3'-cyano-3'-deoxy-β-D-arabinofuranosylthymine | 115913-83-2

• 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'-cyano-3'-deoxy-β-D-arabinofuranosylthymine
• 英文别名: 1-(3-cyano-3-deoxy-β-D-arabinofuranosyl)thymine；(2S,3S,4S,5R)-4-hydroxy-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolane-3-carbonitrile
• CAS: 115913-83-2
• 化学式: C₁₁H₁₃N₃O₅
• 分子量: 267.241
• InChiKey: DWXOIPDJUIXUPY-BDNRQGISSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  123
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3'-cyano-3'-deoxy-β-D-arabinofuranosylthymine 生成 1-(3-脱氧-3-乙炔基-β-D-呋喃阿拉伯糖基)-5-甲基嘧啶-2,4(1H,3H)-二酮
  参考文献：
  名称：

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

  摘要：

  DOI：
• 作为产物：
  描述：

  1-(3-cyano-3-deoxy-5-O-trityl-β-D-arabinofuranosyl)thymine 在 甲酸 作用下， 反应 0.08h， 以74%的产率得到3'-cyano-3'-deoxy-β-D-arabinofuranosylthymine
  参考文献：
  名称：

  Synthesis and Anti-HIV Activity of 3'-Cyano-2',3'-dideoxythymidine and 3'-Cyano-2',3'-didehydro-2',3'-dideoxythymidine

  摘要：

  DOI：

  10.3987/com-88-4708

文献信息

• Synthesis of 3′-Cyano-3′-deoxy-β-D-<i>arabino</i>-nucleosides
  作者：Dieter Häbich、Wolfgang Barth

  DOI：10.1055/s-1988-27760

  日期：——

  The synthesis of 3′-cyano-3′-deoxy-β-D-arabino-nucleosides by regioselective ring cleavage of lyxo-epoxides with cyanodiethylalane is described.

  报道了通过氰基二乙基铝与木酮型环氧的区域选择性环裂解合成3′-氰基-3′-脱氧-β-D-阿拉伯糖核苷的方法。
• Synthesis and Anti-HIV Activity of 3'-Cyano-2',3'-dideoxythymidine and 3'-Cyano-2',3'-didehydro-2',3'-dideoxythymidine
  作者：Akira Matsuda、Mutsumi Satoh、Hideki Nakashima、Naoki Yamamoto、Tohru Ueda

  DOI：10.3987/com-88-4708

  日期：——
• 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.