2-methoxy-4-methyl-6-(3-nitrophenyl)-1,5(6H)-pyrimidinedicarboxylic acid 5-(1-methylethyl) 1-(4-nitrophenyl) diester | 123486-12-4

• 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: 2-methoxy-4-methyl-6-(3-nitrophenyl)-1,5(6H)-pyrimidinedicarboxylic acid 5-(1-methylethyl) 1-(4-nitrophenyl) diester
• 英文别名: 2-Methoxy-4-methyl-6(3-nitrophenyl)-1,5(6H)-pyrimidinedicarboxylic acid, 5-(1-methylethyl) 1-(4-nitrophenyl)ester；3-O-(4-nitrophenyl) 5-O-propan-2-yl 2-methoxy-6-methyl-4-(3-nitrophenyl)-4H-pyrimidine-3,5-dicarboxylate
• CAS: 123486-12-4
• 化学式: C₂₃H₂₂N₄O₉
• 分子量: 498.449
• InChiKey: LEJPFHOVFLJKOS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  36
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  169
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2-methoxy-4-methyl-6-(3-nitrophenyl)-1,5(6H)-pyrimidinedicarboxylic acid 5-(1-methylethyl) 1-(4-nitrophenyl) diester 在 盐酸 、 氨 作用下， 以 四氢呋喃 、 甲醇 、 乙腈 为溶剂， 反应 0.5h， 生成 1-(aminocarbonyl)-1,2,3,6-tetrahydro-4-methyl-6-(3-nitrophenyl)-2-oxo-5-pyrimidinecarboxylic acid 1-methylethyl ester
  参考文献：
  名称：

  Substituted 1,4-dihydropyrimidines. 3. Synthesis of selectively functionalized 2-hetero-1,4-dihydropyrimidines

  摘要：

  DOI：

  10.1021/jo00286a020
• 作为产物：
  描述：

  2-[(3-nitrophenyl)methylene]-3-oxobutanoic acid,1-methylethyl ester 在 吡啶 、 碳酸氢钠 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 生成 2-methoxy-4-methyl-6-(3-nitrophenyl)-1,5(6H)-pyrimidinedicarboxylic acid 5-(1-methylethyl) 1-(4-nitrophenyl) diester
  参考文献：
  名称：

  Substituted 1,4-dihydropyrimidines. 3. Synthesis of selectively functionalized 2-hetero-1,4-dihydropyrimidines

  摘要：

  DOI：

  10.1021/jo00286a020

文献信息

• Dihydropyrimidine calcium channel blockers. II. 3-Substituted-4-aryl-1,4-dihydro-6-methyl-5-pyrimidinecarboxylic acid esters as potent mimics of dihydropyridines
  作者：Karnail S. Atwal、George C. Rovnyak、S. David Kimball、David M. Floyd、Suzanne Moreland、Brian N. Swanson、Jack Z. Gougoutas、Joseph Schwartz、Kaye M. Smillie、Mary F. Malley

  DOI：10.1021/jm00171a044

  日期：1990.9

  To enhance the intrinsic potency of dihydropyrimidine calcium channel blockers, we have modified the structure of previously described 2-heteroalkyl-1,4-dihydropyrimidines 2 to 3-substituted 1,4-dihydropyrimidines 3. Structure-activity studies using potassium-depolarized rabbit aorta show that ortho, meta-disubstituted aryl derivatives are more potent than either ortho- or meta-monosubstituted compounds. While vasorelaxant activity was critically dependent on the size of the C5 ester group, isopropyl ester being the best, a variety of substituents (carbamate, acyl, sulfonyl, alkyl) were tolerated at N3. Our results show dihydropyrimidines 3 are significantly more potent than corresponding 2-heteroalkyl-1,4-dihydropyrimidines 2 and only slightly less potent than similarly substituted 2-heteroalkyl-1,4-dihydropyridines 4 and 5. Whereas dihydropyridine enantiomers usually show 10-15-fold difference in activity, the enantiomers of dihydropyrimidine 3j show more than a 1000-fold difference in activity. These results strengthen the requirement of an enamino ester for binding to the dihydropyridine receptor and indicate a nonspecific role for the N3-substituent.
• ATWAL, KARNAIL
  作者：ATWAL, KARNAIL

  DOI：——

  日期：——
• ATWAL, KARNAIL S.;ROVNYAK, GEORGE C.;KIMBALL, S. DAVID;FLOYD, DAVID M.;MO+, J. MED. CHEM., 33,(1990) N, C. 2629-2635
  作者：ATWAL, KARNAIL S.、ROVNYAK, GEORGE C.、KIMBALL, S. DAVID、FLOYD, DAVID M.、MO+

  DOI：——

  日期：——
• Substituted 1,4-dihydropyrimidines. 3. Synthesis of selectively functionalized 2-hetero-1,4-dihydropyrimidines
  作者：Karnail S. Atwal、George C. Rovnyak、Brian C. O'Reilly、Joseph Schwartz

  DOI：10.1021/jo00286a020

  日期：1989.12