N-(3-(1H-imidazol-1-yl)propyl)-3-nitrobenzamide

• 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: N-(3-(1H-imidazol-1-yl)propyl)-3-nitrobenzamide
• 英文别名: N-[3-(1H-imidazol-1-yl)propyl]-3-nitrobenzamide；N-(3-imidazol-1-ylpropyl)-3-nitrobenzamide
• 化学式: C₁₃H₁₄N₄O₃
• mdl: MFCD00978405
• 分子量: 274.279
• InChiKey: BOENZJLHLMXPPE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  92.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(3-(1H-imidazol-1-yl)propyl)-3-nitrobenzamide 在 5%-palladium/activated carbon 、 氢气 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 生成 (E)-3-[3-(4-adamantan-1-yl-phenoxy)-acryloylamino]-N-(3-imidazole-1-yl-propyl)-benzamide
  参考文献：
  名称：

  Synthesis and Structure–Activity Relationship of (E)-Phenoxyacrylic Amide Derivatives as Hypoxia-Inducible Factor (HIF) 1α Inhibitors

  摘要：

  A series of (E)-phenoxyacrylic amide derivatives were synthesized and evaluated as hypoxia inducible factor (HIF) la inhibitors. The present structure activity relationship study on this series identified the morpholinoethyl containing ester 4p as a potent inhibitor of HIF-1 alpha under hypoxic conditions (IC50 = 0.12 mu M in a cell-based HRE reporter assay) in HCT116 cells. The representative compound 4p suppressed hypoxia-induced HIF-1 alpha accumulation and targeted gene expression in a dose-dependent manner. The effect of HIF-l alpha inhibition by 4p was further demonstrated by its inhibitory activity on in vitro tube formation and migration of cells, which may be valuable for development of novel therapeutics for cancer and tumor angiogenesis.

  DOI：

  10.1021/jm301419d
• 作为产物：
  描述：

  1-(3-氨基丙基)咪唑 、 间硝基苯甲酸 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 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以18%的产率得到N-(3-(1H-imidazol-1-yl)propyl)-3-nitrobenzamide
  参考文献：
  名称：

  Synthesis and Structure–Activity Relationship of (E)-Phenoxyacrylic Amide Derivatives as Hypoxia-Inducible Factor (HIF) 1α Inhibitors

  摘要：

  A series of (E)-phenoxyacrylic amide derivatives were synthesized and evaluated as hypoxia inducible factor (HIF) la inhibitors. The present structure activity relationship study on this series identified the morpholinoethyl containing ester 4p as a potent inhibitor of HIF-1 alpha under hypoxic conditions (IC50 = 0.12 mu M in a cell-based HRE reporter assay) in HCT116 cells. The representative compound 4p suppressed hypoxia-induced HIF-1 alpha accumulation and targeted gene expression in a dose-dependent manner. The effect of HIF-l alpha inhibition by 4p was further demonstrated by its inhibitory activity on in vitro tube formation and migration of cells, which may be valuable for development of novel therapeutics for cancer and tumor angiogenesis.

  DOI：

  10.1021/jm301419d

文献信息

• N-[2-4-(1H-Imidazol-1-yl)alkyl]-arylamides and pharmaceutical
  申请人：American Cyanamid Company

  公开号：US04568687A1

  公开（公告）日：1986-02-04

  This disclosure describes novel N-[.omega.-(1H-imidazol-1-yl)alkyl]arylamides which possess the property of inhibiting the enzyme thromboxane synthetase and are also useful in the treatment of hypertension and myocardial ischemia.

  这份披露描述了一种新颖的N-[.omega.-(1H-咪唑-1-基)烷基]芳基酰胺，具有抑制血栓素合酶酶活性的特性，并且在治疗高血压和心肌缺血方面也很有用。
• N-(2-4-(1H-imidazol-1-yl)alkyl)arylamides
  申请人：AMERICAN CYANAMID COMPANY

  公开号：EP0117462A2

  公开（公告）日：1984-09-05

  This disclosure describes novel N-[ω-(1H-imidazol-1-yl)alkyl]arylamides which possess the property of inhibiting the enzyme thromboxane synthetase and are also useful in the treatment of hypertension and myocardial ischemia.

  本公开介绍了新型 N-[ω-(1H-咪唑-1-基)烷基]芳基酰胺，它们具有抑制血栓素合成酶的特性，还可用于治疗高血压和心肌缺血。
• WRIGHT, W. B. ,, JR.;PRESS, J. B.
  作者：WRIGHT, W. B. ,, JR.、PRESS, J. B.

  DOI：——

  日期：——
• US4568687A
  申请人：——

  公开号：US4568687A

  公开（公告）日：1986-02-04
• Synthesis and Structure–Activity Relationship of (<i>E</i>)-Phenoxyacrylic Amide Derivatives as Hypoxia-Inducible Factor (HIF) 1α Inhibitors
  作者：Ravi Naik、Misun Won、Bo-Kyung Kim、Yan Xia、Hyun Kyung Choi、Guanghai Jin、Youngjin Jung、Hwan Mook Kim、Kyeong Lee

  DOI：10.1021/jm301419d

  日期：2012.12.13

  A series of (E)-phenoxyacrylic amide derivatives were synthesized and evaluated as hypoxia inducible factor (HIF) la inhibitors. The present structure activity relationship study on this series identified the morpholinoethyl containing ester 4p as a potent inhibitor of HIF-1 alpha under hypoxic conditions (IC50 = 0.12 mu M in a cell-based HRE reporter assay) in HCT116 cells. The representative compound 4p suppressed hypoxia-induced HIF-1 alpha accumulation and targeted gene expression in a dose-dependent manner. The effect of HIF-l alpha inhibition by 4p was further demonstrated by its inhibitory activity on in vitro tube formation and migration of cells, which may be valuable for development of novel therapeutics for cancer and tumor angiogenesis.