4-(bromomethyl)-N-cyclopentyl-N-((2,2-dimethyl-2H-chromen-6-yl)methyl)benzenesulfonamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 4-(bromomethyl)-N-cyclopentyl-N-((2,2-dimethyl-2H-chromen-6-yl)methyl)benzenesulfonamide
• 英文别名: 4-(bromomethyl)-N-cyclopentyl-N-[(2,2-dimethylchromen-6-yl)methyl]benzenesulfonamide
• 化学式: C₂₄H₂₈BrNO₃S
• 分子量: 490.461
• InChiKey: MBTAFBVZPOHEEZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-((2,2-dimethyl-2H-chromen-6-yl)methyl)cyclopentanamine 、 4-溴甲基苯磺酰氯 在 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 以57%的产率得到4-(bromomethyl)-N-cyclopentyl-N-((2,2-dimethyl-2H-chromen-6-yl)methyl)benzenesulfonamide
  参考文献：
  名称：

  Examining the structure-activity relationship of benzopyran-based inhibitors of the hypoxia inducible factor-1 pathway

  摘要：

  Many forms of solid tumor have a characteristic feature known as hypoxia, which describes a low or nonexistent presence of oxygen in the cellular microenvironment. This decrease in oxygen causes activation of the hypoxia inducible factor (HIF) pathway, which activates the transcription of many genes that cause cell proliferation, metastasis, increased glycolysis and angiogenesis. Increased HIF expression has been linked with poor patient prognosis, increased malignancy, and therapeutic resistance. Previous work in our lab has identified 1 and 2 as inhibitors of the HIF pathway, specifically as disrupters of the p300-HIF-1 alpha complex formation. A library of sulfonamide analogs has been designed and synthesized with the intent of examining the SAR of this series of compounds and improving potency and physicochemical properties as compared with lead compounds 1 and 2. At the end, we have achieved a thorough understanding of the structural features critical for future optimization work. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2017.02.073

文献信息

• Examining the structure-activity relationship of benzopyran-based inhibitors of the hypoxia inducible factor-1 pathway
  作者：Jalisa Ferguson、Zeus De Los Santos、Narra Devi、Erwin Van Meir、Sarah Zingales、Binghe Wang

  DOI：10.1016/j.bmcl.2017.02.073

  日期：2017.4

  Many forms of solid tumor have a characteristic feature known as hypoxia, which describes a low or nonexistent presence of oxygen in the cellular microenvironment. This decrease in oxygen causes activation of the hypoxia inducible factor (HIF) pathway, which activates the transcription of many genes that cause cell proliferation, metastasis, increased glycolysis and angiogenesis. Increased HIF expression has been linked with poor patient prognosis, increased malignancy, and therapeutic resistance. Previous work in our lab has identified 1 and 2 as inhibitors of the HIF pathway, specifically as disrupters of the p300-HIF-1 alpha complex formation. A library of sulfonamide analogs has been designed and synthesized with the intent of examining the SAR of this series of compounds and improving potency and physicochemical properties as compared with lead compounds 1 and 2. At the end, we have achieved a thorough understanding of the structural features critical for future optimization work. (C) 2017 Elsevier Ltd. All rights reserved.