2',3'-di-O-(t-butyldimethylsilyl)-N⁶-benzoylneplanocin A 6'-aldehyde | 400611-64-5

• 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'-di-O-(t-butyldimethylsilyl)-N⁶-benzoylneplanocin A 6'-aldehyde
• 英文别名: N-[9-[(1R,4R,5S)-4,5-bis[[tert-butyl(dimethyl)silyl]oxy]-3-formylcyclopent-2-en-1-yl]purin-6-yl]benzamide
• CAS: 400611-64-5
• 化学式: C₃₀H₄₃N₅O₄Si₂
• 分子量: 593.874
• InChiKey: MDEUXTXPWPRCKD-GPXOXTDOSA-N

物化性质

• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.54
• 重原子数：
  41
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2',3'-di-O-(t-butyldimethylsilyl)-N⁶-benzoylneplanocin A 6'-aldehyde 在 氟化铵 、 偶氮二甲酸二异丙酯 、 trichloromethyl-Titanium 、 氨 、 氯乙酸 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 21.33h， 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 在 咪唑 、 barium permanganate 、 溶剂黄146 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 45.0h， 生成 2',3'-di-O-(t-butyldimethylsilyl)-N⁶-benzoylneplanocin A 6'-aldehyde
  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

文献信息

• New Neplanocin Analogues. 12. Alternative Synthesis and Antimalarial Effect of (6‘<i>R</i>)-6‘-<i>C</i>-Methylneplanocin A, a Potent AdoHcy Hydrolase Inhibitor
  作者：Satoshi Shuto、Noriaki Minakawa、Satoshi Niizuma、Hye-Sook Kim、Yusuke Wataya、Akira Matsuda

  DOI：10.1021/jm010374i

  日期：2002.1.1

  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).