2,4-dimethoxy-7-(β-D-glycero-pentofuran-3'-ulos-1'-yl)thieno[3,2-d]pyrimidine | 936568-34-2

• 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: 2,4-dimethoxy-7-(β-D-glycero-pentofuran-3'-ulos-1'-yl)thieno[3,2-d]pyrimidine
• 英文别名: (2R,5R)-5-(2,4-dimethoxythieno[3,2-d]pyrimidin-7-yl)-2-(hydroxymethyl)oxolan-3-one
• CAS: 936568-34-2
• 化学式: C₁₃H₁₄N₂O₅S
• 分子量: 310.331
• InChiKey: XRUQKQAVLRVQCM-RKDXNWHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  119
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2,4-dimethoxy-7-(β-D-glycero-pentofuran-3'-ulos-1'-yl)thieno[3,2-d]pyrimidine 在 吡啶 、 三乙酰氧基硼氢化钠 、 溶剂黄146 、 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 20.0h， 生成 1'-β-[7-(thieno[3,2-d]pyrimidin-2,4-dione)]-3',5'-acetoxy-2'-deoxyribofuranose
  参考文献：
  名称：

  Antiproliferative activities of halogenated thieno[3,2-d]pyrimidines

  摘要：

  The in vitro evaluation of thieno[3,2-d]pyrimidines identified halogenated compounds 1 and 2 with antiproliferative activity against three different cancer cell lines. A structure activity relationship study indicated the necessity of the chlorine at the C4-position for biological activity. The two most active compounds 1 and 2 were found to induce apoptosis in the leukemia L1210 cell line. Additionally, the compounds were screened against a variety of other microbial targets and as a result, selective activity against several fungi was also observed. The synthesis and preliminary biological results are reported herein. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.02.033
• 作为产物：
  描述：

  7-bromothieno[3,2-d]pyrimidine-2,4(1H,3H)-dione 在 palladium diacetate 四丁基氯化铵 、 碳酸氢钠 、 N,N-二乙基苯胺 、 三氯氧磷 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 61.0h， 生成 2,4-dimethoxy-7-(β-D-glycero-pentofuran-3'-ulos-1'-yl)thieno[3,2-d]pyrimidine
  参考文献：
  名称：

  设计新的同构荧光核碱基类似物：噻吩并[3,2- d ]嘧啶核

  摘要：

  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。

  DOI：

  10.1016/j.tet.2007.01.075

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。
• Antiproliferative activities of halogenated thieno[3,2-d]pyrimidines
  作者：Kartik W. Temburnikar、Sarah C. Zimmermann、Nathaniel T. Kim、Christina R. Ross、Christopher Gelbmann、Christine E. Salomon、Gerald M. Wilson、Jan Balzarini、Katherine L. Seley-Radtke

  DOI：10.1016/j.bmc.2014.02.033

  日期：2014.4

  The in vitro evaluation of thieno[3,2-d]pyrimidines identified halogenated compounds 1 and 2 with antiproliferative activity against three different cancer cell lines. A structure activity relationship study indicated the necessity of the chlorine at the C4-position for biological activity. The two most active compounds 1 and 2 were found to induce apoptosis in the leukemia L1210 cell line. Additionally, the compounds were screened against a variety of other microbial targets and as a result, selective activity against several fungi was also observed. The synthesis and preliminary biological results are reported herein. (C) 2014 Elsevier Ltd. All rights reserved.