2',3'-di-O-acetyl-6-N-(4-nitrobenzyl)-5'-S-[2-(trifluoroacetamido)ethyl]-5'-thioadenosine | 1240043-78-0

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 2',3'-di-O-acetyl-6-N-(4-nitrobenzyl)-5'-S-[2-(trifluoroacetamido)ethyl]-5'-thioadenosine
• 英文别名: [(2S,3S,4R,5R)-4-acetyloxy-5-[6-[(4-nitrophenyl)methylamino]purin-9-yl]-2-[2-[(2,2,2-trifluoroacetyl)amino]ethylsulfanylmethyl]oxolan-3-yl] acetate
• CAS: 1240043-78-0
• 化学式: C₂₅H₂₆F₃N₇O₈S
• 分子量: 641.585
• InChiKey: KVYHMDIDFFNLON-ZDXOVATRSA-N

物化性质

• 密度：
  1.61±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  44
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  218
• 氢给体数：
  2
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  2',3'-di-O-acetyl-6-N-(4-nitrobenzyl)-5'-S-[2-(trifluoroacetamido)ethyl]-5'-thioadenosine 在 ammonium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 6.0h， 生成 (2S,3S,4R,5R)-2-(2-氨基乙基硫基甲基)-5-[6-[(4-硝基苯基)甲基氨基]嘌呤-9-基]四氢呋喃-3,4-二醇
  参考文献：
  名称：

  Improved Syntheses of 5′-S-(2-Aminoethyl)-6-N-(4-nitrobenzyl)-5′-thioadenosine (SAENTA), Analogues, and Fluorescent Probe Conjugates: Analysis of Cell-Surface Human Equilibrative Nucleoside Transporter 1 (hENT1) Levels for Prediction of the Antitumor Efficacy of Gemcitabine

  摘要：

  5'-S-(2-Aminoethyl)-6-N-(4-nitrobenzyl)-5'-thioadenosine (SAENTA), 5'-S-(2-acetamidoethyl)-6-N-[(4-substituted)benzyl]-5'-thioadenosine analogues, 5'-S-[2-(6-aminohexanamido)lethyl-6-N-(4-nitrobenzyl)-5'-thioadenosine (SAHENTA), and related compounds were synthesized by S(N)Ar displacement of fluoride from 6-fluoropurine intermediates with 4-(substituted)benzylamines. Conjugation of the pendant amino groups of SAENTA and SAHENTA with fluorescein-5-yl isothiocyanate (FITC) gave fluorescent probes that bound at nanomolar concentrations specifically to human equilibrative nucleoside transporter 1 (hENT1) produced in recombinant form in model expression systems and in native form in cancer cell lines. Transporter binding effects were studied and the ability of the probes to predict the potential antitumor efficacy of 2'-deoxy-2',2'-difluorocylidine (gemcitabine) was demonstrated.

  DOI：

  10.1021/jm100432w
• 作为产物：
  描述：

  9-{2,3-di-O-acetyl-5-S-[2-(trifluoroacetamido)ethyl]-5-thio-β-D-ribofuranosyl}-6-fluoropurine 、 4-硝基苄胺盐酸盐 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以88%的产率得到2',3'-di-O-acetyl-6-N-(4-nitrobenzyl)-5'-S-[2-(trifluoroacetamido)ethyl]-5'-thioadenosine
  参考文献：
  名称：

  Improved Syntheses of 5′-S-(2-Aminoethyl)-6-N-(4-nitrobenzyl)-5′-thioadenosine (SAENTA), Analogues, and Fluorescent Probe Conjugates: Analysis of Cell-Surface Human Equilibrative Nucleoside Transporter 1 (hENT1) Levels for Prediction of the Antitumor Efficacy of Gemcitabine

  摘要：

  5'-S-(2-Aminoethyl)-6-N-(4-nitrobenzyl)-5'-thioadenosine (SAENTA), 5'-S-(2-acetamidoethyl)-6-N-[(4-substituted)benzyl]-5'-thioadenosine analogues, 5'-S-[2-(6-aminohexanamido)lethyl-6-N-(4-nitrobenzyl)-5'-thioadenosine (SAHENTA), and related compounds were synthesized by S(N)Ar displacement of fluoride from 6-fluoropurine intermediates with 4-(substituted)benzylamines. Conjugation of the pendant amino groups of SAENTA and SAHENTA with fluorescein-5-yl isothiocyanate (FITC) gave fluorescent probes that bound at nanomolar concentrations specifically to human equilibrative nucleoside transporter 1 (hENT1) produced in recombinant form in model expression systems and in native form in cancer cell lines. Transporter binding effects were studied and the ability of the probes to predict the potential antitumor efficacy of 2'-deoxy-2',2'-difluorocylidine (gemcitabine) was demonstrated.

  DOI：

  10.1021/jm100432w