1-((3aR,4R,6R,6aR)-6-Hydroxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-5-phenyl-1H-pyrimidine-2,4-dione | 75759-65-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1-((3aR,4R,6R,6aR)-6-Hydroxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-5-phenyl-1H-pyrimidine-2,4-dione
• CAS: 75759-65-8
• 化学式: C₁₈H₂₀N₂O₆
• 分子量: 360.367
• InChiKey: PBCNYQFZGHZRPF-IXYNUQLISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.61
• 重原子数：
  26.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  102.78
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  1-((3aR,4R,6R,6aR)-6-Hydroxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-5-phenyl-1H-pyrimidine-2,4-dione 在 甲酸 作用下， 以41%的产率得到5-phenyluridine
  参考文献：
  名称：

  用光化学方法简单合成荧光尿苷

  摘要：

  通过2'，3'-0-异亚丙基-5-碘尿苷与pyr的光反应制备了强荧光的5-吡啶基尿苷。通过类似的方法合成了尿嘧啶的几种荧光类似物。

  DOI：

  10.1016/s0040-4039(00)78614-x
• 作为产物：
  描述：

  5-iodo-2',3'-O isopropylidene-uridine 、 苯硼酸 在 trisodium tris(3-sulfophenyl)phosphine 、 palladium diacetate 、 sodium carbonate 作用下， 以 水 、 乙腈 为溶剂， 反应 3.0h， 以56%的产率得到1-((3aR,4R,6R,6aR)-6-Hydroxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-5-phenyl-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Synthesis and structure–activity relationship of uracil nucleotide derivatives towards the identification of human P2Y 6 receptor antagonists

  摘要：

  P2Y(6) receptor (P2Y(6)-R) is involved in various physiological and pathophysiological events. With a view to set rules for the design of UDP-based reversible P2Y(6)-R antagonists as potential drugs, we established structure-activity relationship of UDP analogues, bearing modifications at the uracil ring, ribose moiety, and the phosphate chain. For instance, C5-phenyl- or 3-NMe-uridine-5'-alpha,beta-methylene-diphosphonate, 16 and 23, or lack of 2'-OH, in 12-15, resulted in loss of both agonist and antagonist activity toward hP2Y(6)-R. However, uridylyl phosphosulfate, 19, selectively inhibited hP2Y(6)-R (IC50 112 mu M) versus P2Y(2)/(4)-Rs. In summary, we have established a comprehensive SAR for hP2Y(6)-R ligands towards the development of hP2Y(6)-R antagonists. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.07.004