1-(2-Deoxy-I(2)-D-erythro-pentofuranosyl)-1H-imidazo[4a(2),5a(2):4,5]thieno[3,2-d]pyrimidin-5-amine | 1160725-85-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并嘧啶酮衍生物
• 英文名称: 1-(2-Deoxy-I(2)-D-erythro-pentofuranosyl)-1H-imidazo[4a(2),5a(2):4,5]thieno[3,2-d]pyrimidin-5-amine
• 英文别名: (2R,3S,5R)-5-(9-amino-7-thia-3,5,10,12-tetrazatricyclo[6.4.0.02,6]dodeca-1(8),2(6),4,9,11-pentaen-3-yl)-2-(hydroxymethyl)oxolan-3-ol
• CAS: 1160725-85-8
• 化学式: C₁₂H₁₃N₅O₃S
• 分子量: 307.333
• InChiKey: JZRWTERULKNICK-RRKCRQDMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  148
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  在 4-二甲氨基吡啶 、 2,4,6-三异丙基苯磺酰氯 、 三氟化硼乙醚 、 三乙胺 、 乙硫醇 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 6.0h， 生成 1-(2-Deoxy-I(2)-D-erythro-pentofuranosyl)-1H-imidazo[4a(2),5a(2):4,5]thieno[3,2-d]pyrimidin-5-amine
  参考文献：
  名称：

  Synthesis and biological evaluation of a series of thieno-expanded tricyclic purine 2′-deoxy nucleoside analogues

  摘要：

  Introducing structural diversity into the nucleoside scaffold for use as potential chemotherapeutics has long been considered an important approach to drug design. In that regard, we have designed and synthesized a number of innovative 2'-deoxy expanded nucleosides where a heteroaromatic thiophene spacer ring has been inserted in between the imidazole and pyrimidine ring systems of the natural purine scaffold. The synthetic efforts towards realizing the expanded 2'-deoxy-guanosine and -adenosine tricyclic analogues as well as the preliminary biological results are presented herein. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.03.004

文献信息

• Synthesis and biological evaluation of a series of thieno-expanded tricyclic purine 2′-deoxy nucleoside analogues
  作者：Orrette R. Wauchope、Cameron Johnson、Pasupathy Krishnamoorthy、Graciela Andrei、Robert Snoeck、Jan Balzarini、Katherine L. Seley-Radtke

  DOI：10.1016/j.bmc.2012.03.004

  日期：2012.5

  Introducing structural diversity into the nucleoside scaffold for use as potential chemotherapeutics has long been considered an important approach to drug design. In that regard, we have designed and synthesized a number of innovative 2'-deoxy expanded nucleosides where a heteroaromatic thiophene spacer ring has been inserted in between the imidazole and pyrimidine ring systems of the natural purine scaffold. The synthetic efforts towards realizing the expanded 2'-deoxy-guanosine and -adenosine tricyclic analogues as well as the preliminary biological results are presented herein. (C) 2012 Elsevier Ltd. All rights reserved.