N1,N2-dimethyl-N1-(pyridin-3-ylmethyl)ethane-1,2-diamine

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N1,N2-dimethyl-N1-(pyridin-3-ylmethyl)ethane-1,2-diamine
• 英文别名: N,N'-dimethyl-N-(pyridin-3-ylmethyl)ethylenediamine；N,N'-dimethyl-N-(3-pyridylmethyl)ethylenediamine；N,N'-dimethyl-N'-(pyridin-3-ylmethyl)ethane-1,2-diamine
• 化学式: C₁₀H₁₇N₃
• 分子量: 179.265
• InChiKey: CFOPCTHLUORMKA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  28.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N1,N2-dimethyl-N1-(pyridin-3-ylmethyl)ethane-1,2-diamine 、 4-(chloromethyl)-N-(4-(trifluoromethyl)phenyl)benzamide 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以72.4%的产率得到4-((methyl(2-(methyl(pyridin-3-ylmethyl)amino)ethyl)amino)methyl)-N-(4-(trifluoromethyl)phenyl)benzamide
  参考文献：
  名称：

  Synthesis and structure–activity relationships of novel, potent, orally active hypoxia-inducible factor-1 inhibitors

  摘要：

  Hypoxia-inducible factor-1 (HIF-1) is the chief transcription factor regulating hypoxia-driven gene expression. HIF-1 overexpression is associated with poor prognosis in several cancers and therefore represents an attractive target for novel antitumor agents. We explored small molecule inhibitors of the HIF-1 pathway. Using high-throughput-screening, we identified benzanilide compound 1 (IC50=560 nM) as a seed. Subsequent extensive derivatization led to the discovery of compounds 43a and 51d, with anti-HIF-1 activities in vitro (IC50=21 and 0.47 nM, respectively), and in vivo. Additionally, 43a (12.5-100mg/kg) also displayed in vivo anti-tumor efficacy, without influencing body weight.

  DOI：

  10.1016/j.bmc.2014.07.020
• 作为产物：
  描述：

  3-(bromomethyl)pyridine hydrobromide 、 N,N'-二甲基乙二胺 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 以79.4%的产率得到N1,N2-dimethyl-N1-(pyridin-3-ylmethyl)ethane-1,2-diamine
  参考文献：
  名称：

  Synthesis and structure–activity relationships of novel, potent, orally active hypoxia-inducible factor-1 inhibitors

  摘要：

  Hypoxia-inducible factor-1 (HIF-1) is the chief transcription factor regulating hypoxia-driven gene expression. HIF-1 overexpression is associated with poor prognosis in several cancers and therefore represents an attractive target for novel antitumor agents. We explored small molecule inhibitors of the HIF-1 pathway. Using high-throughput-screening, we identified benzanilide compound 1 (IC50=560 nM) as a seed. Subsequent extensive derivatization led to the discovery of compounds 43a and 51d, with anti-HIF-1 activities in vitro (IC50=21 and 0.47 nM, respectively), and in vivo. Additionally, 43a (12.5-100mg/kg) also displayed in vivo anti-tumor efficacy, without influencing body weight.

  DOI：

  10.1016/j.bmc.2014.07.020

文献信息

• Substituted azetidiones as anti-inflammatory and antidegenerative agents
  申请人：Merck & Co., Inc.

  公开号：US05747485A1

  公开（公告）日：1998-05-05

  Substituted azetidinones are herein disclosed for use in the treatment of various elastase-mediated diseases.

  本文披露了用于治疗各种弹性蛋白酶介导疾病的取代氮杂四环酮。
• Substituted azetidinones as anti-inflammatory and antidegenerative agents
  申请人：Merck & Co., Inc.

  公开号：US05591737A1

  公开（公告）日：1997-01-07

  New substituted azetidinones of the general Formula (I) which have been found to be potent elastase inhibitors and thereby useful anti-inflammatory and antidegenerative agents are described. ##STR1## wherein R.sub.4 is (a) ##STR2## or (b) ##STR3## where R.sub.x is carboxy C.sub.1-6 alkyl, benzyloxycarbonylC.sub.1-3 alkyl, or t-butoxycarbonylC.sub.1-3 alkyl, wherein Q is a covalent bond or ##STR4## wherein R.sub.5 and R.sub.6 are each individually C.sub.1-3 alkyl or hydrogen, Y is ##STR5## or a covalent bond.

  本文描述了一般式（I）的新置换的氮杂环丙酮，这些化合物被发现具有强效的弹性蛋白酶抑制剂活性，因此可用作抗炎和抗退化药物。其中，R.sub.4是（a）##STR2##或（b）##STR3##，其中R.sub.x是羧基C.sub.1-6烷基，苄氧羰基C.sub.1-3烷基或叔丁氧羰基C.sub.1-3烷基，其中Q是共价键或##STR4##，其中R.sub.5和R.sub.6各自是C.sub.1-3烷基或氢，Y是##STR5##或共价键。
• New substituted azetidinones as anti-inflammatory and antidegenerative agents
  申请人：Merck & Co., Inc.

  公开号：EP0595557B1

  公开（公告）日：2004-06-30
• EP0755262A4
  申请人：——

  公开号：EP0755262A4

  公开（公告）日：1997-05-07
• COMPOSITION FOR THE TREATMENT OF LUNG DISEASE
  申请人：Merck & Co., Inc.

  公开号：EP0755262A1

  公开（公告）日：1997-01-29