tert-butyl N-[4-[[3-(6-methoxypyridin-3-yl)-5-(4-methylsulfonylphenyl)pyridin-2-yl]amino]butyl]carbamate | 1476713-83-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: tert-butyl N-[4-[[3-(6-methoxypyridin-3-yl)-5-(4-methylsulfonylphenyl)pyridin-2-yl]amino]butyl]carbamate
• CAS: 1476713-83-3
• 化学式: C₂₇H₃₄N₄O₅S
• 分子量: 526.657
• InChiKey: YQXXQFAUXSFKNV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  37
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  128
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[4-[[3-(6-methoxypyridin-3-yl)-5-(4-methylsulfonylphenyl)pyridin-2-yl]amino]butyl]carbamate 在 三氟乙酸 作用下， 以 二氯甲烷 、 甲醇 为溶剂， 反应 3.0h， 以89.8%的产率得到N-(6'-Methoxy-5-(4-(methylsulfonyl)phenyl)-3,3'-bipyridin-2-yl)butane-1,4-diamine
  参考文献：
  名称：

  Structure–Activity-Relationship Studies around the 2-Amino Group and Pyridine Core of Antimalarial 3,5-Diarylaminopyridines Lead to a Novel Series of Pyrazine Analogues with Oral in Vivo Activity

  摘要：

  Replacement of the pyridine core of antimalarial 3,5-diaryl-2-aminopyridines led to the identification of a novel series of pyrazine analogues with potent oral antimalarial activity. However, other changes to the pyridine core and replacement or substitution of the 2-amino group led to loss of antimalarial activity. The 3,5-diaryl-2-arninopyrazine series showed impressive in vitro antiplasmodial activity against the K1 (multidrug resistant) and NF54 (sensitive) strains of Plasmodium falciparum in the nanomolar IC50 range of 6-94 nM while also demonstrating good in vitro metabolic stability in human liver microsomes. In the Plasmodium berghei mouse model, this series generally exhibited good efficacy at low oral doses. One of the frontrunner compounds, 4, displayed potent in vitro antiplasmodial activity with IC50 values of 8.4 and 10 nM against the K1 and NF54 strains, respectively. When evaluated in P. berghei-infected mice, compound 4 was completely curative at an oral dose of 4 x 10 mg/kg.

  DOI：

  10.1021/jm401278d
• 作为产物：
  描述：

  N-1-(pyrid-2-yl)butane-1,4-diamine 在 bis-triphenylphosphine-palladium(II) chloride 、 N-溴代丁二酰亚胺(NBS) 、 potassium carbonate 、 三乙胺 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 为溶剂， 反应 49.0h， 生成 tert-butyl N-[4-[[3-(6-methoxypyridin-3-yl)-5-(4-methylsulfonylphenyl)pyridin-2-yl]amino]butyl]carbamate
  参考文献：
  名称：

  Structure–Activity-Relationship Studies around the 2-Amino Group and Pyridine Core of Antimalarial 3,5-Diarylaminopyridines Lead to a Novel Series of Pyrazine Analogues with Oral in Vivo Activity

  摘要：

  Replacement of the pyridine core of antimalarial 3,5-diaryl-2-aminopyridines led to the identification of a novel series of pyrazine analogues with potent oral antimalarial activity. However, other changes to the pyridine core and replacement or substitution of the 2-amino group led to loss of antimalarial activity. The 3,5-diaryl-2-arninopyrazine series showed impressive in vitro antiplasmodial activity against the K1 (multidrug resistant) and NF54 (sensitive) strains of Plasmodium falciparum in the nanomolar IC50 range of 6-94 nM while also demonstrating good in vitro metabolic stability in human liver microsomes. In the Plasmodium berghei mouse model, this series generally exhibited good efficacy at low oral doses. One of the frontrunner compounds, 4, displayed potent in vitro antiplasmodial activity with IC50 values of 8.4 and 10 nM against the K1 and NF54 strains, respectively. When evaluated in P. berghei-infected mice, compound 4 was completely curative at an oral dose of 4 x 10 mg/kg.

  DOI：

  10.1021/jm401278d