Oleoyl-L-valinolamide | 1100978-51-5

• 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: Oleoyl-L-valinolamide
• 英文别名: oleoyl-L-valinol；(9Z)-octadec-9-enoic acid ((S)-1-hydroxymethyl-2-methyl-propyl)-amide；(Z)-N-[(2S)-1-hydroxy-3-methylbutan-2-yl]octadec-9-enamide
• CAS: 1100978-51-5
• 化学式: C₂₃H₄₅NO₂
• 分子量: 367.616
• InChiKey: FCFWNUVBSVWFHR-SSSWZJSRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  26
• 可旋转键数：
  18
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Oleoyl-L-valinolamide 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 VPC 40105
  参考文献：
  名称：

  [EN] NOVEL LYSOPHOSPHATIDIC ACID RECEPTOR SELECTIVE ANTAGONISTS
  [FR] NOUVEAUX ANTAGONISTES SELECTIFS DU RECEPTEUR DE L'ACIDE LYSOPHOSPHATIDIQUE

  摘要：

  公开号：

  WO2005115150A3
• 作为产物：
  描述：

  油酸 在 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 吡啶 为溶剂， 反应 24.0h， 生成 Oleoyl-L-valinolamide
  参考文献：
  名称：

  [EN] COMPOUNDS AND METHODS OF TREATING OBESITY
  [FR] COMPOSÉS ET PROCÉDÉS POUR LE TRAITEMENT DE L'OBÉSITÉ

  摘要：

  公开号：

  WO2009109973A3

文献信息

• 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。
• Compounds and methods of treating obesity
  申请人：Yissum Research Development Company of the Hebrew University of Jerusalem Ltd.

  公开号：US09428448B2

  公开（公告）日：2016-08-30

  Provided are new fatty acid derivatives, methods for their preparation, pharmaceutical compositions including such compounds, and methods of using these compounds and compositions, e.g., as agents for the treatment of obesity and related disorders, and for improving cognition.

  本发明提供了新的脂肪酸衍生物、其制备方法、包括这些化合物的药物组合物，以及使用这些化合物和组合物的方法，例如作为治疗肥胖和相关疾病的药物和改善认知的药物。
• 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.
• FATTY ACID DERIVATIVES FOR USE IN A METHOD OF TREATING DEPRESSION AND ASSOCIATED CONDITIONS
  申请人：YISSUM RESEARCH DEVELOPMENT COMPANY OF THE HEBREW UNIVERSITY OF JERUSALEM LTD.

  公开号：US20150202179A1

  公开（公告）日：2015-07-23

  The invention provides fatty acid derivatives for use in a method of treatment of at least one disease, disorder or condition selected from anxiety, depression, conditions associated menopause, stress, bipolar disorder, neuropathic pain and fibromyalgia.
• US9428448B2
  申请人：——

  公开号：US9428448B2

  公开（公告）日：2016-08-30