(2S,3R)-3-amino-1,2-O-isopropylidene-1,2-nonanediol | 143707-10-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R)-3-amino-1,2-O-isopropylidene-1,2-nonanediol
• 英文别名: (1R)-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]heptan-1-amine
• CAS: 143707-10-2
• 化学式: C₁₂H₂₅NO₂
• 分子量: 215.336
• InChiKey: YPFSDKSMXYJFSM-MNOVXSKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  44.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,3R)-3-amino-1,2-O-isopropylidene-1,2-nonanediol 在 吡啶 、 盐酸 、 三正丁胺 、 氨 作用下， 以 乙醇 、 二氯甲烷 、 戊醇 为溶剂， 反应 150.0h， 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 作用下， 以 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.75h， 生成 (2S,3R)-3-amino-1,2-O-isopropylidene-1,2-nonanediol
  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 4-amino-1-[2(S)-hydroxy-3(R)-nonyl]-1H-imidazo[4,5-c]pyridine [3-deaza-(+)-EHNA] and certain C1' derivatives
  作者：Geraldine C. B. Harriman、Elie Abushanab、Johanna D. Stoeckler

  DOI：10.1021/jm00028a014

  日期：1994.1

  The synthesis of the title compound (15) and its 1'-fluoro (14) and 1'-hydroxy (12) derivatives is described. Key intermediate 10 was obtained by two routes through condensation of (2R,3R)-3-amino-1,2-O-isopropylidene-1,2-nonanediol (3) with either 2,4-dichloro- or 4-chloro-3-nitropyridine. When assayed as adenosine deaminase inhibitors, 15 was found to be almost twice as active as its racemate. While hydroxylation at the 1'-position resulted in an 80-fold decrease in activity, the 1'-fluoro derivative proved to have activity comparable to that of 3-deaza-(+)-EHNA.
• 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.