3'-N-cyano-O-isophenylurea-3'-deoxythymidine | 142543-82-6

• 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'-N-cyano-O-isophenylurea-3'-deoxythymidine
• 英文别名: 3-cyano-1-[(2S,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)tetrahydrofuran-3-yl]-2-phenyl-isourea；phenyl N-cyano-N'-[(2S,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]carbamimidate
• CAS: 142543-82-6
• 化学式: C₁₈H₁₉N₅O₅
• 分子量: 385.379
• InChiKey: NFZXWPYLQJBZDB-RRFJBIMHSA-N

物化性质

• 密度：
  1.46±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  136
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3'-N-cyano-O-isophenylurea-3'-deoxythymidine 在 氨 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 18.0h， 以45%的产率得到3'-N-cyanoguanidino-3'-deoxythymidine
  参考文献：
  名称：

  Synthesis and evaluation of new 2′,3′-dideoxynucleoside analogs as potential anti-AIDS and anti-herpes drugs

  摘要：

  Based on the known structure-activity relationships for the active anti-HIV, a series of 3'-deoxy-3'-N-functionalized thymidine analogs has been synthesized from thymidine. Evaluation for inhibitory activity against human immunodeficiency virus (HIV) replication in CEM cells and against herpes simplex virus in MRC-5 cells is reported.

  DOI：

  10.1016/0223-5234(92)90102-7
• 作为产物：
  描述：

  齐多夫定 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 异丙醇 为溶剂， 反应 41.0h， 生成 3'-N-cyano-O-isophenylurea-3'-deoxythymidine
  参考文献：
  名称：

  Synthesis and evaluation of new 2′,3′-dideoxynucleoside analogs as potential anti-AIDS and anti-herpes drugs

  摘要：

  Based on the known structure-activity relationships for the active anti-HIV, a series of 3'-deoxy-3'-N-functionalized thymidine analogs has been synthesized from thymidine. Evaluation for inhibitory activity against human immunodeficiency virus (HIV) replication in CEM cells and against herpes simplex virus in MRC-5 cells is reported.

  DOI：

  10.1016/0223-5234(92)90102-7

文献信息

• Synthesis and antiviral evaluation of 3′-substituted thymidine analogues derived from 3′-amino-3′-deoxythymidine
  作者：Christophe Pannecouque、Roger Busson、Jan Balzarini、Paul Claes、Erik De Clercq、Piet Herdewijn

  DOI：10.1016/0040-4020(95)00198-h

  日期：1995.5

  series of 3′-deoxy-3′-N-functionalized thymidine analogues derived from 3′-amino-3′-deoxythymidine was synthesized. These compounds were evaluated for their antiviral activity. Three of the prepared molecules namely 3′-(1,2,4-triazol-1-yl)carbimidoylamino-3′-deoxythymidine 6, 3′-(3-amino-1-methyl-1,2,4-triazol-5-yl)amino-3′-deoxythymidine 8b and 3′-N-cyano-O-phenylisourea-3′-deoxythymidine 7 show moderate

  基于抗病毒活性的结构-活性关系，一系列的3'-脱氧-3' - ñ -官能化从3'-氨基-3'-脱氧胸苷合成衍生的胸苷类似物。评价这些化合物的抗病毒活性。三个所制备的分子即3' - （1,2,4-三唑-1-基）carbimidoylamino -3'-脱氧胸苷6，3' - （3-氨基-1-甲基-1,2,4-三唑5-基）氨基-3′-脱氧胸苷8b和3′- N-氰基-O-苯基异脲-3′-脱氧胸苷7对HIV-1和HIV-2表现出中等但选择性的体外活性。这些数据表明3'-位的一些空间体积与抗HIV活性是相容的