N-[6-(benzyloxy)-2-(propylsulfanyl)pyrimidin-4-yl]acetamide | 1013029-47-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-[6-(benzyloxy)-2-(propylsulfanyl)pyrimidin-4-yl]acetamide
• 英文别名: N-(6-phenylmethoxy-2-propylsulfanylpyrimidin-4-yl)acetamide
• CAS: 1013029-47-4
• 化学式: C₁₆H₁₉N₃O₂S
• 分子量: 317.412
• InChiKey: GACMOWSTZKJISX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  89.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  6-amino-2-(propylsulfanyl)pyrimidin-4(3H)-one 在 硫酸 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 N-[6-(benzyloxy)-2-(propylsulfanyl)pyrimidin-4-yl]acetamide
  参考文献：
  名称：

  对映体4-酰基氨基-6-烷氧基-2烷硫基嘧啶作为潜在的A3腺苷受体拮抗剂：HPLC手性拆分和全套手性光谱法的绝对构型分配

  摘要：

  三种潜在的A 3腺苷受体拮抗剂的对映体对的手性分离：（R / S）-N-（6-（1-苯乙氧基）-2-（丙硫基）嘧啶-4-基）乙酰胺（1），（R / S）-N-（2-（1-苯乙硫基）-6-丙氧基嘧啶-4-基）乙酰胺（2）和（R / S）-N-（2-（苄硫基）-6-仲丁氧基嘧啶- 4-基）乙酰胺（3）是通过高效液相色谱（HPLC）实现的。三种类型的手性光谱学，即旋光色散（ORD），电子圆二色性（ECD）和振动圆二色性（VCD），被用于对映体化合物。通过与密度泛函理论（DFT）的计算比较，包括广泛的构象分析，获得了三组化合物的绝对构型（AC）的完全分配。手性28：434–440，2016。©2016 Wiley Periodicals，Inc.

  DOI：

  10.1002/chir.22599

文献信息

• Derivatives of 4-Amino-6-hydroxy-2-mercaptopyrimidine as Novel, Potent, and Selective A₃ Adenosine Receptor Antagonists
  作者：Barbara Cosimelli、Giovanni Greco、Marina Ehlardo、Ettore Novellino、Federico Da Settimo、Sabrina Taliani、Concettina La Motta、Marusca Bellandi、Tiziano Tuccinardi、Adriano Martinelli、Osele Ciampi、Maria Letizia Trincavelli、Claudia Martini

  DOI：10.1021/jm701159t

  日期：2008.3.1

  A number of derivatives of 4-amino-6-hydroxy-2-mercaptopyrimidine (5) were synthesized and biologically evaluated as A(3) adenosine receptor (A(3) AR) antagonists. The new compounds were designed as open chain analogues of a triazolopyrimidinone derivative displaying submicromolar affinity for the A3 AR, which had been previously identified using a 3D database search. Substituents R, R', and R" attached to the parent compound 5 were chosen according to factorial design and stepwise lead optimization approaches, taking into account the essentially hydrophobic nature of the A3 AR binding site. As a result, 5m (R = n-C3H7, R' = 4-ClC6H4CH2, R" = CH3) was identified among the pyrimidine derivatives as the ligand featuring the best combination of potency and selectivity for the target receptor. This compound binds to the A3 AR with a K-i of 3.5 nM and is devoid of appreciable affinity for the A(1), A(2A), and A(2B) ARs.
• Enantiomeric 4-Acylamino-6-alkyloxy-2 Alkylthiopyrimidines As Potential A₃Adenosine Receptor Antagonists: HPLC Chiral Resolution and Absolute Configuration Assignment by a Full Set of Chiroptical Spectroscopy
  作者：Daniela Rossi、Rita Nasti、Annamaria Marra、Silvia Meneghini、Giuseppe Mazzeo、Giovanna Longhi、Maurizio Memo、Barbara Cosimelli、Giovanni Greco、Ettore Novellino、Federico Da Settimo、Claudia Martini、Sabrina Taliani、Sergio Abbate、Simona Collina

  DOI：10.1002/chir.22599

  日期：2016.5

  types of chiroptical spectroscopies, namely, optical rotatory dispersion (ORD), electronic circular dichroism (ECD), and vibrational circular dichroism (VCD), were applied to enantiomeric compounds. Through comparison with Density Functional Theory (DFT) calculations, encompassing extensive conformational analysis, full assignment of the absolute configuration (AC) for the three sets of compounds was obtained

  三种潜在的A 3腺苷受体拮抗剂的对映体对的手性分离：（R / S）-N-（6-（1-苯乙氧基）-2-（丙硫基）嘧啶-4-基）乙酰胺（1），（R / S）-N-（2-（1-苯乙硫基）-6-丙氧基嘧啶-4-基）乙酰胺（2）和（R / S）-N-（2-（苄硫基）-6-仲丁氧基嘧啶- 4-基）乙酰胺（3）是通过高效液相色谱（HPLC）实现的。三种类型的手性光谱学，即旋光色散（ORD），电子圆二色性（ECD）和振动圆二色性（VCD），被用于对映体化合物。通过与密度泛函理论（DFT）的计算比较，包括广泛的构象分析，获得了三组化合物的绝对构型（AC）的完全分配。手性28：434–440，2016。©2016 Wiley Periodicals，Inc.