N₆-benzoyl-9-<2(S)-hydroxy-1-<(methylsulfonyl)oxy>-3(R)-nonyl>adenine | 143707-20-4

• 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: N₆-benzoyl-9-<2(S)-hydroxy-1-<(methylsulfonyl)oxy>-3(R)-nonyl>adenine
• 英文别名: N₆-benzoyl-9-{2(S)-hydroxy-1-[(methylsulfonyl)oxy]-3(R)-nonyl}adenine；[(2R,3R)-3-(6-benzamidopurin-9-yl)-2-hydroxynonyl] methanesulfonate
• CAS: 143707-20-4
• 化学式: C₂₂H₂₉N₅O₅S
• 分子量: 475.569
• InChiKey: ZYZYRADNHXCENZ-MSOLQXFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  33
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  145
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N₆-benzoyl-9-<2(S)-hydroxy-1-<(methylsulfonyl)oxy>-3(R)-nonyl>adenine 以 苯 为溶剂， 反应 1.5h， 以95%的产率得到10-benzamido-5,6-dihydro-4(R)-hexyl-5(S)-hydroxy-4H-pyrimido<1,2,3-cd>purin-5-ium mesylate
  参考文献：
  名称：

  Adenosine deaminase inhibitors. Synthesis and biological evaluation of C1' and nor-C1' derivatives of (+)-erythro-9-[2(S)-hydroxy-3(R)-nonyl]adenine

  摘要：

  The synthesis of various chiral derivatives of (+)-erythro-9-(2-hydroxy-3-nonyl)adenine, (+)-EHNA, from (2S,3R)-3-amino-1,2-O-isopropylidene-1,2-nonanediol by condensation with 5-amino-4,6-dichloropyrimidine is described. The compounds synthesized were Cl'- and nor-Cl'-(+)-EHNA derivatives. When tested with calf spleen ADA, Cl'-OH- and nor-Cl'-(+)-EHNA had comparable inhibitory activity that was 1 order of magnitude lower than that of (+)-EHNA. Potency was reduced further in nor-Cl' derivatives.

  DOI：

  10.1021/jm00100a025
• 作为产物：
  描述：

  magnesium,pentane,chloride 在 吡啶 、 盐酸 、 lithium aluminium tetrahydride 、 sodium azide 、 dilithium tetrachlorocuprate 、 三正丁胺 、 氨 作用下， 以 乙醚 、 乙醇 、 二氯甲烷 、 戊醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 159.75h， 生成 N₆-benzoyl-9-<2(S)-hydroxy-1-<(methylsulfonyl)oxy>-3(R)-nonyl>adenine
  参考文献：
  名称：

  Adenosine deaminase inhibitors. Synthesis and biological evaluation of C1' and nor-C1' derivatives of (+)-erythro-9-[2(S)-hydroxy-3(R)-nonyl]adenine

  摘要：

  The synthesis of various chiral derivatives of (+)-erythro-9-(2-hydroxy-3-nonyl)adenine, (+)-EHNA, from (2S,3R)-3-amino-1,2-O-isopropylidene-1,2-nonanediol by condensation with 5-amino-4,6-dichloropyrimidine is described. The compounds synthesized were Cl'- and nor-Cl'-(+)-EHNA derivatives. When tested with calf spleen ADA, Cl'-OH- and nor-Cl'-(+)-EHNA had comparable inhibitory activity that was 1 order of magnitude lower than that of (+)-EHNA. Potency was reduced further in nor-Cl' derivatives.

  DOI：

  10.1021/jm00100a025

文献信息

• Adenosine deaminase inhibitors. Synthesis and biological evaluation of C1' and nor-C1' derivatives of (+)-erythro-9-[2(S)-hydroxy-3(R)-nonyl]adenine
  作者：Geraldine C. B. Harriman、Anne F. Poirot、Elie Abushanab、Rose Marie Midgett、Johanna D. Stoeckler

  DOI：10.1021/jm00100a025

  日期：1992.10

  The synthesis of various chiral derivatives of (+)-erythro-9-(2-hydroxy-3-nonyl)adenine, (+)-EHNA, from (2S,3R)-3-amino-1,2-O-isopropylidene-1,2-nonanediol by condensation with 5-amino-4,6-dichloropyrimidine is described. The compounds synthesized were Cl'- and nor-Cl'-(+)-EHNA derivatives. When tested with calf spleen ADA, Cl'-OH- and nor-Cl'-(+)-EHNA had comparable inhibitory activity that was 1 order of magnitude lower than that of (+)-EHNA. Potency was reduced further in nor-Cl' derivatives.