(S)-4-trimethylammonio-3-[(tetradecylcarbamoyl)amino]butyrate

• 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: (S)-4-trimethylammonio-3-[(tetradecylcarbamoyl)amino]butyrate
• 英文别名: S-4-trimethylammonium-3-(tetradecylcarbamyl)-aminobutyrate；[3-Carboxy-2-(3-tetradecyl-ureido)-propyl]-trimethyl-ammonium；(3S)-3-(tetradecylcarbamoylamino)-4-(trimethylazaniumyl)butanoate
• 化学式: C₂₂H₄₅N₃O₃
• 分子量: 399.618
• InChiKey: BMZYTDRMCBZVNH-FQEVSTJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  28
• 可旋转键数：
  17
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  81.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  异氰酸十四酯 、 (S)-aminocarnitine 以 二甲基亚砜 为溶剂， 反应 60.0h， 生成 (S)-4-trimethylammonio-3-[(tetradecylcarbamoyl)amino]butyrate
  参考文献：
  名称：

  发现长链氨基甲酰基氨基肉碱衍生物，这是一种具有抗酮症和抗糖尿病活性的可逆肉碱棕榈酰转移酶抑制剂。

  摘要：

  报道了可逆的CPT I抑制剂作为潜在的抗酮药和抗糖尿病药的合成和药理活性。这类抑制剂构成一系列具有通式（CH 3）3 N + CH 2 CH（ZR）CH 2 COO-（Z ＝脲基，氨基甲酸酯基，磺酰胺基和磺酰胺基； R ＝ C 7 -C 14线性烷基链）的对映体纯的氨基肉碱衍生物。基于完整大鼠肝线粒体中CPT I活性评估的主要药理筛选显示，尿素衍生物17（ZR = NHCONHR，R = C14），磺酰胺衍生物7的（R）形式具有最佳活性。 （ZR = NHSO2R，R = C12）和磺酰胺衍生物9（ZR = NHSO2NHR，R = C11）。IC50值分别为1.1、0.7和0.8 microM。对于氨基甲酸酯衍生物11（ZR = NHCOOR，R = C8），观察到的IC50为9.5 microM。此外，对于尿酸化合物17（IC50（M-CPT I）vs IC50（L-CPTI）= 39

  DOI：

  10.1021/jm020979u

文献信息

• PROCESS FOR THE PREPARATION OF (R)- OR (S)-AMINOCARNITINE INNER SALT, THE SALTS AND DERIVATIVES THEREOF
  申请人：SIGMA-TAU Industrie Farmaceutiche Riunite S.p.A.

  公开号：EP1409448B1

  公开（公告）日：2006-11-29
• REGULATION OF FOOD INTAKE AND GLUCOSE PRODUCTION BY MODULATION OF LONG-CHAIN FATTY ACYL-CoA LEVELS IN THE HYPOTHALAMUS
  申请人：ALBERT EINSTEIN COLLEGE OF MEDICINE OF YESHIVA UNIVERSITY

  公开号：EP1594439A2

  公开（公告）日：2005-11-16
• Regulation of food intake and glucose production by modulation of long-chain fatty acyl-coa levels in the hypothalamus
  申请人：Rossetti Luciano

  公开号：US20070093434A1

  公开（公告）日：2007-04-26

  Methods of reducing food intake and glucose production in a mammal, or restoring hepatic autoregulation are provided. The methods involve increasing long-chain fatty acyl-Co-A (LC-CoA) levels in the hypothalamus, or stimulating efferent fibers in the hepatic branch of the vagus nerve. Also provided are methods of increasing food intake and glucose production in a mammal. The methods involve decreasing long-chain fatty acyl-Co-A (LC-CoA) levels in the hypothalamus of the mammal.
• US7705016B2
  申请人：——

  公开号：US7705016B2

  公开（公告）日：2010-04-27
• [EN] REGULATION OF FOOD INTAKE AND GLUCOSE PRODUCTION BY MODULATION OF LONG-CHAIN FATTY ACYL-CoA LEVELS IN THE HYPOTHALAMUS<br/>[FR] REGULATION DE LA PRISE ALIMENTAIRE ET DE LA PRODUCTION DE GLUCOSE PAR MODULATION DES NIVEAUX D'ACYL-COA GRAS DE CHAINE LONGUE DANS L'HYPOTHALAMUS
  申请人：EINSTEIN COLL MED

  公开号：WO2004071458A2

  公开（公告）日：2004-08-26

  Methods of reducing food intake and glucose production in a mammal, or restoring hepatic autoregulation are provided. The methods involve increasing long-chain fatty acyl-Co-A (LC-CoA) levels in the hypothalamus, or stimulating efferent fibers in the hepatic branch of the vagus nerve. Also provided are methods of increasing food intake and glucose production in a mammal. The methods involve decreasing long-chain fatty acyl-Co-A (LC-CoA) levels in the hypothalamus of the mammal.