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-methylthymine | 1054722-81-4

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 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-methylthymine
• 英文别名: N-[(2S,3R,4R,5R)-4-[tert-butyl(dimethyl)silyl]oxy-3-cyano-5-(3,5-dimethyl-2,4-dioxopyrimidin-1-yl)-2-(phenylmethoxymethyl)oxolan-3-yl]-N-methylmethanesulfonamide
• CAS: 1054722-81-4
• 化学式: C₂₇H₄₀N₄O₇SSi
• 分子量: 592.789
• InChiKey: SEHRLEIKFIDYDF-JVOXNHGTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.51
• 重原子数：
  40
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  138
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  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-methylthymine 在 caesium carbonate 作用下， 以 乙腈 为溶剂， 反应 15.0h， 以30%的产率得到[1-[5'-O-benzyl-2'-O-tert-butyldimethylsilyl-β-D-ribofuranosyl]-3-N-methylthymine]-3'-spiro-3''-(4''-amino-2'',3''-dihydro-2''-N-methyl-1'',1''-dioxo-isothiazole)
  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
• 作为产物：
  描述：

  1-(3'-amino-5'-O-benzyl-2'-O-tert-butyldimethylsilyl-3'-C-cyano-3'-deoxy-3'-N-mesyl-β-D-ribofuranosyl)thymine 、 碘甲烷 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 9.0h， 以87%的产率得到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-methylthymine
  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

• 10.1081/ncn-120022690
  作者：Van Nhien, Albert Nguyen、Tomassi, Cyrille、Len, Christophe、Marco-Contelles, Jose Luis、Postel, Denis

  DOI：10.1081/ncn-120022690

  日期：——
• 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.