Palmitoyl-L-valinolamide | 107560-76-9

• 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: Palmitoyl-L-valinolamide
• 英文别名: N-[(2S)-1-hydroxy-3-methylbutan-2-yl]hexadecanamide
• CAS: 107560-76-9
• 化学式: C₂₁H₄₃NO₂
• 分子量: 341.578
• InChiKey: CUAZSQYMXJAXLC-HXUWFJFHSA-N

物化性质

• 沸点：
  489.5±28.0 °C(predicted)
• 密度：
  0.900±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  24
• 可旋转键数：
  17
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  L-缬氨醇 、 棕榈酸 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以87%的产率得到Palmitoyl-L-valinolamide
  参考文献：
  名称：

  Novel Acylethanolamide Derivatives That Modulate Body Weight through Enhancement of Hypothalamic Pro-Opiomelanocortin (POMC) and/or Decreased Neuropeptide Y (NPY)

  摘要：

  Newly synthesized acylethanolamide derivatives oleoyl-L-valinolamide (1), oleoyl-D-valinolamide (2), elaidoyl-L-valinolamide (3), elaidoyl-D-valinolamide (4) stearoyl-L-valinolamide (5), and palmitoyl-L-valinolamide (6) were investigated in mice as antiobesity compounds. Compounds 1, 2, 5, 6 significantly decreased body weight by 6.57% following eight injections of 1 mg/kg ip during 39 days, while 3 and 4 showed no such activity. Receptor binding indicated that no compound activated CB1, CB2, PPAR alpha, or TRPV1 receptors. Hypothalamic RT-PCR showed that mRNA expression of the anorexigenic genes POMC and CART was up-regulated by 1, 2, 5 and 1, 2, respectively, while that of the orexigenic genes NPY and CaMKK2 was down-regulated by the respective compounds 1, 5, 6 and 1, 2, 5. Oleoyl-L-valinolamide enhances anorectic pathways and lead to decreased glucose levels, enhanced locomotor activity, and improved cognition. Effects of oleoyl-L-valinolamide on weight were dose-dependent, and it could be given orally. 1, 2, 4, 5 down-regulated FAAH mRNA expression.

  DOI：

  10.1021/jm300484d

文献信息

• A new determination of the absolute configuration of the chiral amine
  作者：Yoshimitsu Nagao、Masahiro Yagi、Takao Ikeda、Eiichi Fujita

  DOI：10.1016/s0040-4039(00)86786-6

  日期：1982.1

  A new method for assignment of the absolute configuration of the asymmetric carbon atom attached to an amino or imino group using rac.-3-hexadecanoyl-4-methoxycarbonyl-1,3-thiazolidine-2-thione (rac.-HDMTT) (4) is described.

  一种使用rac分配与氨基或亚氨基连接的不对称碳原子的绝对构型的新方法。-3-十六烷酰基-4-甲氧羰基-1,3-噻唑烷-2-硫酮（外消旋。-HDMTT）（4）进行说明。
• COMPOUNDS AND METHODS OF TREATING OBESITY
  申请人：Katzhendler Jehoshua

  公开号：US20110178151A1

  公开（公告）日：2011-07-21

  The present invention relates to novel fatty acid derivatives, methods for their preparation, pharmaceutical compositions including such compounds, and methods of using these compounds and compositions, especially as agents for the treatment of obesity and related disorders, and for improving cognition.

  本发明涉及一种新型脂肪酸衍生物、其制备方法、包括这些化合物的制药组合物，以及使用这些化合物和组合物的方法，特别是作为治疗肥胖和相关疾病的药物和改善认知能力的药物。
• US9428448B2
  申请人：——

  公开号：US9428448B2

  公开（公告）日：2016-08-30
• [EN] COMPOUNDS AND METHODS OF TREATING OBESITY<br/>[FR] COMPOSÉS ET PROCÉDÉS POUR LE TRAITEMENT DE L'OBÉSITÉ
  申请人：YISSUM RES DEV CO

  公开号：WO2009109973A2

  公开（公告）日：2009-09-11

  The present invention relates to novel fatty acid derivatives, methods for their preparation, pharmaceutical compositions including such compounds, and methods of using these compounds and compositions, especially as agents for the treatment of obesity and related disorders, and for improving cognition.
• Novel Acylethanolamide Derivatives That Modulate Body Weight through Enhancement of Hypothalamic Pro-Opiomelanocortin (POMC) and/or Decreased Neuropeptide Y (NPY)
  作者：Yosefa Avraham、Jehoshua Katzhendler、Lia Vorobeiv、Shira Merchavia、Chana Listman、Eithan Kunkes、Fida’ Harfoush、Sawsan Salameh、Aviva F. Ezra、Nikolaos C. Grigoriadis、Elliot M. Berry、Yousef Najajreh

  DOI：10.1021/jm300484d

  日期：2013.3.14

  Newly synthesized acylethanolamide derivatives oleoyl-L-valinolamide (1), oleoyl-D-valinolamide (2), elaidoyl-L-valinolamide (3), elaidoyl-D-valinolamide (4) stearoyl-L-valinolamide (5), and palmitoyl-L-valinolamide (6) were investigated in mice as antiobesity compounds. Compounds 1, 2, 5, 6 significantly decreased body weight by 6.57% following eight injections of 1 mg/kg ip during 39 days, while 3 and 4 showed no such activity. Receptor binding indicated that no compound activated CB1, CB2, PPAR alpha, or TRPV1 receptors. Hypothalamic RT-PCR showed that mRNA expression of the anorexigenic genes POMC and CART was up-regulated by 1, 2, 5 and 1, 2, respectively, while that of the orexigenic genes NPY and CaMKK2 was down-regulated by the respective compounds 1, 5, 6 and 1, 2, 5. Oleoyl-L-valinolamide enhances anorectic pathways and lead to decreased glucose levels, enhanced locomotor activity, and improved cognition. Effects of oleoyl-L-valinolamide on weight were dose-dependent, and it could be given orally. 1, 2, 4, 5 down-regulated FAAH mRNA expression.