1,3-dimethyl-5-nitro-6-[(E)-2-(thien-2-yl)-vinyl]-pyrimidine-2,4(1H,3H)-dione

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 1,3-dimethyl-5-nitro-6-[(E)-2-(thien-2-yl)-vinyl]-pyrimidine-2,4(1H,3H)-dione
• 英文别名: 1,3-dimethyl-5-nitro-6-[(E)-2-(thiophen-2-yl)ethenyl]pyrimidine-2,4(1H,3H)-dione；1,3-dimethyl-5-nitro-6-[(E)-2-thiophen-2-ylethenyl]pyrimidine-2,4-dione
• 化学式: C₁₂H₁₁N₃O₄S
• 分子量: 293.303
• InChiKey: QUGSBXRCIFAORV-AATRIKPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  115
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,3-dimethyl-5-nitro-6-[(E)-2-(thien-2-yl)-vinyl]-pyrimidine-2,4(1H,3H)-dione 在 亚磷酸三乙酯 作用下， 反应 7.0h， 以22%的产率得到1,3-Dimethyl-6-thiophen-2-yl-1,5-dihydro-pyrrolo[3,2-d]pyrimidine-2,4-dione
  参考文献：
  名称：

  8-Substituted-9-deazaxanthines as adenosine receptor ligands: design, synthesis and structure-affinity relationships at A2B

  摘要：

  A number of 8-substituted-9-deazaxanthine derivatives (1,3-dialkyl-6-substituted-1H-pyrrolo[3,2-d]pyrimidine-2,4(3H,5H)-diones) were prepared and tested for their antagonistic activity at the recombinant human adenosine receptors, in particular at the A(2B) and A(2A) receptor subtypes. Compounds endowed with micromolar to nanomolar binding affinities, but with poor A(2B)/A(2A) selectivity, were obtained. Preliminary quantitative structure-affinity relationships suggested that the binding potency at the A(2B) receptor is mainly modulated by the electronic and lipophilic properties of the ligands. (C) 2004 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2004.07.008
• 作为产物：
  描述：

  2-噻吩甲醛 、 1,3,6-三甲基-5-硝基-2,4(1H,3H)-嘧啶二酮 在 哌啶 作用下， 以 1,4-二氧六环 为溶剂， 以53%的产率得到1,3-dimethyl-5-nitro-6-[(E)-2-(thien-2-yl)-vinyl]-pyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  8-Substituted-9-deazaxanthines as adenosine receptor ligands: design, synthesis and structure-affinity relationships at A2B

  摘要：

  A number of 8-substituted-9-deazaxanthine derivatives (1,3-dialkyl-6-substituted-1H-pyrrolo[3,2-d]pyrimidine-2,4(3H,5H)-diones) were prepared and tested for their antagonistic activity at the recombinant human adenosine receptors, in particular at the A(2B) and A(2A) receptor subtypes. Compounds endowed with micromolar to nanomolar binding affinities, but with poor A(2B)/A(2A) selectivity, were obtained. Preliminary quantitative structure-affinity relationships suggested that the binding potency at the A(2B) receptor is mainly modulated by the electronic and lipophilic properties of the ligands. (C) 2004 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2004.07.008