3'-(p-tolylthio)-2',3'-dideoxythymidine | 115913-89-8

• 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: 3'-(p-tolylthio)-2',3'-dideoxythymidine
• 英文别名: 3'-Tolylthio-3'-deoxythymidine；1-[(2R,4S,5R)-5-(hydroxymethyl)-4-(4-methylphenyl)sulfanyloxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 115913-89-8
• 化学式: C₁₇H₂₀N₂O₄S
• 分子量: 348.423
• InChiKey: ADXWQPFQSDKRMV-QLFBSQMISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  104
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-(2-deoxy-3-O-mesyl-β-D-threo-pentofuranosyl)thymine 、 4-甲苯硫酚 在 sodium ethanolate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以52%的产率得到3'-(p-tolylthio)-2',3'-dideoxythymidine
  参考文献：
  名称：

  Synthesis and anti-HIV activity of different sugar-modified pyrimidine and purine nucleosides

  摘要：

  A series of base-modified pyrimidine 3'-azido-2',3'-dideoxynucleosides and 3'-substituted purine and pyrimidine 2',3'-dideoxynucleosides have been synthesized and evaluated for their inhibitory activity against human immunodeficiency virus (HIV) replication in MT-4 cells. The following pyrimidine derivatives emerged as the most potent and/or selective inhibitors of HIV-induced cytopathogenicity (in order of decreasing selectivity: 3'-azido-3'-deoxythymidine (AZT), 3'-azido-2',3'-dideoxyuridine (AzddUrd), 3'-azido-2',3'-dideoxy-5-methylcytidine (AzddMeCyd), 3'-fluoro-ddUrd (FddUrd), 3'-fluoro-ddThd (FddThd), the N4-hydroxylated derivative of AzddMeCyd and the N4-methylated derivative of AzddMeCyd. Among the purine 2',3'-dideoxynucleosides, 3'-azido-2',3'-dideoxyguanosine (AzddGuo), 3'-fluoro-ddGuo (FddGuo), and 3'-fluoro-2,6-diaminopurine 2',3'-dideoxynucleoside (FddDAPR) were the most selective inhibitors of HIV replication.

  DOI：

  10.1021/jm00118a033

文献信息

• HERDEWIJN, PIET;BALZARINI, JAN;BADA, MASANORI;PAUWELS, RUDI;VAN, AERSCHOT+, J. MED. CHEM., 31,(1988) N 10, C. 2040-2048
  作者：HERDEWIJN, PIET、BALZARINI, JAN、BADA, MASANORI、PAUWELS, RUDI、VAN, AERSCHOT+

  DOI：——

  日期：——
• Synthesis and anti-HIV activity of different sugar-modified pyrimidine and purine nucleosides
  作者：Piet Herdewijn、Jan Balzarini、Masanori Baba、Rudi Pauwels、Arthur Van Aerschot、Gerard Janssen、Erik De Clercq

  DOI：10.1021/jm00118a033

  日期：1988.10

  A series of base-modified pyrimidine 3'-azido-2',3'-dideoxynucleosides and 3'-substituted purine and pyrimidine 2',3'-dideoxynucleosides have been synthesized and evaluated for their inhibitory activity against human immunodeficiency virus (HIV) replication in MT-4 cells. The following pyrimidine derivatives emerged as the most potent and/or selective inhibitors of HIV-induced cytopathogenicity (in order of decreasing selectivity: 3'-azido-3'-deoxythymidine (AZT), 3'-azido-2',3'-dideoxyuridine (AzddUrd), 3'-azido-2',3'-dideoxy-5-methylcytidine (AzddMeCyd), 3'-fluoro-ddUrd (FddUrd), 3'-fluoro-ddThd (FddThd), the N4-hydroxylated derivative of AzddMeCyd and the N4-methylated derivative of AzddMeCyd. Among the purine 2',3'-dideoxynucleosides, 3'-azido-2',3'-dideoxyguanosine (AzddGuo), 3'-fluoro-ddGuo (FddGuo), and 3'-fluoro-2,6-diaminopurine 2',3'-dideoxynucleoside (FddDAPR) were the most selective inhibitors of HIV replication.