3'-[(氨基羰基)氨基]-3'-脱氧胸苷 | 135593-79-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 中文名称: 3'-[(氨基羰基)氨基]-3'-脱氧胸苷
• 英文名称: 3'-ureido-3'-deoxythymidine
• 英文别名: [(2S,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]urea
• CAS: 135593-79-2
• 化学式: C₁₁H₁₆N₄O₅
• 分子量: 284.272
• InChiKey: VPQVLWCZGHVVOR-XLPZGREQSA-N

物化性质

• 熔点：
  178 °C
• 密度：
  1.50±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  134
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  齐多夫定 在 ammonium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 0.75h， 生成 3'-[(氨基羰基)氨基]-3'-脱氧胸苷
  参考文献：
  名称：

  Habich, Synthesis, 1992, # 4, p. 358 - 360

  摘要：

  DOI：

文献信息

• Synthesis and Antiviral Evaluation of 3'-Substituted Thymidine Analogues Derived from 3'-Amino-3'-deoxythymidine
  作者：C. Pannecouque、K. Van Poppel、J. Balzarini、P. Claes、E. De Clercq、P. Herdewijn

  DOI：10.1080/15257779508012422

  日期：1995.5.1

  Abstract To assess the structure-activity relationship for antiviral activity, a series of 3′-deoxy-3′-N-functionalized thymidine analogues were synthesized. Several of these thymidine analogues show moderate in vitro activity against HIV-1 and HIV-2.

  摘要为评估抗病毒活性的构效关系，合成了一系列3'-脱氧-3'-N-官能化胸苷类似物。这些胸苷类似物中的几种显示出对HIV-1和HIV-2的适度体外活性。
• 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
• Design and synthesis of the 3′-aminocarbonylamino, aminothiocarbonylamino and<i>N</i>-(Hydroxy)guanidinyl derivatives of thymidine as potential anti-HIV agents
  作者：Kevin W. Morin、Rakesh Kumar、Edward E. Knaus、Leonard I. Wiebe

  DOI：10.1002/jhet.5570280346

  日期：1991.4

  The 3′-substituted-3′-deoxythymidines 3a (urea), 3b (thiourea) and 3c [N-(hydroxy)guanidinyl)] were designed based on the known structure-activity correlations for the active anti-HIV agent, 3′-azido-3′-deoxythymidine (AZT). Hydrolysis of 3′-cyanamido-3′-deoxythymidine (2) with ammonium hydroxide in the presence of hydrogen peroxide afforded the 3′-urea analogue 3a, whereas reaction with hydrogen sulfide

  基于活性抗HIV剂3'的已知结构-活性相关性，设计了3'-取代的3'-脱氧胸苷3a（尿素），3b（硫脲）和3c [ N-（羟基）胍基）。 -叠氮基3'-脱氧胸苷（AZT）。在过氧化氢存在下用氢氧化铵水解3'-氰基氨基-3'-脱氧胸苷（2），得到3'-脲类似物3a，而在甲醇中与硫化氢反应得到3'-硫脲衍生物3b。3′-[ N-（羟基）胍基]化合物3c是通过3′-氰胺2与羟胺反应合成的。
• Synthesis and evaluation of new 2′,3′-dideoxynucleoside analogs as potential anti-AIDS and anti-herpes drugs
  作者：A Faraj、M Maillard、M Lemaître、S Letellier、F Frappier、JC Florent、DS Grierson、C Monneret、A Zerial

  DOI：10.1016/0223-5234(92)90102-7

  日期：1992.3

  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.
• MORIN, KEVIN W.;KUMAR, RAKESH;KNAUS, EDWARD E.;WIEBE, LEONARD I., J. HETEROCYCL. CHEM., 28,(1991) N, C. 807-809
  作者：MORIN, KEVIN W.、KUMAR, RAKESH、KNAUS, EDWARD E.、WIEBE, LEONARD I.

  DOI：——

  日期：——