1-dodecyl-3-((4,4,6a,6b,8a,11,12,14b-octamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14, 14a,14b-icosahydropicen-3-yloxy)carbonyl)pyridinium bromide | 1443125-11-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 1-dodecyl-3-((4,4,6a,6b,8a,11,12,14b-octamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14, 14a,14b-icosahydropicen-3-yloxy)carbonyl)pyridinium bromide
• 英文别名: [(3S,4aR,6aR,6bS,8aR,11R,12S,12aR,14aR,14bR)-4,4,6a,6b,8a,11,12,14b-octamethyl-2,3,4a,5,6,7,8,9,10,11,12,12a,14,14a-tetradecahydro-1H-picen-3-yl] 1-dodecylpyridin-1-ium-3-carboxylate;bromide
• CAS: 1443125-11-8
• 化学式: Br*C₄₈H₇₈NO₂
• 分子量: 781.057
• InChiKey: NTODETBXCVOUSE-LYWPEHSLSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  10.1
• 重原子数：
  52
• 可旋转键数：
  14
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  α-香树精 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 40.0h， 生成 1-dodecyl-3-((4,4,6a,6b,8a,11,12,14b-octamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14, 14a,14b-icosahydropicen-3-yloxy)carbonyl)pyridinium bromide
  参考文献：
  名称：

  Synthesis of novel triterpene and N-allylated/N-alkylated niacin hybrids as α-glucosidase inhibitors

  摘要：

  Diabetes mellitus is a metabolic disorder characterized by chronic hyperglycemia. alpha-Glucosidase (EC 3.2.1.20) inhibitors interfere with enzymatic action to slow down the liberation of D-glucose from oligosaccharides and disaccharides, resulting in delayed glucose absorption and decreased postprandial plasma glucose levels. In continuation of our drug discovery program on antidiabetic agents, we synthesized novel N-allylated/N-alkylated niacin and alpha-amyrin (4-9) and lupeol (12-16) hybrids and tested for their alpha-glucosidase inhibiting activity. Compounds 4-9 showed better activity profile than the marketed alpha-glucosidase inhibitor i.e. acarbose. Compound 4 possess the highest inhibitory action with IC50 of 5 mu M. Kinetic and CD studies revealed that 4 inhibited the alpha-glucosidase in a noncompetitive manner and caused conformational changes in secondary structure of the enzyme protein. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.01.053

文献信息

• Synthesis of novel triterpene and N-allylated/N-alkylated niacin hybrids as α-glucosidase inhibitors
  作者：Tadigoppula Narender、Gaurav Madhur、Natasha Jaiswal、Manali Agrawal、Chandan K. Maurya、Neha Rahuja、Arvind K. Srivastava、Akhilesh K. Tamrakar

  DOI：10.1016/j.ejmech.2013.01.053

  日期：2013.5

  Diabetes mellitus is a metabolic disorder characterized by chronic hyperglycemia. alpha-Glucosidase (EC 3.2.1.20) inhibitors interfere with enzymatic action to slow down the liberation of D-glucose from oligosaccharides and disaccharides, resulting in delayed glucose absorption and decreased postprandial plasma glucose levels. In continuation of our drug discovery program on antidiabetic agents, we synthesized novel N-allylated/N-alkylated niacin and alpha-amyrin (4-9) and lupeol (12-16) hybrids and tested for their alpha-glucosidase inhibiting activity. Compounds 4-9 showed better activity profile than the marketed alpha-glucosidase inhibitor i.e. acarbose. Compound 4 possess the highest inhibitory action with IC50 of 5 mu M. Kinetic and CD studies revealed that 4 inhibited the alpha-glucosidase in a noncompetitive manner and caused conformational changes in secondary structure of the enzyme protein. (C) 2013 Elsevier Masson SAS. All rights reserved.