5-(2-cyanoethoxycarbonyl)-1,6-dihydro-2-methoxy-4-methyl-6-(4-nitrophenyl)-1-[(4-nitrophenyloxy)carbonyl]pyrimidine | 251930-33-3

• 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: 5-(2-cyanoethoxycarbonyl)-1,6-dihydro-2-methoxy-4-methyl-6-(4-nitrophenyl)-1-[(4-nitrophenyloxy)carbonyl]pyrimidine
• 英文别名: 5-O-(2-cyanoethyl) 3-O-(4-nitrophenyl) 2-methoxy-6-methyl-4-(4-nitrophenyl)-4H-pyrimidine-3,5-dicarboxylate
• CAS: 251930-33-3
• 化学式: C₂₃H₁₉N₅O₉
• 分子量: 509.432
• InChiKey: CYHJJXKBVMLLSH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  193
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  5-(2-cyanoethoxycarbonyl)-1,6-dihydro-2-methoxy-4-methyl-6-(4-nitrophenyl)-1-[(4-nitrophenyloxy)carbonyl]pyrimidine 在 盐酸 、 sodium hydroxide 、 potassium carbonate 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 3.0h， 生成 3-[3-(4-Methoxycarbonyl-4-phenyl-piperidin-1-yl)-propylcarbamoyl]-6-methyl-4-(4-nitro-phenyl)-2-oxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid
  参考文献：
  名称：

  Design and Synthesis of Novel α_1a Adrenoceptor-Selective Antagonists. 1. Structure−Activity Relationship in Dihydropyrimidinones

  摘要：

  Dihydropyrimidinones such as compound 12 exhibited high binding affinity and subtype selectivity for the cloned human alpha(1a) receptor. Systematic modifications of 12 led to identification of highly potent and subtype-selective compounds such as (+)-30 and (+)-103, with high binding affinity (K-i = 0.2 nM) for alpha(1a) receptor and greater than 1500-fold selectivity over alpha(1b) and alpha(1d) adrenoceptors. The compounds were found to be functional antagonists in human, rat, and dog prostate tissues. Compound (+)-103 exhibited excellent selectively to inhibit intraurethral pressure (IUP) as compared to lowering diastolic blood pressure (DBP) in mongrel dogs (K-b(DBP)/K-b(IUP) = 40) suggesting uroselectivity for alpha(1a)-selective compounds.

  DOI：

  10.1021/jm990200p
• 作为产物：
  描述：

  2-cyanoethyl 2-acetyl-3-(4-nitrophenyl)-2-propenoate 在 碳酸氢钠 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 15.0h， 生成 5-(2-cyanoethoxycarbonyl)-1,6-dihydro-2-methoxy-4-methyl-6-(4-nitrophenyl)-1-[(4-nitrophenyloxy)carbonyl]pyrimidine
  参考文献：
  名称：

  Design and Synthesis of Novel α_1a Adrenoceptor-Selective Antagonists. 1. Structure−Activity Relationship in Dihydropyrimidinones

  摘要：

  Dihydropyrimidinones such as compound 12 exhibited high binding affinity and subtype selectivity for the cloned human alpha(1a) receptor. Systematic modifications of 12 led to identification of highly potent and subtype-selective compounds such as (+)-30 and (+)-103, with high binding affinity (K-i = 0.2 nM) for alpha(1a) receptor and greater than 1500-fold selectivity over alpha(1b) and alpha(1d) adrenoceptors. The compounds were found to be functional antagonists in human, rat, and dog prostate tissues. Compound (+)-103 exhibited excellent selectively to inhibit intraurethral pressure (IUP) as compared to lowering diastolic blood pressure (DBP) in mongrel dogs (K-b(DBP)/K-b(IUP) = 40) suggesting uroselectivity for alpha(1a)-selective compounds.

  DOI：

  10.1021/jm990200p