2-Acetylamino-N-[(3aR,4R,6R,6aR)-6-(6-amino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl]-3-mercapto-3-methyl-butyramide | 372517-87-8

• 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: 2-Acetylamino-N-[(3aR,4R,6R,6aR)-6-(6-amino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl]-3-mercapto-3-methyl-butyramide
• CAS: 372517-87-8
• 化学式: C₂₀H₂₉N₇O₅S
• 分子量: 479.56
• InChiKey: NEZVVJUQMUTYIM-YKSAAAQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.16
• 重原子数：
  33.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  155.51
• 氢给体数：
  4.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  2-Acetylamino-N-[(3aR,4R,6R,6aR)-6-(6-amino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl]-3-mercapto-3-methyl-butyramide 在 甲酸 作用下， 以 水 为溶剂， 反应 48.0h， 以100%的产率得到2-acetamido-N-[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl]-3-methyl-3-sulfanylbutanamide
  参考文献：
  名称：

  Synthesis, electrochemical, and spectroscopic studies of novel S-nitrosothiols

  摘要：

  A series of S-nitrosothiol compounds, structurally related to the NO-donor S-nitroso-N-acetyl-D,L-penicillamine (SNAP) that contain amidin groups were synthesised by S-nitrosation of the corresponding thiols and characterised. The kinetics of decomposition were investigated and showed that the two adenine-based thionitrites exhibited an unusual stability in aqueous solution compared to SNAP, suggesting that these compounds may complex the traces of free copper ions present in solution, which is known to catalyze the decomposition of thionitrites. The electrochemical behaviour of these compounds and their nitric oxide-releasing potential were studied by means of cyclic voltammetry techniques on mercury and glassy carbon electrodes. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00694-9
• 作为产物：
  描述：

  DL-青霉胺 在 吡啶 作用下， 生成 2-Acetylamino-N-[(3aR,4R,6R,6aR)-6-(6-amino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl]-3-mercapto-3-methyl-butyramide
  参考文献：
  名称：

  Synthesis and uptake of nitric oxide-releasing drugs by the p2 nucleoside transporter in Trypanosoma equiperdum

  摘要：

  A series of S-nitrosothiols, structurally related to the NO.-donor S-nitroso-N-acetylpenicillamine, and of organic nitrate esters that contain amidine groups which specify a recognition via the trypanosomal purine transporter P2, were synthesized and tested for their ability to inhibit the uptake of [2-H-3]adenosine on Trypanosoma equiperdum. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00233-x