5-amino-6-chloro-4-<<1,2(S)-(isopropylidenedioxy)-3(R)-nonyl>amino>pyrimidine | 143707-11-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 5-amino-6-chloro-4-<<1,2(S)-(isopropylidenedioxy)-3(R)-nonyl>amino>pyrimidine
• 英文别名: 5-amino-6-chloro-4-{[1,2(S)-(isopropylidenedioxy)-3(R)-nonyl]amino}pyrimidine；6-chloro-4-N-[(1R)-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]heptyl]pyrimidine-4,5-diamine
• CAS: 143707-11-3
• 化学式: C₁₆H₂₇ClN₄O₂
• 分子量: 342.869
• InChiKey: MDRSPZQQAYTVHK-NEPJUHHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.61
• 重原子数：
  23.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  82.29
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  5-amino-6-chloro-4-<<1,2(S)-(isopropylidenedioxy)-3(R)-nonyl>amino>pyrimidine 在 吡啶 、 盐酸 、 氨 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 120.0h， 生成 9-(RS)-(1,2-Dihydroxy-3-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
• 作为产物：
  描述：

  magnesium,pentane,chloride 在 吡啶 、 lithium aluminium tetrahydride 、 sodium azide 、 dilithium tetrachlorocuprate 、 三正丁胺 作用下， 以 乙醚 、 二氯甲烷 、 戊醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.75h， 生成 5-amino-6-chloro-4-<<1,2(S)-(isopropylidenedioxy)-3(R)-nonyl>amino>pyrimidine
  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.