2',3',6'-tri-O-(t-butyldimethylsilyl)-N⁶-benzoylneplanocin | 400611-62-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: 2',3',6'-tri-O-(t-butyldimethylsilyl)-N⁶-benzoylneplanocin
• 英文别名: N-[9-[(1R,4R,5S)-4,5-bis[[tert-butyl(dimethyl)silyl]oxy]-3-[[tert-butyl(dimethyl)silyl]oxymethyl]cyclopent-2-en-1-yl]purin-6-yl]benzamide
• CAS: 400611-62-3
• 化学式: C₃₆H₅₉N₅O₄Si₃
• 分子量: 710.152
• InChiKey: PWFSFFRSTQVEDA-NNFJYWIMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.36
• 重原子数：
  48
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  100
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2',3',6'-tri-O-(t-butyldimethylsilyl)-N⁶-benzoylneplanocin 在 氟化铵 、 barium permanganate 、 氨 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 50.5h， 生成 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 、 叔丁基二甲基氯硅烷 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 13.0h， 以100%的产率得到2',3',6'-tri-O-(t-butyldimethylsilyl)-N⁶-benzoylneplanocin
  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