(6'R)-2',3'-di-O-(tert-butyldimethylsilyl)-6'-methylnaplanocin A | 400611-68-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: (6'R)-2',3'-di-O-(tert-butyldimethylsilyl)-6'-methylnaplanocin A
• 英文别名: (1R)-1-[(3R,4S,5R)-3-(6-aminopurin-9-yl)-4,5-bis[[tert-butyl(dimethyl)silyl]oxy]cyclopenten-1-yl]ethanol
• CAS: 400611-68-9
• 化学式: C₂₄H₄₃N₅O₃Si₂
• 分子量: 505.808
• InChiKey: SFVJJTWAIUGKIM-QOJCHSLYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.05
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  108
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (6'R)-2',3'-di-O-(tert-butyldimethylsilyl)-6'-methylnaplanocin A 在 氟化铵 作用下， 以 甲醇 为溶剂， 反应 18.0h， 以74%的产率得到6'-(R)-methylneplanocin A
  参考文献：
  名称：

  New Neplanocin Analogues. 12. Alternative Synthesis and Antimalarial Effect of (6‘R)-6‘-C-Methylneplanocin A, a Potent AdoHcy Hydrolase Inhibitor

  摘要：

  An improved method for the synthesis of (6'R)-6'-C-methylneplanocin A (RMNPA, 2), a potent S-adenosyl-L-homocysteine (AdoHcy) hydrolase inhibitor, was developed via a chelation-controlled stereoselective addition of MeTiCl3 to the neplanocin A 6'-aldehyde derivative 6. Compound 2 effectively inhibited the growth of malaria parasites both in vitro and in vivo. The antimalarial EC50 value of 2 against Plasmodium berghei in mice was 1.0 mg/kg/day, which was superior to that of chloroquine (EC50 = 1.8 mg/kg/day).

  DOI：

  10.1021/jm010374i
• 作为产物：
  描述：

  N⁶-benzoyl-9-<(1R,2S,3R)-2,3-dihydroxy-4-(hydroxymethyl)-4-cyclopenten-1-yl>adenine 在 咪唑 、 barium permanganate 、 偶氮二甲酸二异丙酯 、 氨 、 溶剂黄146 、 氯乙酸 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.33h， 生成 (6'R)-2',3'-di-O-(tert-butyldimethylsilyl)-6'-methylnaplanocin A
  参考文献：
  名称：

  New Neplanocin Analogues. 12. Alternative Synthesis and Antimalarial Effect of (6‘R)-6‘-C-Methylneplanocin A, a Potent AdoHcy Hydrolase Inhibitor

  摘要：

  An improved method for the synthesis of (6'R)-6'-C-methylneplanocin A (RMNPA, 2), a potent S-adenosyl-L-homocysteine (AdoHcy) hydrolase inhibitor, was developed via a chelation-controlled stereoselective addition of MeTiCl3 to the neplanocin A 6'-aldehyde derivative 6. Compound 2 effectively inhibited the growth of malaria parasites both in vitro and in vivo. The antimalarial EC50 value of 2 against Plasmodium berghei in mice was 1.0 mg/kg/day, which was superior to that of chloroquine (EC50 = 1.8 mg/kg/day).

  DOI：

  10.1021/jm010374i