3-amino-5-O-benzyl-3-C-cyano-3-deoxy-3-N-mesyl-1,2-O-sulfinyl-α-D-ribofuranose

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-amino-5-O-benzyl-3-C-cyano-3-deoxy-3-N-mesyl-1,2-O-sulfinyl-α-D-ribofuranose
• 英文别名: N-[(3aR,5S,6R,6aR)-6-cyano-2-oxo-5-(phenylmethoxymethyl)-5,6a-dihydro-3aH-furo[2,3-d][1,3,2]dioxathiol-6-yl]methanesulfonamide
• 化学式: C₁₄H₁₆N₂O₇S₂
• 分子量: 388.422
• InChiKey: NZHLCWYNJVBOPH-IDKAXHJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  152
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  3-amino-5-O-benzyl-3-C-cyano-3-deoxy-3-N-mesyl-1,2-O-sulfinyl-α-D-ribofuranose 在 吡啶 、 咪唑 、 ammonium sulfate 、 potassium carbonate 、 六甲基二硅氮烷 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 15.75h， 生成 1-(3'-amino-5'-O-benzyl-2'-O-tert-butyldimethylsilyl-3'-C-cyano-3'-deoxy-3'-N-mesyl-3'-N-methyl-β-D-ribofuranosyl)-3-N-tert-butoxycarbonylthymine
  参考文献：
  名称：

  First Synthesis and Evaluation of the Inhibitory Effects of Aza Analogues of TSAO on HIV-1 Replication

  摘要：

  Aza TSAO-T derivatives bearing a dihydroisothiazole dioxide ring instead of an oxathiole dioxide ring at the C-3 ' position on the sugar moiety were prepared. We have synthesized four families of compounds depending on substitution at both N-3 and N-2 ''. Biological evaluation showed that these compounds are HIV-1(IIIB)-specific and potent reverse transcriptase inhibitors with EC50 values between 0.13 and 3.5 mu M in cell culture.

  DOI：

  10.1021/jm050091g

文献信息

• First Synthesis and Evaluation of the Inhibitory Effects of Aza Analogues of TSAO on HIV-1 Replication
  作者：Albert Nguyen Van Nhien、Cyrille Tomassi、Christophe Len、José Luis Marco-Contelles、Jan Balzarini、Christophe Pannecouque、Erik De Clercq、Denis Postel

  DOI：10.1021/jm050091g

  日期：2005.6.1

  Aza TSAO-T derivatives bearing a dihydroisothiazole dioxide ring instead of an oxathiole dioxide ring at the C-3 ' position on the sugar moiety were prepared. We have synthesized four families of compounds depending on substitution at both N-3 and N-2 ''. Biological evaluation showed that these compounds are HIV-1(IIIB)-specific and potent reverse transcriptase inhibitors with EC50 values between 0.13 and 3.5 mu M in cell culture.