1-<<<4-(2,3-dichlorophenyl)-3-(ethoxycarbonyl)-5-(methoxycarbonyl)-6-methyl-1,4-dihydropyridin-2-yl>methoxy>acetyl>thiosemicarbazide | 90445-10-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 1-<<<4-(2,3-dichlorophenyl)-3-(ethoxycarbonyl)-5-(methoxycarbonyl)-6-methyl-1,4-dihydropyridin-2-yl>methoxy>acetyl>thiosemicarbazide
• 英文别名: 1-<2-{[4-(2,3-dichlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridin-2-yl]methoxy}acetyl>thiosemicarbazide；1-({[4-(2,3-dichlorophenyl)-3-(ethoxycarbonyl)-5-(methoxycarbonyl)-6-methyl-1,4-dihydropyridin-2-yl]methoxy}acetyl)thiosemicarbazide；3-O-ethyl 5-O-methyl 2-[[2-(2-carbamothioylhydrazinyl)-2-oxoethoxy]methyl]-4-(2,3-dichlorophenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate
• CAS: 90445-10-6
• 化学式: C₂₁H₂₄Cl₂N₄O₆S
• 分子量: 531.417
• InChiKey: COCAOZAFJWSRGX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.83
• 重原子数：
  34.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  141.01
• 氢给体数：
  4.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  1-<<<4-(2,3-dichlorophenyl)-3-(ethoxycarbonyl)-5-(methoxycarbonyl)-6-methyl-1,4-dihydropyridin-2-yl>methoxy>acetyl>thiosemicarbazide 以 正己烷 、 二氯甲烷 、 三氯氧磷 为溶剂， 生成 5-Amino-2-{[4-(2,3-dichlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridin-2-yl]methoxymethyl}-1,3,4-thiadiazole
  参考文献：
  名称：

  Dihydropyridine anti-ischaemic and antihypertensive agents

  摘要：

  1,4-二氢吡啶衍生物的化学式为：其中R为芳基或杂环芳基；R.sup.1和R.sup.2分别独立为C.sub.1-C.sub.4烷基或2-甲氧基乙基；Y为--(CH.sub.2).sub.n --，--CH.sub.2 CH(CH.sub.3)--或--CH.sub.2 C(CH.sub.3).sub.2 ；n为1至3；X为含有5或6个成员的氮含杂环芳香环，可能可选地被一个或多个C.sub.1-C.sub.4烷基，苯基，苄基，CN，--N(R.sup.3).sub.2，(CH.sub.2).sub.m CO.sub.2 H，(CH.sub.2).sub.m CO.sub.2 (C.sub.1-C.sub.4烷基)或(CH.sub.2).sub.m CON(R.sup.3).sub.2基团取代；其中每个R.sup.3独立地为H或C.sub.1-C.sub.4烷基，m为0或1；以及它们的药学上可接受的酸盐，以及含有这些化合物的药物制剂，具有作为抗缺血和降压药物的用途。

  公开号：

  US04515799A1
• 作为产物：
  描述：

  ethyl 4-<(methoxycarbonyl)methoxy>acetoacetate 在 sodium hydroxide 、 N,N'-羰基二咪唑 作用下， 反应 24.5h， 生成 1-<<<4-(2,3-dichlorophenyl)-3-(ethoxycarbonyl)-5-(methoxycarbonyl)-6-methyl-1,4-dihydropyridin-2-yl>methoxy>acetyl>thiosemicarbazide
  参考文献：
  名称：

  Long-acting dihydropyridine calcium antagonists. 3. Synthesis and structure-activity relationships for a series of 2-[(heterocyclylmethoxy)methyl] derivatives

  摘要：

  The preparation of 1,4-dihydropyridines containing (heterocyclylmethoxy)methyl groups in the 2-position is described and the structural identification of certain of the compounds using 1H NMR spectroscopic methods is reported. The calcium antagonist activity of the compounds on rat aorta is listed and is compared with the negative inotropic potency as determined by using a Langendorff-perfused guinea pig heart model. Several compounds are more potent than nifedipine and show greater selectivity for the vasculature over the heart. One compound, 2-[(2-amino-4-hydroxypyrimidin-6-yl)methoxy]-4- (2,3-dichlorophenyl)-3-(ethoxycarbonyl)-5-(methoxycarbonyl)-6-methyl- 1,4-dihydropyridine (27, UK-56,593), was identified as a potent (IC50 = 1.6 x 10(-9) M), tissue-selective calcium antagonist which proved to have a markedly longer duration of action (greater than 4.5 h) than nifedipine in the anesthetized dog on intravenous administration.

  DOI：

  10.1021/jm00130a026

文献信息

• ALKER, DAVID;CAMPBELL, SIMON F.;CROSS, PETER E.;BURGES, ROGER A.;CARTER, +, J. MED. CHEM., 32,(1989) N0, C. 2381-2388
  作者：ALKER, DAVID、CAMPBELL, SIMON F.、CROSS, PETER E.、BURGES, ROGER A.、CARTER, +

  DOI：——

  日期：——