3,6-Dihydro-2H-pyridine-1,4-dicarboxylic acid 1-tert-butyl ester 4-(2,2-dimethyl-propionyloxymethyl) ester | 70777-20-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3,6-Dihydro-2H-pyridine-1,4-dicarboxylic acid 1-tert-butyl ester 4-(2,2-dimethyl-propionyloxymethyl) ester
• 英文别名: 1-O-tert-butyl 4-O-(2,2-dimethylpropanoyloxymethyl) 3,6-dihydro-2H-pyridine-1,4-dicarboxylate
• CAS: 70777-20-7
• 化学式: C₁₇H₂₇NO₆
• 分子量: 341.404
• InChiKey: TURWXANDAYKHGQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  82.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,6-Dihydro-2H-pyridine-1,4-dicarboxylic acid 1-tert-butyl ester 4-(2,2-dimethyl-propionyloxymethyl) ester 在 氢溴酸 、 溶剂黄146 作用下， 以 乙酸乙酯 为溶剂， 反应 0.08h， 生成 1,2,3,6-Tetrahydro-pyridine-4-carboxylic acid 2,2-dimethyl-propionyloxymethyl ester; hydrobromide
  参考文献：
  名称：

  Esters of isoguvacine as potential prodrugs

  摘要：

  The syntheses of the methyl ester, butyl ester, (ethoxycarbonyl)methyl ester, and 11 (acyloxy)methyl esters of the potent gamma-aminobutyric acid agonist isoguvacine (1,2,3,6-tetrahydropyridine-4-carboxylic acid) and described. The chemical stability of the esters and their in vitro rates of hydrolysis under approximately physiological conditions by nonspecific esterases from human serum were examined. A selected number of the esters were tested for antagonism of convulsions induced by bicuculline, isoniazide, and by electroschock. While in the compounds showed only weak activities in the bicuculline and isoniazide tests, a good correlation between in vitro rates of enzymatic hydrolysis and the time of onset of the antagonism of the electroschock-induced convulsions could be found.

  DOI：

  10.1021/jm00135a009
• 作为产物：
  描述：

  1,2,3,6-四氢-4-吡啶甲酸盐酸盐 在 potassium carbonate 、 三乙胺 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 32.5h， 生成 3,6-Dihydro-2H-pyridine-1,4-dicarboxylic acid 1-tert-butyl ester 4-(2,2-dimethyl-propionyloxymethyl) ester
  参考文献：
  名称：

  Esters of isoguvacine as potential prodrugs

  摘要：

  The syntheses of the methyl ester, butyl ester, (ethoxycarbonyl)methyl ester, and 11 (acyloxy)methyl esters of the potent gamma-aminobutyric acid agonist isoguvacine (1,2,3,6-tetrahydropyridine-4-carboxylic acid) and described. The chemical stability of the esters and their in vitro rates of hydrolysis under approximately physiological conditions by nonspecific esterases from human serum were examined. A selected number of the esters were tested for antagonism of convulsions induced by bicuculline, isoniazide, and by electroschock. While in the compounds showed only weak activities in the bicuculline and isoniazide tests, a good correlation between in vitro rates of enzymatic hydrolysis and the time of onset of the antagonism of the electroschock-induced convulsions could be found.

  DOI：

  10.1021/jm00135a009

文献信息

• 1,2,3,6-Tetrahydroisonicotinic acid and derivatives thereof, methods and starting products for their preparation, and pharmaceutical compositions containing them.
  申请人：Krogsgaard-Larsen, Povl

  公开号：EP0000167A1

  公开（公告）日：1979-01-10

  1,2,3,6-Tetrahydroisonicotinic acid and derivatives thereof, methods and starting products for their preparation, and pharmaceutical compositions containing them. Compounds of formuta is which R" is hydrogen, acetyl or a group wherein R1 is C1-8 alkyl; phenyl; substituted phenyl, phenylalkyl in which the phenyl group may be substituted. R' is hydrogen; C1-8 alkyl; phenyl; substituted phenyl, phenylalkyl, substituted phenylalkyl or idanyl; or R' is a group wherein R2 and R3 are hydrogen; C1-6 alkyl; or phenylalkyl and R4 designates C1-8 alkyl; phenyl; substituted phenyl or phenylalkyl and salts thereof. Intermediates for preparing (1) are in which Z is hydrogen or a protecting group and W is hydrogen or a readily removable group and saits thereof which are subjected to dehydration and in which Z' and W' have the same meaning as and W and salts thereof, which are reacted with appropriate reagents. The compounds (I) exhibit γ-aminobutyric acid related activity and are useful as active ingredients in pharmaceutical compositions. They may additionally contain a minor tranquilizer or a neuroleptic.

  1,2,3,6-四氢异烟酸及其衍生物、制备它们的方法和起始产品，以及含有它们的药物组合物。化合物 其中 R "是氢、乙酰基或一个基团 其中 R1 是 C1-8 烷基；苯基；取代苯基；苯基烷基，其中苯基可被取代。R'是氢；C1-8 烷基；苯基；取代的苯基、苯基烷基、取代的苯基烷基或偶氮苯基；或 R'是一个基团，其中 R2 和 R3 是氢；C1-6 烷基；或苯基烷基，R4 表示 C1-8 烷基；苯基；取代的苯基或苯基烷基及其盐。制备（1）的中间体有 其中 Z 为氢或保护基，W 为氢或易脱去的基团及其经脱水处理的盐，以及 其中 Z'和 W'的含义与 W 及其盐类相同，它们与适当的试剂反应。 化合物（I）具有与γ-氨基丁酸相关的活性，可用作药物组合物中的活性成分。此外，它们还可能含有轻微的镇静剂或神经安定剂。
• Esters of isoguvacine as potential prodrugs
  作者：Erik Falch、Povl Krogsgaard-Larsen、Anne Vibeke Christensen

  DOI：10.1021/jm00135a009

  日期：1981.3

  The syntheses of the methyl ester, butyl ester, (ethoxycarbonyl)methyl ester, and 11 (acyloxy)methyl esters of the potent gamma-aminobutyric acid agonist isoguvacine (1,2,3,6-tetrahydropyridine-4-carboxylic acid) and described. The chemical stability of the esters and their in vitro rates of hydrolysis under approximately physiological conditions by nonspecific esterases from human serum were examined. A selected number of the esters were tested for antagonism of convulsions induced by bicuculline, isoniazide, and by electroschock. While in the compounds showed only weak activities in the bicuculline and isoniazide tests, a good correlation between in vitro rates of enzymatic hydrolysis and the time of onset of the antagonism of the electroschock-induced convulsions could be found.