β-amino-γ-methylthiocrotonic acid ethyl ester | 140171-91-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: β-amino-γ-methylthiocrotonic acid ethyl ester
• 英文别名: ethyl (Z)-3-amino-4-methylsulfanylbut-2-enoate
• CAS: 140171-91-1
• 化学式: C₇H₁₃NO₂S
• 分子量: 175.252
• InChiKey: KBKDAPBTGIYBHY-XQRVVYSFSA-N

物化性质

• 沸点：
  309.3±37.0 °C(Predicted)
• 密度：
  1.104±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  77.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  β-amino-γ-methylthiocrotonic acid ethyl ester 在 甲胺 作用下， 生成 2-(2-Amino-ethoxymethyl)-4-(2-chloro-phenyl)-6-methylsulfanylmethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid diethyl ester
  参考文献：
  名称：

  Long-acting dihydropyridine calcium antagonists. 9. Structure activity relationships around amlodipine

  摘要：

  The preparation of a range of 1,4-dihydropyridine analogues of amlodipine has been undertaken and their calcium antagonist activities on rat aorta have been evaluated. Increasing the size of the C5 ester group dramatically reduces calcium antagonist activity, a trend which would be compatible with the carbonyl group of that ester binding to the DHP receptor. Amlodipine analogues with extended C3 ester substituents also have lower potency than amlodipine, possibly because of disruption of a favourable interaction between the protonated amino group on the 2-substituent and the DHP receptor. Replacement of the 6-methyl substituent in amlodipine by alkoxyalkyl groups or electron-withdrawing groups is also detrimental to calcium antagonist activity.

  DOI：

  10.1016/0223-5234(91)90132-7
• 作为产物：
  描述：

  4-methylthioacetoacetic acid ethyl ester 在 氨 作用下， 以 乙醇 为溶剂， 生成 β-amino-γ-methylthiocrotonic acid ethyl ester
  参考文献：
  名称：

  Long-acting dihydropyridine calcium antagonists. 9. Structure activity relationships around amlodipine

  摘要：

  The preparation of a range of 1,4-dihydropyridine analogues of amlodipine has been undertaken and their calcium antagonist activities on rat aorta have been evaluated. Increasing the size of the C5 ester group dramatically reduces calcium antagonist activity, a trend which would be compatible with the carbonyl group of that ester binding to the DHP receptor. Amlodipine analogues with extended C3 ester substituents also have lower potency than amlodipine, possibly because of disruption of a favourable interaction between the protonated amino group on the 2-substituent and the DHP receptor. Replacement of the 6-methyl substituent in amlodipine by alkoxyalkyl groups or electron-withdrawing groups is also detrimental to calcium antagonist activity.

  DOI：

  10.1016/0223-5234(91)90132-7

文献信息

• 1,4-Dihydropyridine derivatives substituted in the 2 position, and their
  申请人：Bayer Aktiengesellschaft

  公开号：US04188395A1

  公开（公告）日：1980-02-12

  The present invention provides 1,4-dihydropyridine derivatives of the formula in which ##STR1## R represents hydrogen, alkyl, alkenyl, alkoxyalkyl, aryl or aralkyl, the alkyl and aryl groups being optionally substituted, A represents a straight-chain or branched alkylene radical, R.sup.1 represents (a) an optionally substituted alkylthio group or (b) a group of the formula O--CO-alkyl, O--CO-aryl or O--CO-aralkyl, the alkyl and aryl groups being optionally substituted or (c) a phthalimido radical which is optionally substituted in the benzene ring, Y and Z are identical or different and each represents a group of the formula COOR.sup.2 or COR.sup.2, wherein R.sup.2 represents alkyl, alkenyl, alkinyl, alkoxyalkyl, hydroxyalkyl, aminoalkyl, alkylaminoalkyl or aralkyl, the alkyl and aryl radicals being optionally substituted, or Y and Z are identical or different and each represents a cyano radical or a radical of the formula S(O).sub.n --R.sup.3, wherein R.sup.3 represents alkyl, alkenyl, alkoxyalkyl, aminoalkyl, alkylaminoalkyl, aryl or aralkyl, the alkyl and aryl radicals mentioned being optionally substituted, and n represents 0, 1 or 2, R.sup.4 represents hydrogen or alkyl, the alkyl radical being optionally substituted or interrupted by oxygen, or represents the radical A--R.sup.1, wherein A and R.sup.1 have the abovementioned meaning, and X represents an aryl radical, which optionally contains one to three identical or different substituents selected from phenyl, alkyl, alkenyl, alkinyl, alkoxy, alkinoxy, acyloxy, halogen, trifluoromethyl, trifluoromethoxy, hydroxyl, nitro, cyano, azido, amino, alkylamino, acylamino, carbalkoxy, carboxamido, sulphonamide and S(O).sub.n -alkyl (n=0 to 2), or represents a quinolyl, pyridyl, pyrimidyl, thienyl, furyl or pyrryl radical which is optionally substituted by alkyl, alkylamino, nitro or halogen, or represents an optionally substituted aralkyl, cycloalkyl, cycloalkenyl or styryl radical, and acid addition salts thereof. Also included in the invention are methods for the preparation of the 1,4-dihydropyridine derivatives of the invention, compositions containing said derivatives and methods for their use.

  本发明提供了公式中的1,4-二氢吡啶衍生物，其中##STR1## R代表氢、烷基、烯基、烷氧基烷基、芳基或芳基烷基，烷基和芳基基团可选择性地被取代，A代表直链或支链烷基基团，R.sup.1代表(a)可选择性取代的烷基硫基团或(b)公式O--CO-烷基、O--CO-芳基或O--CO-芳基烷基的基团，其中烷基和芳基基团可选择性地被取代，或(c)苯环中可选择性取代的邻苯二甲酰亚胺基团，Y和Z相同或不同，每个代表COOR.sup.2或COR.sup.2的基团，其中R.sup.2代表烷基、烯基、炔基、烷氧基烷基、羟基烷基、氨基烷基、烷基氨基烷基或芳基烷基，所述烷基和芳基基团可选择性被取代，或Y和Z相同或不同，每个代表氰基或公式S(O).sub.n --R.sup.3的基团，其中R.sup.3代表烷基、烯基、烷氧基烷基、氨基烷基、烷基氨基烷基、芳基或芳基烷基，所述所述烷基和芳基基团可选择性被取代，n代表0、1或2，R.sup.4代表氢或烷基，所述烷基基团可选择性被取代或被氧中断，或代表基团A--R.sup.1，其中A和R.sup.1具有上述所述的含义，X代表一个芳基基团，可选择性地含有一个至三个从苯基、烷基、烯基、炔基、烷氧基、烷氧基、酰氧基、卤素、三氟甲基、三氟甲氧基、羟基、硝基、氰基、叠氮基、氨基、烷基氨基、酰胺基、羧酰氧基、羧胺基、磺酰胺基和S(O).sub.n -烷基（n=0至2）中选择的相同或不同取代基，或代表一个可选择性取代的喹啉基、吡啶基、嘧啶基、噻吩基、呋喃基或吡咯基基团，该基团可选择性地被烷基、烷基氨基、硝基或卤素取代，或代表一个可选择性取代的芳基烷基、环烷基、环烯基或芳基烯基基团，以及其酸加盐。该发明还包括了制备所述衍生物的1,4-二氢吡啶的方法、含有所述衍生物的组合物以及其使用方法。
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