1-(2-Deoxy-β-D-erythro-pentofuranosyl)-4-(1,2,4-triazol-1-yl)-2(1H)-pyrimidinone | 109389-24-4

• 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: 1-(2-Deoxy-β-D-erythro-pentofuranosyl)-4-(1,2,4-triazol-1-yl)-2(1H)-pyrimidinone
• 英文别名: 1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-4-(1,2,4-triazol-1-yl)pyrimidin-2-one；1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-(1,2,4-triazol-1-yl)pyrimidin-2-one
• CAS: 109389-24-4
• 化学式: C₁₁H₁₃N₅O₄
• 分子量: 279.255
• InChiKey: YMWLMFYATBPASE-QXFUBDJGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  113
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(2-Deoxy-β-D-erythro-pentofuranosyl)-4-(1,2,4-triazol-1-yl)-2(1H)-pyrimidinone 以 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 生成 N⁴-ureidocarbonyl-5'-O-di(p-anisyl)phenylmethyl-2'-deoxycytidine-3'-(β-cyanoethyl N,N-diisopropylphosphoramidite)
  参考文献：
  名称：

  The Design and Synthesis ofN⁴-Anthraniloyl-2′-dC, the Improved Syntheses ofN⁴-Carbamoyl-andN⁴-Ureidocarbamoyl-2′-dC, Incorporation into Oligonucleotides and Triplex Formation Testing

  摘要：

  Three modified nucleosides were designed with the aim of achieving triplet formation with the CG base pair of duplex DNA. Direct anthraniloylation of 2'-deoxycytidine, using isatoic anhydride afforded the novel N-4-anthraniloyl-2'-deoxycyridine. Much improved preparations of N-4-carbamoyl-2'-deoxycytidine and of N-4-ureidocarbonyl-2'-deoxycytidine were accomplished. The modified nucleosides were incorporated into oligonucleotides. Thermal denaturation studies and gel mobility shift analysis suggest that these nucleosides do not form base triplets with any of the four base pairs of DNA.

  DOI：

  10.1080/07328319808004232
• 作为产物：
  描述：

  在 吡啶 、 silica gel 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 72.0h， 生成 1-(2-Deoxy-β-D-erythro-pentofuranosyl)-4-(1,2,4-triazol-1-yl)-2(1H)-pyrimidinone
  参考文献：
  名称：

  Synthesis and anti-HIV activity of C4-modified pyrimidine nucleosides

  摘要：

  One-pot syntheses provided a series of triazole- and pentafluorophenyloxy-substituted pyrimidine nucleosides. Most of the compounds in the series displayed anti-HIV activities but none as potent as AZT 2. 1-(beta-D-Erythro-pentofuranosyl)-4-pentafluorophenyloxy-2(1H)-pyr imidinone 14 was the most potent and the most selective compound in the series with EC50 = 1.6 microM.

  DOI：

  10.1016/s0014-827x(98)00107-4

文献信息

• Direct synthesis, substitution, and structure of 1-(2′-deoxyβ-D-erythro-pentofuranosyl)-4-pentafluorophenylpyrimidin-2H-one
  作者：Mark P. Wallis、Ian D. Spiers、Carl H. Schwalbe、William Fraser

  DOI：10.1016/0040-4039(95)00587-3

  日期：1995.5

  Direct methods have been developed to access the title nucleoside 1 from 2′-deoxyuridine (dU). The C-4 pentafluorophenyl group of 1 is readily displaced by amine nucleophiles forming N-4 substituted cytosines in good to excellent yields.

  已经开发了直接方法以从2'-脱氧尿苷（dU）访问标题核苷1。的C-4五氟苯基1可容易地通过形成良好N-4取代的胞嘧啶到优异的产率胺亲核试剂置换。
• The Design and Synthesis of<i>N</i>⁴-Anthraniloyl-2′-dC, the Improved Syntheses of<i>N</i>⁴-Carbamoyl-and<i>N⁴-</i>Ureidocarbamoyl-2′-dC, Incorporation into Oligonucleotides and Triplex Formation Testing
  作者：Nancy Guzzo-Pernell、Geoff W Tregear、Jim Haralambidis、John M Lawlor

  DOI：10.1080/07328319808004232

  日期：1998.7

  Three modified nucleosides were designed with the aim of achieving triplet formation with the CG base pair of duplex DNA. Direct anthraniloylation of 2'-deoxycytidine, using isatoic anhydride afforded the novel N-4-anthraniloyl-2'-deoxycyridine. Much improved preparations of N-4-carbamoyl-2'-deoxycytidine and of N-4-ureidocarbonyl-2'-deoxycytidine were accomplished. The modified nucleosides were incorporated into oligonucleotides. Thermal denaturation studies and gel mobility shift analysis suggest that these nucleosides do not form base triplets with any of the four base pairs of DNA.
• Synthesis and anti-HIV activity of C4-modified pyrimidine nucleosides
  作者：Mark P Wallis、Naheed Mahmood、William Fraser

  DOI：10.1016/s0014-827x(98)00107-4

  日期：1999.1

  One-pot syntheses provided a series of triazole- and pentafluorophenyloxy-substituted pyrimidine nucleosides. Most of the compounds in the series displayed anti-HIV activities but none as potent as AZT 2. 1-(beta-D-Erythro-pentofuranosyl)-4-pentafluorophenyloxy-2(1H)-pyr imidinone 14 was the most potent and the most selective compound in the series with EC50 = 1.6 microM.