2-amino-7-(3,3-bishydroxymethylcyclobut-1-yl)-(3H,7H)-pyrrolo<2,3-d>pyrimidin-4-one | 138420-47-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并嘧啶类
• 英文名称: 2-amino-7-(3,3-bishydroxymethylcyclobut-1-yl)-(3H,7H)-pyrrolo<2,3-d>pyrimidin-4-one
• 英文别名: 2-Amino-7-(3,3-bishydroxymethylcyclobut-1-yl)-(3H,7H)-pyrrolo(2,3-d)pyrimidin-4-one；2-amino-7-[3,3-bis(hydroxymethyl)cyclobutyl]-3H-pyrrolo[2,3-d]pyrimidin-4-one
• CAS: 138420-47-0
• 化学式: C₁₂H₁₆N₄O₃
• 分子量: 264.284
• InChiKey: ZUHBBCQMRSQBKI-UHFFFAOYSA-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：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  113
• 氢给体数：
  4
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4,6-二氯-5-(2,2-二乙氧基乙基)嘧啶-2-胺 在 盐酸 、 三氯化硼 、 三乙胺 作用下， 以 二氯甲烷 、 正丁醇 为溶剂， 反应 84.0h， 生成 2-amino-7-(3,3-bishydroxymethylcyclobut-1-yl)-(3H,7H)-pyrrolo<2,3-d>pyrimidin-4-one
  参考文献：
  名称：

  New cyclobutyl analogs of nucleosides. Part 2. Synthesis and antiviral evaluation of 2-amino-7-[3,3-bis (hydroxymethyl)cyclobut-1-yl]-3H,7H-pyrrolo-[2,3-d]pyrimidin-4-one and of cyclobutyl analogs of the pyrimidine nucleosides

  摘要：

  The synthesis and antiviral evaluation of a series of 3,3-dihydroxymethyl cyclobutane nucleoside analogs related to the natural anti-HIV nucleoside, oxetanocin A are reported. The different purine and pyrimidine nucleoside analogs described in this paper have been obtained from 1-amino-3,3-dibenzyloxymethylcyclobutane. The compounds were tested against HSV-1, HCMV and HIV-1 in cell cultures, but none of them exhibited activity against these viruses. These results suggest the crucial role of the position of both hydroxymethyl groups in oxetanocin A and oxetanocin G for antiviral activity.

  DOI：

  10.1016/0223-5234(91)90196-t

文献信息

• New cyclobutyl analogs of nucleosides. Part 2. Synthesis and antiviral evaluation of 2-amino-7-[3,3-bis (hydroxymethyl)cyclobut-1-yl]-3H,7H-pyrrolo-[2,3-d]pyrimidin-4-one and of cyclobutyl analogs of the pyrimidine nucleosides
  作者：H Boumchita、M Legraverend、A Zerial、M Lemaitre、C Huel、E Bisagni

  DOI：10.1016/0223-5234(91)90196-t

  日期：1991.9

  The synthesis and antiviral evaluation of a series of 3,3-dihydroxymethyl cyclobutane nucleoside analogs related to the natural anti-HIV nucleoside, oxetanocin A are reported. The different purine and pyrimidine nucleoside analogs described in this paper have been obtained from 1-amino-3,3-dibenzyloxymethylcyclobutane. The compounds were tested against HSV-1, HCMV and HIV-1 in cell cultures, but none of them exhibited activity against these viruses. These results suggest the crucial role of the position of both hydroxymethyl groups in oxetanocin A and oxetanocin G for antiviral activity.