1-(2-deoxy-β-D-erythropentosyl)thieno<3,2-d>pyrimidine-2,4-dione | 160234-48-0

• 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-β-D-erythropentosyl)thieno<3,2-d>pyrimidine-2,4-dione
• 英文别名: 1-(2-deoxy-β-D-erythropentosyl)thieno[3,2-d]pyrimidine-2,4-dione；1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]thieno[3,2-d]pyrimidine-2,4-dione
• CAS: 160234-48-0
• 化学式: C₁₁H₁₂N₂O₅S
• 分子量: 284.293
• InChiKey: GKHQERGLQPKJQH-XLPZGREQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  127
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(2-deoxy-β-D-erythropentosyl)thieno<3,2-d>pyrimidine-2,4-dione 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 反应 26.25h， 生成 2,3'-anhydro-1-(2-deoxy-5-O-methanesulfonyl-β-D-threo-pentofuranosyl)thieno<3,2-d>pyrimidin-4-one
  参考文献：
  名称：

  Synthesis of N-1β-D-Arabinofuranosyl and N-1-2′-Deoxy-β-D-erythro-pentofuranosyl Thieno [3,2-d] Pyrimidine Nucleosides

  摘要：

  Synthetic methods for 1-(beta-D-arabinofuranosyl) and 1(2-deoxy-beta-D-erythro-pentofuranosyl)thieno[3,2-d]pyrimidine-2,4-diones from the corresponding 1-(beta-D-ribofuranosyl) nucleoside have been developed in this report. These compounds were tested against HIV-1 in CEM cl 13 cell cultures, but none df them exhibited significant inhibitory activity against this virus.

  DOI：

  10.1080/15257779408011866
• 作为产物：
  描述：

  1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)thieno<3,2-d>pyrimidine-2,4-dione 在 咪唑 、 偶氮二异丁腈 、 四丁基氟化铵 、 氨 、 三正丁基氢锡 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 78.0h， 生成 1-(2-deoxy-β-D-erythropentosyl)thieno<3,2-d>pyrimidine-2,4-dione
  参考文献：
  名称：

  Synthesis of N-1β-D-Arabinofuranosyl and N-1-2′-Deoxy-β-D-erythro-pentofuranosyl Thieno [3,2-d] Pyrimidine Nucleosides

  摘要：

  Synthetic methods for 1-(beta-D-arabinofuranosyl) and 1(2-deoxy-beta-D-erythro-pentofuranosyl)thieno[3,2-d]pyrimidine-2,4-diones from the corresponding 1-(beta-D-ribofuranosyl) nucleoside have been developed in this report. These compounds were tested against HIV-1 in CEM cl 13 cell cultures, but none df them exhibited significant inhibitory activity against this virus.

  DOI：

  10.1080/15257779408011866

文献信息

• Designing new isomorphic fluorescent nucleobase analogues: the thieno[3,2-d]pyrimidine core
  作者：Yitzhak Tor、Susan Del Valle、David Jaramillo、Seergazhi G. Srivatsan、Andro Rios、Haim Weizman

  DOI：10.1016/j.tet.2007.01.075

  日期：2007.4

  thieno[3,2-d]pyrimidine-2,4(1H,3H)-dione that serves as a core heterocycle. This condensed pyrimidine is converted into an emissive pyrimidine nucleoside analogue by N-glycosylation and into an emissive purine nucleoside analogue by C-glycosidation at the thiophene's beta position. The design principles of this archetypical system are outlined together with the syntheses and photophysical properties of the

  描述了一种用于荧光核苷家族的收敛方法。它依赖于作为核心杂环的噻吩并[3,2 - d ]嘧啶-2,4（1 H，3 H）-二酮。该缩合的嘧啶通过N-糖基化转化为发光的嘧啶核苷类似物，并通过噻吩的β位上的C-糖基化转化为发光的嘌呤核苷类似物。概述了该原型系统的设计原理以及所得核苷的合成和光物理性质。