3-amino-3-(ethylthio)-2-propenoic acid ethyl ester | 53371-88-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 乙烯基硫酯
• 英文名称: 3-amino-3-(ethylthio)-2-propenoic acid ethyl ester
• 英文别名: Ethyl 3-amino-3-(ethylsulfanyl)prop-2-enoate；ethyl 3-amino-3-ethylsulfanylprop-2-enoate
• CAS: 53371-88-3
• 化学式: C₇H₁₃NO₂S
• 分子量: 175.252
• InChiKey: ARSQIBBOIIGNAO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 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：

  4-吡啶甲醛 、 3-amino-3-(ethylthio)-2-propenoic acid ethyl ester 以 乙醇 为溶剂， 反应 5.0h， 以2-amino-4-(4-pyridyl)-6-ethylmercapto-4,5-dihydropyridine-3,5-dicarboxylic acid diethyl ester of melting point 156° C is obtained的产率得到6-amino-2-ethylsulfanyl-3,4-dihydro-[4,4']bipyridinyl-3,5-dicarboxylic acid diethyl ester
  参考文献：
  名称：

  2-Amino-4,5-dihydropyridine derivatives and process for their preparation

  摘要：

  6-位被低烷氧基或低烷硫基取代的2-氨基-4,5-二氢吡啶-3,5-二羧酸酯化合物，在4-位可被低烷基、苯基、取代苯基或杂环基取代，具有降压剂和冠状血管扩张剂的作用。这些化合物，其中2-氨基-4-(3-硝基苯基)-6-乙氧基-4,5-二氢吡啶-3,5-二羧酸二乙酯是代表性的实施例，通过醛和在3-位带有烷氧基或烷硫基的3-氨基丙烯酸酯的缩合制备。

  公开号：

  US03985886A1

文献信息

• 2-Amino-4,5-dihydropyridine derivatives in pharmaceutical compositions
  申请人：Bayer Aktiengesellschaft

  公开号：US03992545A1

  公开（公告）日：1976-11-16

  2-Amino-4,5-dihydropyridines-3,5-dicarboxylates substituted by lower alkoxy or lower alkylthio in the 6-position and optionally substituted in the 4-position by lower alkyl, phenyl, substituted phenyl or a heterocyclic group are antihypertensive agents and coronary vessel dilators. The compounds, of which 2-amino-4-(3-nitrophenyl)-6-ethoxy-4,5-dihydropyridine-3,5-dicarboxylic acid diethyl ester is a representative embodiment, are prepared through condensation of an aldehyde and a 3-aminoacrylate bearing an alkoxy or alkylthio group in the 3-position.

  在6位被低烷氧基或低烷基硫代基取代的2-氨基-4,5-二氢吡啶-3,5-二羧酸酯中，4位可选择性地被低烷基，苯基，取代苯基或杂环基所取代，这些化合物是降压剂和冠状血管扩张剂。这些化合物通过醛和3-氨基丙烯酸酯在3位带有烷氧基或烷基硫代基的缩合反应制备而成，其中2-氨基-4-(3-硝基苯基)-6-乙氧基-4,5-二氢吡啶-3,5-二羧酸二乙酯是代表性的实施例。
• Dihydropyrimidine calcium channel blockers: 2-heterosubstituted 4-aryl-1,4-dihydro-6-methyl-5-pyrimidinecarboxylic acid esters as potent mimics of dihydropyridines
  作者：Karnail S. Atwal、George C. Rovnyak、Joseph Schwartz、Suzanne Moreland、Anders Hedberg、Jack Z. Gougoutas、Mary F. Malley、David M. Floyd

  DOI：10.1021/jm00167a035

  日期：1990.5

  2-Heterosubstituted-4-aryl-1,4-dihydro-6-methyl-5-pyrimidinecar box ylic acid esters 8, which lack the potential CS symmetry of dihydropyridine calcium channel blockers, were prepared and evaluated for biological activity. Biological assays using potassium-depolarized rabbit aorta and radioligand binding techniques showed that some of these compounds are potent mimics of dihydropyridine calcium channel blockers. The combination of a branched ester (e.g. isopropyl, sec-butyl) and an alkylthio group (e.g. SMe) was found to be optimal for biological activity. When compared directly with similarly substituted 2-heteroalkyldihydropyridines 9, dihydropyrimidines 8 were found to be 30-fold less active. The solid-state structure of dihydropyrimidine analogue 8g shows that these compounds can adopt a molecular conformation which is similar to the reported conformation of dihydropyridine calcium channel blockers.