N-((2,2-dimethyl-2,3-dihydrobenzofuran-5-yl)methyl)benzenamine | 947972-24-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 香豆素
• 英文名称: N-((2,2-dimethyl-2,3-dihydrobenzofuran-5-yl)methyl)benzenamine
• 英文别名: N-[(2,2-dimethyl-3H-1-benzofuran-5-yl)methyl]aniline
• CAS: 947972-24-9
• 化学式: C₁₇H₁₉NO
• 分子量: 253.344
• InChiKey: GSUKZMIINBBSHY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-((2,2-dimethyl-2,3-dihydrobenzofuran-5-yl)methyl)benzenamine 、 3,4-二甲氧基苯磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 以42%的产率得到N-((2,2-dimethyl-2,3-dihydrobenzofuran-5-yl)methyl)-3,4-dimethoxy-N-phenylbenzenesulfonamide
  参考文献：
  名称：

  [EN] INHIBITORS OF HIF AND ANGIOGENESIS
  [FR] INHIBITEURS DE HIF ET DE L'ANGIOGENÈSE

  摘要：

  公开号：

  WO2011133659A3
• 作为产物：
  描述：

  2,2-二甲基-2,3-二氢-1-苯并呋喃-5-甲醛 、 苯胺 在 sodium cyanoborohydride 、 zinc(II) chloride 作用下， 以 甲醇 为溶剂， 以84%的产率得到N-((2,2-dimethyl-2,3-dihydrobenzofuran-5-yl)methyl)benzenamine
  参考文献：
  名称：

  Design and Synthesis of Novel Small-Molecule Inhibitors of the Hypoxia Inducible Factor Pathway

  摘要：

  Hypoxia, a reduction in partial oxygen pressure, is a salient property of solid tumors. Hypoxia drives malignant progression and metastasis in tumors and participates in tumor resistance to radio- and chemotherapies. Hypoxia activates the hypoxia-inducible factor (HIF) family of transcription factors, which induce target genes that regulate adaptive biological processes such as anaerobic metabolism, cell motility, and angiogenesis. Clinical evidence has demonstrated that expression of HIF-1 is strongly associated with poor patient prognosis and activation of HIF-1 contributes to malignant behavior and therapeutic resistance. Consequently, HIF-1 has become an important therapeutic target for inhibition by small molecules. Herein, we describe the design and synthesis of small molecules that inhibit the HIF-1 signaling pathway. Many of these compounds exhibit inhibitory activity in the nanomolar range. Separate mechanistic studies indicate that these inhibitors do not alter HIF-1 levels but interfere with the ability of HIF-1 alpha/HIF-1 beta to interact with cofactors p300/CBP to form an active transcriptional complex.

  DOI：

  10.1021/jm201018g

文献信息

• [EN] INHIBITORS OF HIF AND ANGIOGENESIS<br/>[FR] INHIBITEURS DE HIF ET DE L'ANGIOGENÈSE
  申请人：UNIV EMORY

  公开号：WO2011133659A3

  公开（公告）日：2012-03-15
• Design and Synthesis of Novel Small-Molecule Inhibitors of the Hypoxia Inducible Factor Pathway
  作者：Suazette Reid Mooring、Hui Jin、Narra S. Devi、Adnan A. Jabbar、Stefan Kaluz、Yuan Liu、Erwin G. Van Meir、Binghe Wang

  DOI：10.1021/jm201018g

  日期：2011.12.22

  Hypoxia, a reduction in partial oxygen pressure, is a salient property of solid tumors. Hypoxia drives malignant progression and metastasis in tumors and participates in tumor resistance to radio- and chemotherapies. Hypoxia activates the hypoxia-inducible factor (HIF) family of transcription factors, which induce target genes that regulate adaptive biological processes such as anaerobic metabolism, cell motility, and angiogenesis. Clinical evidence has demonstrated that expression of HIF-1 is strongly associated with poor patient prognosis and activation of HIF-1 contributes to malignant behavior and therapeutic resistance. Consequently, HIF-1 has become an important therapeutic target for inhibition by small molecules. Herein, we describe the design and synthesis of small molecules that inhibit the HIF-1 signaling pathway. Many of these compounds exhibit inhibitory activity in the nanomolar range. Separate mechanistic studies indicate that these inhibitors do not alter HIF-1 levels but interfere with the ability of HIF-1 alpha/HIF-1 beta to interact with cofactors p300/CBP to form an active transcriptional complex.