ethyl 5-((2-bromophenyl)sulfonamido)-3-methylbenzofuran-2-carboxylate

• 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-((2-bromophenyl)sulfonamido)-3-methylbenzofuran-2-carboxylate
• 英文别名: Ethyl 5-[(2-bromophenyl)sulfonylamino]-3-methyl-1-benzofuran-2-carboxylate；ethyl 5-[(2-bromophenyl)sulfonylamino]-3-methyl-1-benzofuran-2-carboxylate
• 化学式: C₁₈H₁₆BrNO₅S
• 分子量: 438.299
• InChiKey: ARVJKUUIGXBHNL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 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：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 5-((2-bromophenyl)sulfonamido)-3-methylbenzofuran-2-carboxylate 、 alkaline earth salt of/the/ methylsulfuric acid 在 potassium carbonate 、 potassium iodide 作用下， 以 丙酮 为溶剂， 以52.4%的产率得到ethyl 5-((N-benzyl-2-bromophenyl)sulfonamido)-3-methylbenzofuran-2-carboxylate
  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 、 potassium carbonate 、 potassium iodide 作用下， 以 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 34.12h， 生成 ethyl 5-((2-bromophenyl)sulfonamido)-3-methylbenzofuran-2-carboxylate
  参考文献：
  名称：

  具有新型抗血管生成潜力的新型HIF-1抑制剂N-（苯并呋喃-5-基）芳族磺酰胺衍生物的合成与评价。

  摘要：

  缺氧诱导因子-1（HIF-1）作为肿瘤转移，血管生成和患者预后不良的关键介质，已被认为是重要的抗癌药物。合成了一系列新的N-（苯并呋喃-5-基）芳族磺酰胺衍生物，并将其评估为HIF-1抑制剂。在这些化合物中，7q通过在缺氧条件下下调HIF-1α的表达对HIF-1表现出特异性抑制作用。它抑制了MCF-7细胞中HIF-1的转录活性（IC50 = 12.5±0.7μM）和VEGF的分泌（IC50 =18.8μM）。同时，它还以无毒浓度显着抑制了缺氧诱导的HUVEC细胞迁移。另外，管形成试验证明了其抗血管生成活性。最后，体内研究表明化合物7q可以延缓CAM模型中的血管生成。

  DOI：

  10.1016/j.bmc.2016.06.021

文献信息

• Synthesis and evaluation of N -(benzofuran-5-yl)aromaticsulfonamide derivatives as novel HIF-1 inhibitors that possess anti-angiogenic potential
  作者：Jinlian Wei、Yingrui Yang、Yali Li、Xiaofei Mo、Xiaoke Guo、Xiaojin Zhang、Xiaoli Xu、Zhengyu Jiang、Qidong You

  DOI：10.1016/j.bmc.2016.06.021

  日期：2017.3

  (HIF-1) as a key mediator in tumor metastasis, angiogenesis, and poor patient prognosis has been recognized as an important cancer drug target. A novel series of N-(benzofuran-5-yl)aromaticsulfonamide derivatives were synthesized and evaluated as HIF-1 inhibitor. Among these compounds, 7q exhibited specific inhibitory effects on HIF-1 by downregulating the expression of HIF-1α under hypoxic conditions

  缺氧诱导因子-1（HIF-1）作为肿瘤转移，血管生成和患者预后不良的关键介质，已被认为是重要的抗癌药物。合成了一系列新的N-（苯并呋喃-5-基）芳族磺酰胺衍生物，并将其评估为HIF-1抑制剂。在这些化合物中，7q通过在缺氧条件下下调HIF-1α的表达对HIF-1表现出特异性抑制作用。它抑制了MCF-7细胞中HIF-1的转录活性（IC50 = 12.5±0.7μM）和VEGF的分泌（IC50 =18.8μM）。同时，它还以无毒浓度显着抑制了缺氧诱导的HUVEC细胞迁移。另外，管形成试验证明了其抗血管生成活性。最后，体内研究表明化合物7q可以延缓CAM模型中的血管生成。
• 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.