2-[[4-(Tert-butoxycarbonyl)amino-1-butyl]amino]pyridine | 258881-19-5

• 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: 2-[[4-(Tert-butoxycarbonyl)amino-1-butyl]amino]pyridine
• 英文别名: tert-butyl N-[4-(pyridin-2-ylamino)butyl]carbamate
• CAS: 258881-19-5
• 化学式: C₁₄H₂₃N₃O₂
• 分子量: 265.356
• InChiKey: ZZXFWOJLSNURLJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  63.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[[4-(Tert-butoxycarbonyl)amino-1-butyl]amino]pyridine 在 bis-triphenylphosphine-palladium(II) chloride 、 N-溴代丁二酰亚胺(NBS) 、 potassium carbonate 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 36.0h， 生成 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：

  2-碘吡啶 在 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 32.0h， 生成 2-[[4-(Tert-butoxycarbonyl)amino-1-butyl]amino]pyridine
  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

文献信息

• Vitronectin receptor antagonists
  申请人：SmithKline Beecham Corporation

  公开号：US06458814B1

  公开（公告）日：2002-10-01

  Compounds of the formula (I) are disclosed which are vitronectin receptor antagonists and are useful in the treatment of osteoporosis: or a pharmaceutically acceptable salt thereof.

  公式（I）的化合物被揭示为玻璃蛋白受体拮抗剂，并且在骨质疏松症的治疗中有用：或其药学上可接受的盐。
• EP1102587A4
  申请人：——

  公开号：EP1102587A4

  公开（公告）日：2003-03-12
• VITRONECTIN RECEPTOR ANTAGONISTS
  申请人：SMITHKLINE BEECHAM CORPORATION

  公开号：EP1102587A2

  公开（公告）日：2001-05-30
• US6458814B1
  申请人：——

  公开号：US6458814B1

  公开（公告）日：2002-10-01
• [EN] VITRONECTIN RECEPTOR ANTAGONISTS<br/>[FR] ANTAGONISTES DU RECEPTEUR DE LA PROTEINE S
  申请人：SMITHKLINE BEECHAM CORP

  公开号：WO2000007544A2

  公开（公告）日：2000-02-17

  Compounds of formula (I) are disclosed which are vitronectin receptor antagonists and are useful in the treatment of osteoporosis; or a pharmaceutically acceptable salt thereof.