TsTh | 68696-86-6

• 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: TsTh
• 英文别名: 1,3-Dimethyl-7-(4-methylphenyl)sulfonylpurine-2,6-dione；1,3-dimethyl-7-(4-methylphenyl)sulfonylpurine-2,6-dione
• CAS: 68696-86-6
• 化学式: C₁₄H₁₄N₄O₄S
• 分子量: 334.356
• InChiKey: LVWRZFYEJXBCQY-UHFFFAOYSA-N

物化性质

• 沸点：
  568.8±60.0 °C(Predicted)
• 密度：
  1.50±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  101
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  TsTh 、 苯乙醇 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以92%的产率得到1,3-dimethyl-7-phenethyl-1H-purine-2,6(3H,7H)-dione
  参考文献：
  名称：

  N 7-Tosyltheophylline (TsTh): A Highly Efficient Reagent for the One-Pot Synthesis of N 7-Alkyltheophyllines from Alcohols

  摘要：

  A convenient and highly efficient one-pot N-alkylation of theophylline from alcohols via N-7-tosyltheophylline (TsTh) is described. In this protocol, the treatment of primary and/or secondary alcohols with a mixture of TsTh and 1,8-diazabicyclo[5.4.0]undec-7-ene in refluxing acetonitrile affords the corresponding N-7-alkyltheophylline in good to excellent yields; the reaction was optimized for solvent and base. This methodology is highly efficient for various structurally diverse primary and secondary alcohols. A plausible mechanism for the one-pot N-alkylation of theophylline with alcohols via TsTh has been suggested.

  DOI：

  10.1055/s-0033-1341026
• 作为产物：
  描述：

  茶碱 、 对甲苯磺酰氯 在 三乙胺 作用下， 以 乙腈 为溶剂， 以96%的产率得到TsTh
  参考文献：
  名称：

  N 7-Tosyltheophylline (TsTh): A Highly Efficient Reagent for the One-Pot Synthesis of N 7-Alkyltheophyllines from Alcohols

  摘要：

  A convenient and highly efficient one-pot N-alkylation of theophylline from alcohols via N-7-tosyltheophylline (TsTh) is described. In this protocol, the treatment of primary and/or secondary alcohols with a mixture of TsTh and 1,8-diazabicyclo[5.4.0]undec-7-ene in refluxing acetonitrile affords the corresponding N-7-alkyltheophylline in good to excellent yields; the reaction was optimized for solvent and base. This methodology is highly efficient for various structurally diverse primary and secondary alcohols. A plausible mechanism for the one-pot N-alkylation of theophylline with alcohols via TsTh has been suggested.

  DOI：

  10.1055/s-0033-1341026

文献信息

• Synthesis and Evaluation as a Blood–Brain Barrier-Permeable Probe of 7-<i>N</i>-(PROXYL-3-yl-methyl)theophylline
  作者：Miho C. Emoto、Kota Sasaki、Koya Maeda、Hirotada G. Fujii、Shingo Sato

  DOI：10.1248/cpb.c18-00333

  日期：2018.9.1

  The drug-nitroxide radical hybrid-compound 7-N-((2,2,5,5-tetramethylpyrrolidine-1-yloxy(PROXYL))-3-yl-methyl)theophylline (3) was synthesized by coupling 7-N-tosyltheophylline with 3-hydroxymethyl-PROXYL, HMP). The stability of 3 relative to that of HMP was examined in the presence of the anti-oxidant, ascorbic acid (AsA). The initial reduction rate constants of 3 and HMP were 11.9±5.3 and 6.1±5.2 M−1 min−1, respectively. In the presence of glutathione (GSH), these constants increased slightly to 22.3±6.8 and 9.1±2.4 M−1 min−1, respectively. Two-dimensional cranial electron paramagnetic resonance imaging of mice intravenously injected with 3 via the tail vein revealed that probe 3 enters the mouse brain by passing through the blood–brain barrier (BBB).

  药物-氮氧自由基杂化化合物7-N-((2,2,5,5-四甲基吡咯烷-1-基氧基(PROXYL))-3-基甲基)茶碱(3)是通过7-N-甲苯磺酰基茶碱与3-羟甲基-PROXYL(HMP)的耦合反应合成的。在抗氧化剂抗坏血酸(AsA)的存在下，研究了3相对于HMP的稳定性。3和HMP的初始还原速率常数分别为11.9±5.3和6.1±5.2 M−1 min−1。在谷胱甘肽(GSH)的存在下，这些常数略有增加，分别为22.3±6.8和9.1±2.4 M−1 min−1。通过尾静脉静脉注射3的小鼠二维颅脑电子顺磁共振成像显示，探针3通过血脑屏障(BBB)进入小鼠大脑。