1-(ethoxycarbonyl)-1,2,5,6-tetrahydropyridine-3-carboxylic acid | 189286-20-2

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: 1-(ethoxycarbonyl)-1,2,5,6-tetrahydropyridine-3-carboxylic acid
• 英文别名: 5,6-Dihydro-2h-pyridine-1,3-dicarboxylic acid 1-ethyl ester；1-ethoxycarbonyl-3,6-dihydro-2H-pyridine-5-carboxylic acid
• CAS: 189286-20-2
• 化学式: C₉H₁₃NO₄
• 分子量: 199.207
• InChiKey: GURKPJKUMLVUIQ-UHFFFAOYSA-N

物化性质

• 沸点：
  348.8±42.0 °C(Predicted)
• 密度：
  1.283±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(ethoxycarbonyl)-1,2,5,6-tetrahydropyridine-3-carboxylic acid 在 吡啶 、 盐酸 、 氯化亚砜 作用下， 以 四氢呋喃 、 乙醚 、 氯仿 为溶剂， 反应 9.67h， 生成 5-((E)-1-Methyl-propenyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid ethyl ester
  参考文献：
  名称：

  5-(Alk-1-enyl)-1,2,3,6-tetrahydropyridines as congeners of streptazolin

  摘要：

  描述了与抗生素和抗真菌活性独特天然化合物链霉唑（streptazolin）结构相关的1,3-二烯的合成。模仿两个建议的药效团单元导致了具有增强化学稳定性的化合物，但抗生素活性并没有令人满意的提升。

  DOI：

  10.1039/a607309c
• 作为产物：
  描述：

  氢溴酸槟榔碱 在 水 、 sodium carbonate 、 sodium hydroxide 作用下， 以 水 、 甲苯 为溶剂， 反应 9.25h， 生成 1-(ethoxycarbonyl)-1,2,5,6-tetrahydropyridine-3-carboxylic acid
  参考文献：
  名称：

  N-Heteroarylmethyl-5-hydroxy-1,2,5,6-tetrahydropyridine-3-carboxylic acid a novel scaffold for the design of uncompetitive α-glucosidase inhibitors

  摘要：

  The enzyme alpha-glucosidase has attracted interest owing to its involvement in the digestive process of carbohydrate, its role in intracellular glycoprotein trafficking, tumorigenesis and viral infection. In this study, several members of a new family of N-heteroarylmethyl substituted azasugars were synthesized and evaluated as alpha-glucosidase inhibitors. We systematically investigated the effect of different N-substituents as well as the role of hydroxyl and carboxylate moieties on the piperidine ring. The compounds N-heteroarylmethyl-5-hydroxy-1,2,5,6-tetrahydropyridine-3-carboxylic acid emerged as potent alpha-glucosidase inhibitors. Unlike Acarbose and other clinically relevant alpha-glucosidase inhibitors, these compounds act through a reversible uncompetitive mechanism of inhibition which make them attractive candidates for drug development. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.07.012

文献信息

• Tetrahydro-nicotinsäure und Hexahydro-nicotinsäure als Wachstumsfaktoren bei Staphylococcus aureus und Bacillus Proteus vulgaris
  作者：H. v. Euler、B. Högberg、P. Karrer、H. Salomon、H. Ruckstuhl

  DOI：10.1002/hlca.19440270146

  日期：——
• N-Heteroarylmethyl-5-hydroxy-1,2,5,6-tetrahydropyridine-3-carboxylic acid a novel scaffold for the design of uncompetitive α-glucosidase inhibitors
  作者：Sha Long、Francesca Romana Stefani、Stefano Biondi、Giancarlo Ghiselli、Mauro Panunzio

  DOI：10.1016/j.bmc.2013.07.012

  日期：2013.9

  The enzyme alpha-glucosidase has attracted interest owing to its involvement in the digestive process of carbohydrate, its role in intracellular glycoprotein trafficking, tumorigenesis and viral infection. In this study, several members of a new family of N-heteroarylmethyl substituted azasugars were synthesized and evaluated as alpha-glucosidase inhibitors. We systematically investigated the effect of different N-substituents as well as the role of hydroxyl and carboxylate moieties on the piperidine ring. The compounds N-heteroarylmethyl-5-hydroxy-1,2,5,6-tetrahydropyridine-3-carboxylic acid emerged as potent alpha-glucosidase inhibitors. Unlike Acarbose and other clinically relevant alpha-glucosidase inhibitors, these compounds act through a reversible uncompetitive mechanism of inhibition which make them attractive candidates for drug development. (C) 2013 Elsevier Ltd. All rights reserved.
• 5-(Alk-1-enyl)-1,2,3,6-tetrahydropyridines as congeners of streptazolin
  作者：Martin Kratzel、Alexander Weigl

  DOI：10.1039/a607309c

  日期：——

  The synthesis of 1,3-dienes which are structurally related to streptazolin, a unique natural compound with antibiotic and antifungal activities, is described. Mimicking of two suggested pharmacophoric units leads to compounds with enhanced chemical stability but without any satisfactory gain in antibiotic activity.

  描述了与抗生素和抗真菌活性独特天然化合物链霉唑（streptazolin）结构相关的1,3-二烯的合成。模仿两个建议的药效团单元导致了具有增强化学稳定性的化合物，但抗生素活性并没有令人满意的提升。