8-[(6’-methylcoumarin-3’-yl)methylthio]guanosine | 1328880-85-8

• 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: 8-[(6’-methylcoumarin-3’-yl)methylthio]guanosine
• 英文别名: 8-[(6'-methylcoumarin-3'-yl)methylthio]guanosine
• CAS: 1328880-85-8
• 化学式: C₂₁H₂₁N₅O₇S
• 分子量: 487.493
• InChiKey: ZFLAUAXUYFZPLS-SCFUHWHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.02
• 重原子数：
  34.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  189.72
• 氢给体数：
  5.0
• 氢受体数：
  12.0

反应信息

• 作为产物：
  描述：

  8-溴鸟苷 在 ammonium hydroxide 、 硫脲 作用下， 以 乙醇 、 水 、 乙腈 为溶剂， 反应 0.5h， 生成 8-[(6’-methylcoumarin-3’-yl)methylthio]guanosine
  参考文献：
  名称：

  Development of New Sulfur-Containing Conjugated Compounds as Anti-HCV Agents

  摘要：

  Various conjugated compounds containing a coumarin moiety and a heterocyclic nucleus were synthesized. Their activity against hepatitis C virus was tested on subgenomic replicon replication in Huh 5-2 cells. Some heterobicycle-coumarin conjugates with the -S-CH2-linker were found to possess appealing antiviral activities. The sulfur atom in these conjugated compounds was found to be an essential element to their antiviral activity.

  DOI：

  10.1080/10426507.2010.520284

文献信息

• Synthesis and Structure-Activity Relationships of Imidazole-Coumarin Conjugates against Hepatitis C Virus
  作者：Shwu-Chen Tsay、Shu-Yu Lin、Wen-Chieh Huang、Ming-Hua Hsu、Kuo Hwang、Chun-Cheng Lin、Jia-Cherng Horng、I-Chia Chen、Jih Hwu、Fa-Kuen Shieh、Pieter Leyssen、Johan Neyts

  DOI：10.3390/molecules21020228

  日期：——

  experimental results indicate that of the twenty newly synthesized imidazole-coumarin conjugates, three of them exhibited appealing EC50 values (5.1-8.4 μM) and selective indices >20 against hepatitis C virus. Their potency and selectivity were increased substantially by modification of their structure with two factors: imidazole nucleus with a hydrogen atom at the N(1) position and coumarin nucleus

  以咪唑和香豆素衍生物为原料，通过化学方法合成了一系列带有-SCH2-键的新型共轭化合物。实验结果表明，在二十种新合成的咪唑-香豆素缀合物中，其中三种表现出吸引人的 EC50 值 (5.1-8.4 μM) 和针对丙型肝炎病毒的选择性指数 >20。通过用两个因素修改其结构，它们的效力和选择性得到显着提高：在 N(1) 位置带有氢原子的咪唑核和带有取代基（例如 Cl、F、Br、Me 和 OMe）的香豆素核。这些指南为进一步开发作为抗病毒剂的共轭化合物提供了有价值的信息。