{4-[(E)-2-(5-Nitro-2,6-dioxo-1,3-dipropyl-1,2,3,6-tetrahydro-pyrimidin-4-yl)-vinyl]-phenoxy}-phenyl-acetic acid | 875802-11-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮
• 英文名称: {4-[(E)-2-(5-Nitro-2,6-dioxo-1,3-dipropyl-1,2,3,6-tetrahydro-pyrimidin-4-yl)-vinyl]-phenoxy}-phenyl-acetic acid
• CAS: 875802-11-2
• 化学式: C₂₆H₂₇N₃O₇
• 分子量: 493.516
• InChiKey: YHUFISIIBVZQPW-NTCAYCPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.11
• 重原子数：
  36.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  133.67
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  {4-[(E)-2-(5-Nitro-2,6-dioxo-1,3-dipropyl-1,2,3,6-tetrahydro-pyrimidin-4-yl)-vinyl]-phenoxy}-phenyl-acetic acid 在 甲酸 、 sodium dithionite 、 polymer-bound morpholine 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-[4-(2,4-dioxo-1,3-dipropyl-5H-pyrrolo[3,2-d]pyrimidin-6-yl)phenoxy]-N,2-diphenylacetamide
  参考文献：
  名称：

  Design, Synthesis, and Structure−Activity Relationships of 1-,3-,8-, and 9-Substituted-9-deazaxanthines at the Human A_2B Adenosine Receptor

  摘要：

  Over two hundred 1-, 3-, 8-, and 9-substituted-9-deazaxanthines were prepared and evaluated for their binding affinity at the recombinant human adenosine receptors, in particular at the hA(2B) and hA(2A) subtypes. Several ligands endowed with sub-micromolar to low nanomolar binding affinity at hA(2B) receptors, good selectivity over hA(2A) and hA(3), but a relatively poor selectivity over hA(1) were obtained. Good antagonistic potencies and efficacies, with pA(2) values close to the corresponding pK(i)s, were observed in functional assays in vitro performed on a selected series of compounds. 1,3-Dimethyl-8-phenoxy-(N-p-halogenophenyl)-acetamido-9-deazaxanthine derivatives appeared as the most interesting leads, some of them showing outstanding hA(2B) affinities, high selectivity over hA(2A) and hA(3), but low selectivity over hA(1). Structure-affinity relationships suggested that the binding potency at the hA(2B) receptor was mainly modulated by the steric (lipophilic) properties of the substituents at positions 1 and 3 and by the electronic and lipophilic characteristics of the substituents at position 8. A comparison among affinity and selectivity profiles of 9-deazaxanthines with the corresponding xanthines suggested some possible differences in their binding mode.

  DOI：

  10.1021/jm0506221
• 作为产物：
  描述：

  2-(4-醛基苯氧基)-2-苯基乙酸 、 6-methyl-5-nitro-1,3-dipropyl-1H-pyrimidine-2,4-dione 在 哌啶 作用下， 以 1,4-二氧六环 为溶剂， 生成 {4-[(E)-2-(5-Nitro-2,6-dioxo-1,3-dipropyl-1,2,3,6-tetrahydro-pyrimidin-4-yl)-vinyl]-phenoxy}-phenyl-acetic acid
  参考文献：
  名称：

  Design, Synthesis, and Structure−Activity Relationships of 1-,3-,8-, and 9-Substituted-9-deazaxanthines at the Human A_2B Adenosine Receptor

  摘要：

  Over two hundred 1-, 3-, 8-, and 9-substituted-9-deazaxanthines were prepared and evaluated for their binding affinity at the recombinant human adenosine receptors, in particular at the hA(2B) and hA(2A) subtypes. Several ligands endowed with sub-micromolar to low nanomolar binding affinity at hA(2B) receptors, good selectivity over hA(2A) and hA(3), but a relatively poor selectivity over hA(1) were obtained. Good antagonistic potencies and efficacies, with pA(2) values close to the corresponding pK(i)s, were observed in functional assays in vitro performed on a selected series of compounds. 1,3-Dimethyl-8-phenoxy-(N-p-halogenophenyl)-acetamido-9-deazaxanthine derivatives appeared as the most interesting leads, some of them showing outstanding hA(2B) affinities, high selectivity over hA(2A) and hA(3), but low selectivity over hA(1). Structure-affinity relationships suggested that the binding potency at the hA(2B) receptor was mainly modulated by the steric (lipophilic) properties of the substituents at positions 1 and 3 and by the electronic and lipophilic characteristics of the substituents at position 8. A comparison among affinity and selectivity profiles of 9-deazaxanthines with the corresponding xanthines suggested some possible differences in their binding mode.

  DOI：

  10.1021/jm0506221