structural novelty of 1a prompted us to investigate the synthesis of five analogs of 1a and test their antiproliferative activities. The most potent analogue, 1h, exhibited enhanced antiproliferative activities compared with the parent 1a, and exhibited an

  在基于细胞的新型抗增殖剂筛选中，带有苯并呋喃磺酰胺支架的命中化合物1a对一组肿瘤细胞系表现出广谱抗增殖活性。有前景的1a体外抗增殖活性和结构新颖性促使我们研究1a的5种类似物的合成并测试其抗增殖活性。最有效的类似物1h与亲本1a相比具有增强的抗增殖活性，对NCI-H460细胞的IC 50值为4.13μM，而阳性对照为顺铂4.52μM。流式细胞仪分析显示1h在低微摩尔浓度下体外诱导NCI-H460细胞中显着水平的细胞凋亡。这些结果表明1a及其基于其苯并呋喃磺酰胺支架的类似物可能构成一类新型的抗增殖剂，值得进一步研究。
• Discovery and optimization of new benzofuran derivatives against p53-independent malignant cancer cells through inhibition of HIF-1 pathway
  作者：Ying-Rui Yang、Jin-Lian Wei、Xiao-Fei Mo、Zhen-Wei Yuan、Jia-Lin Wang、Chao Zhang、Yi-Yue Xie、Qi-Dong You、Hao-Peng Sun

  DOI：10.1016/j.bmcl.2016.03.112

  日期：2016.6

  p53-independent malignant cancer is still severe health problem of human beings. HIF-1 pathway is believed to play an important role in the survival and developing progress of such cancers. In the present study, with the aim to inhibit the proliferation of p53-independent malignant cells, we disclose the optimization of 6a, the starting compound which is discovered in the screening of in-house compound collection. The structure-activity relationship (SAR) is summarized. The most potent derivative 8d, inhibits the proliferation of both p53-null and p53-mutated cells through inhibition of HIF-1 pathway. Our findings here provide a new chemotype in designing potent anticancer agent especially against those p53-independent malignant tumors. (C) 2016 Published by Elsevier Ltd.