methyl 1-benzyl-5-hydroxy-1,2,5,6-tetrahydropyridine-3-carboxylate | 1452109-40-8

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: methyl 1-benzyl-5-hydroxy-1,2,5,6-tetrahydropyridine-3-carboxylate
• 英文别名: Methyl 1-benzyl-5-hydroxy-1,2,5,6-tetrahydropyridine-3-carboxylate；methyl 1-benzyl-3-hydroxy-3,6-dihydro-2H-pyridine-5-carboxylate
• CAS: 1452109-40-8
• 化学式: C₁₄H₁₇NO₃
• 分子量: 247.294
• InChiKey: OXDTUIMTHYQYDV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 1-benzyl-5-hydroxy-1,2,5,6-tetrahydropyridine-3-carboxylate 在 盐酸 作用下， 以 水 为溶剂， 反应 4.5h， 以91%的产率得到1-benzyl-5-hydroxy-1,2,5,6-tetrahydropyridine-3-carboxylic acid hydrochloride
  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
• 作为产物：
  描述：

  3-tert-butyl 5-methyl 7-oxa-3-azabicyclo[4.1.0]heptane-3,5-dicarboxylate 在 N,N-二异丙基乙胺 、 三氟乙酸 、 potassium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 3.83h， 生成 methyl 1-benzyl-5-hydroxy-1,2,5,6-tetrahydropyridine-3-carboxylate
  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

• 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.