2-chloro-4-<(1,2(R)-dihydroxy-1,2-O-isopropylidene-3(R)-nonyl)amino>-3-nitropyridine | 153185-92-3

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 2-chloro-4-<(1,2(R)-dihydroxy-1,2-O-isopropylidene-3(R)-nonyl)amino>-3-nitropyridine
• 英文别名: 2-chloro-N-[(1R)-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]heptyl]-3-nitropyridin-4-amine
• CAS: 153185-92-3
• 化学式: C₁₇H₂₆ClN₃O₄
• 分子量: 371.864
• InChiKey: MNQOWDFRDNNZQV-OCCSQVGLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  89.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-chloro-4-<(1,2(R)-dihydroxy-1,2-O-isopropylidene-3(R)-nonyl)amino>-3-nitropyridine 在 platinum(IV) oxide 盐酸 、 偶氮二甲酸二异丙酯 、 Amberlite IR-120 H+ resign 、 氢气 、 镍 、 三苯基膦 、 肼 作用下， 以 乙醇 、 水 、 苯 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 51.0h， 生成 4-amino-1-(1,2(R)-epoxy-3(R)-nonyl)-1H-imidazo<4,5-c>pyridine
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1021/jm00028a014
• 作为产物：
  描述：

  2,4-二氯-3-硝基吡啶 、 (2S,3R)-3-amino-1,2-O-isopropylidene-1,2-nonanediol 在 三乙胺 作用下， 以 硝基甲烷 为溶剂， 反应 1.0h， 以44%的产率得到2-chloro-4-<(1,2(R)-dihydroxy-1,2-O-isopropylidene-3(R)-nonyl)amino>-3-nitropyridine
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1021/jm00028a014

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.