2-(allyloxy)-N-((2R,3R)-3-((tert-butyldimethylsilyl)oxy)-4-(4-fluoro-N-methylphenylsulfonamido)-2-methylbutyl)-N-((2S)-1-((4-methoxybenzyl)oxy)propan-2-yl)-5-nitrobenzamide | 1403480-47-6

• 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: 2-(allyloxy)-N-((2R,3R)-3-((tert-butyldimethylsilyl)oxy)-4-(4-fluoro-N-methylphenylsulfonamido)-2-methylbutyl)-N-((2S)-1-((4-methoxybenzyl)oxy)propan-2-yl)-5-nitrobenzamide
• 英文别名: 2-(allyloxy)-N-((2R,3R)-3-((tert-butyldimethylsilyl)oxy)-4-(4-fluoro-N-methylphenylsulfonamido)-2-methylbutyl)-N-((S)-1-((4-methoxybenzyl)oxy)propan-2-yl)-5-nitrobenzamide
• CAS: 1403480-47-6
• 化学式: C₃₉H₅₄FN₃O₉SSi
• 分子量: 788.022
• InChiKey: BOFYCXGVCGRSTP-NSKVNMAASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  54.0
• 可旋转键数：
  20.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  137.75
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  2-(allyloxy)-N-((2R,3R)-3-((tert-butyldimethylsilyl)oxy)-4-(4-fluoro-N-methylphenylsulfonamido)-2-methylbutyl)-N-((2S)-1-((4-methoxybenzyl)oxy)propan-2-yl)-5-nitrobenzamide 在 Grubbs catalyst first generation 、 tin(II) chloride dihdyrate 、 palladium 10% on activated carbon 、 四丁基氟化铵 、 sodium hydride 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 211.08h， 生成 N-(((7R,8R)-13-(3-(3,5-dimethylisoxazol-4-yl)ureido)-10-((2S)-1-hydroxypropan-2-yl)-8-methyl-11-oxo-3,4,5,7,8,9,10,11-octahydro-2H-benzo[b][1,9,5]dioxaazacyclotridecin-7-yl)methyl)-4-fluoro-N-methylbenzenesulfonamide
  参考文献：
  名称：

  Diversity-Oriented Synthesis-Facilitated Medicinal Chemistry: Toward the Development of Novel Antimalarial Agents

  摘要：

  Here, we describe medicinal chemistry that was accelerated by a diversity-oriented synthesis (DOS) pathway, and in vivo studies of our previously reported macrocyclic antimalarial agent that derived from the synthetic pathway. Structure-activity relationships that focused on both appendage and skeletal features yielded a nanomolar inhibitor of P. falciparum asexual blood-stage growth with improved solubility and microsomal stability and reduced hERG binding. The build/couple/pair (B/C/P) synthetic strategy, used in the preparation of the original screening library, facilitated medicinal chemistry optimization of the antimalarial lead.

  DOI：

  10.1021/jm500994n
• 作为产物：
  描述：

  N-((2R,3R)-2-((tert-butyldimethylsilyl)oxy)-4-(((2S)-1-((4-methoxybenzyl)oxy)propan-2-yl)amino)-3-methylbutyl)-4-fluoro-N-methylbenzenesulfonamide 在 双(2-氧代-3-恶唑烷基)次磷酰氯 、 sodium hydride 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 17.16h， 生成 2-(allyloxy)-N-((2R,3R)-3-((tert-butyldimethylsilyl)oxy)-4-(4-fluoro-N-methylphenylsulfonamido)-2-methylbutyl)-N-((2S)-1-((4-methoxybenzyl)oxy)propan-2-yl)-5-nitrobenzamide
  参考文献：
  名称：

  Diversity-Oriented Synthesis-Facilitated Medicinal Chemistry: Toward the Development of Novel Antimalarial Agents

  摘要：

  Here, we describe medicinal chemistry that was accelerated by a diversity-oriented synthesis (DOS) pathway, and in vivo studies of our previously reported macrocyclic antimalarial agent that derived from the synthetic pathway. Structure-activity relationships that focused on both appendage and skeletal features yielded a nanomolar inhibitor of P. falciparum asexual blood-stage growth with improved solubility and microsomal stability and reduced hERG binding. The build/couple/pair (B/C/P) synthetic strategy, used in the preparation of the original screening library, facilitated medicinal chemistry optimization of the antimalarial lead.

  DOI：

  10.1021/jm500994n