1'-β-[7-(2,4-dimethoxythieno[3,2-d]pyrimidine)]-3',5'-acetoxy-2'-deoxyribofuranose | 1591748-66-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1'-β-[7-(2,4-dimethoxythieno[3,2-d]pyrimidine)]-3',5'-acetoxy-2'-deoxyribofuranose
• 英文别名: [(2R,3S,5R)-3-acetyloxy-5-(2,4-dimethoxythieno[3,2-d]pyrimidin-7-yl)oxolan-2-yl]methyl acetate
• CAS: 1591748-66-1
• 化学式: C₁₇H₂₀N₂O₇S
• 分子量: 396.421
• InChiKey: JOALXARXJKTADX-FRRDWIJNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  134
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1'-β-[7-(2,4-dimethoxythieno[3,2-d]pyrimidine)]-3',5'-acetoxy-2'-deoxyribofuranose 在 溶剂黄146 、 sodium iodide 作用下， 反应 3.0h， 以95%的产率得到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 吡啶 、 4-二甲氨基吡啶 、 四丁基氯化铵 、 palladium diacetate 、 三乙酰氧基硼氢化钠 、 碳酸氢钠 、 溶剂黄146 、 三氯氧磷 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 83.0h， 生成 1'-β-[7-(2,4-dimethoxythieno[3,2-d]pyrimidine)]-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

文献信息

• 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.