5-(4-bromo-N-(4-bromobenzyl)phenylsulfonamido)-3-methylbenzofuran-2-carboxylic acid

• 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: 5-(4-bromo-N-(4-bromobenzyl)phenylsulfonamido)-3-methylbenzofuran-2-carboxylic acid
• 英文别名: 5-[(4-Bromophenyl)methyl-(4-bromophenyl)sulfonylamino]-3-methyl-1-benzofuran-2-carboxylic acid；5-[(4-bromophenyl)methyl-(4-bromophenyl)sulfonylamino]-3-methyl-1-benzofuran-2-carboxylic acid
• 化学式: C₂₃H₁₇Br₂NO₅S
• 分子量: 579.266
• InChiKey: CQRIIHLYYBUQDX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  96.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-(4-bromo-N-(4-bromobenzyl)phenylsulfonamido)-3-methylbenzofuran-2-carboxylic acid 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 4-bromo-N-(4-bromobenzyl)-N-(3-methyl-2-(piperazine-1-carbonyl)benzofuran-5-yl)benzenesulfonamide
  参考文献：
  名称：

  Design, synthesis, and evaluation of benzofuran derivatives as novel anti-pancreatic carcinoma agents via interfering the hypoxia environment by targeting HIF-1α pathway

  摘要：

  Pancreatic ductal adenocarcinoma (PDAC) is one of the most common type of pancreatic cancer, and has still been the medicinal mystery. New drugs and treatment strategies are urgently needed. In this study, 32 benzofuran derivatives are designed, synthesized and evaluated as potential agents against the pancreatic cancer. Among them, compound 9o with the best physicochemical and pharmacokinetic properties exhibited excellent cytotoxicity against many tumor cell lines. In vivo study showed that compound 9o dramatically suppressed the tumor growth of nude mice. Furthermore, compound 9o could affect the hypoxia environment through Hif-1 alpha/VEGF pathway, resulting in the anti-angiogenic activity. These studies indicated that compound 9o was a promising candidate for the treatment of PDAC, deserving further studies. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.05.042
• 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 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 26.62h， 生成 5-(4-bromo-N-(4-bromobenzyl)phenylsulfonamido)-3-methylbenzofuran-2-carboxylic acid
  参考文献：
  名称：

  Design, synthesis, and evaluation of benzofuran derivatives as novel anti-pancreatic carcinoma agents via interfering the hypoxia environment by targeting HIF-1α pathway

  摘要：

  Pancreatic ductal adenocarcinoma (PDAC) is one of the most common type of pancreatic cancer, and has still been the medicinal mystery. New drugs and treatment strategies are urgently needed. In this study, 32 benzofuran derivatives are designed, synthesized and evaluated as potential agents against the pancreatic cancer. Among them, compound 9o with the best physicochemical and pharmacokinetic properties exhibited excellent cytotoxicity against many tumor cell lines. In vivo study showed that compound 9o dramatically suppressed the tumor growth of nude mice. Furthermore, compound 9o could affect the hypoxia environment through Hif-1 alpha/VEGF pathway, resulting in the anti-angiogenic activity. These studies indicated that compound 9o was a promising candidate for the treatment of PDAC, deserving further studies. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.05.042

文献信息

• 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.