5-[(cyclopropylmethoxy)carbonyl]-3-[(heptyloxy)carbonyl]-6-methyl-4-(2-nitrophenyl)-3,4-dihydropyrimidin-2(1H)-one | 110448-23-2

• 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-[(cyclopropylmethoxy)carbonyl]-3-[(heptyloxy)carbonyl]-6-methyl-4-(2-nitrophenyl)-3,4-dihydropyrimidin-2(1H)-one
• 英文别名: 5-O-(cyclopropylmethyl) 3-O-heptyl 6-methyl-4-(2-nitrophenyl)-2-oxo-1,4-dihydropyrimidine-3,5-dicarboxylate
• CAS: 110448-23-2
• 化学式: C₂₄H₃₁N₃O₇
• 分子量: 473.526
• InChiKey: LDAFIPFXCYSJRE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  131
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  氯甲酸正庚酯 在 盐酸 、 sodium hydride 作用下， 以 氯仿 为溶剂， 反应 2.67h， 生成 5-[(cyclopropylmethoxy)carbonyl]-3-[(heptyloxy)carbonyl]-6-methyl-4-(2-nitrophenyl)-3,4-dihydropyrimidin-2(1H)-one
  参考文献：
  名称：

  Dihydropyrimidines: novel calcium antagonists with potent and long-lasting vasodilative and anti-hypertensive activity

  摘要：

  The novel calcium antagonists 3-N-substituted-3,4-dihydropyrimidines 1 and 9 and 3-N-substituted-dihydro-pyrimidin-2(1H)-ones 8 were regioselectively synthesized in good yields. Compounds 1 [especially 1s [R1 = (CH2)2N(benzyl)(2-naphthylmethyl), R2 = i-Pr, X = 0-NO2] and 1t [R1 = (CH2)2N(benzyl)(3,4-dichlorobenzyl), R2 = i-Pr, X = 0-NO2]] exhibited not only more potent and longer lasting vasodilative action but also a hypotensive activity with slow onset as compared with dihydropyridines. Moreover, some dihydropyrimidines [1q [R1 = (CH2)2N(benzyl)(3-phenylpropyl), R2 = CH2(cyclopropyl), X = 0-NO2], 1s, and 1t] were weaker in blocking atrioventricular conduction in anesthetized open-chest dogs and less toxic than the dihydropyridines.

  DOI：

  10.1021/jm00130a029

文献信息

• Regioselective synthesis of N-substituted dihydropyrimidin-2(1H) or (3H)-one
  作者：Hidetsura Cho、Yumi Takeuchi、Masaru Ueda、Akira Mizuno

  DOI：10.1016/s0040-4039(00)82880-4

  日期：——
• CHO, HIDETSURA;UEDA, MASARU;SHIMA, KEIYUU;MIZUNO, AKIRA;HAYASHIMATSU, MAR+, J. MED. CHEM., 32,(1989) N0, C. 2399-2406
  作者：CHO, HIDETSURA、UEDA, MASARU、SHIMA, KEIYUU、MIZUNO, AKIRA、HAYASHIMATSU, MAR+

  DOI：——

  日期：——
• CHO, HIDETSURA;TAKEUCHI, YUMI;UEDA, MASARU;MIZUNO, AKIRA, TETRAHEDRON LETT., 29,(1988) N 42, C. 5405-5408
  作者：CHO, HIDETSURA、TAKEUCHI, YUMI、UEDA, MASARU、MIZUNO, AKIRA

  DOI：——

  日期：——
• Dihydropyrimidines: novel calcium antagonists with potent and long-lasting vasodilative and anti-hypertensive activity
  作者：Hidetsura Cho、Masaru Ueda、Keiyuu Shima、Akira Mizuno、Mariko Hayashimatsu、Yoshiko Ohnaka、Yumi Takeuchi、Mikiko Hamaguchi、Kazuo Aisaka

  DOI：10.1021/jm00130a029

  日期：1989.10

  The novel calcium antagonists 3-N-substituted-3,4-dihydropyrimidines 1 and 9 and 3-N-substituted-dihydro-pyrimidin-2(1H)-ones 8 were regioselectively synthesized in good yields. Compounds 1 [especially 1s [R1 = (CH2)2N(benzyl)(2-naphthylmethyl), R2 = i-Pr, X = 0-NO2] and 1t [R1 = (CH2)2N(benzyl)(3,4-dichlorobenzyl), R2 = i-Pr, X = 0-NO2]] exhibited not only more potent and longer lasting vasodilative action but also a hypotensive activity with slow onset as compared with dihydropyridines. Moreover, some dihydropyrimidines [1q [R1 = (CH2)2N(benzyl)(3-phenylpropyl), R2 = CH2(cyclopropyl), X = 0-NO2], 1s, and 1t] were weaker in blocking atrioventricular conduction in anesthetized open-chest dogs and less toxic than the dihydropyridines.