N-cyclopentyl-palmitoyl amide

• 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: N-cyclopentyl-palmitoyl amide
• 英文别名: Hexadecanoic acid cyclopentylamide；N-cyclopentylhexadecanamide
• 化学式: C₂₁H₄₁NO
• 分子量: 323.563
• InChiKey: AQMKNQJYMDENMS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  23
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  环戊胺 、 棕榈酰氯 以 二氯甲烷 为溶剂， 以73%的产率得到N-cyclopentyl-palmitoyl amide
  参考文献：
  名称：

  Modifications of the Ethanolamine Head in N-Palmitoylethanolamine:  Synthesis and Evaluation of New Agents Interfering with the Metabolism of Anandamide

  摘要：

  The endogenous fatty acid amide anandamide (AEA) has, as a result of its actions on cannabinoid and vanilloid receptors, a number of important pharmacological properties including effects on nociception, memory processes, spasticity, and cell proliferation. Inhibition of the metabolism of AEA, catalyzed by fatty acid amide hydrolase (FAAH), potentiates the actions of AEA in vivo and therefore may be a useful target for drug development. In the present study, we have investigated whether substitution of the headgroup of the endogenous alternative FAAH substrate palmitoylethanolamide (PEA) can result in the identification of novel compounds preventing AEA metabolism. Thirty-seven derivatives of PEA were synthesized, with the C16 long chain of palmitic acid kept intact, and comprising 20 alkylated, 12 aromatic, and 4 halogenated amides. The ability of the PEA derivatives to inhibit FAAH-catalyzed hydrolysis of [H-3]AEA was investigated using rat brain homogenates as a source of FAAH. Inhibition curves were analyzed to determine the potency of the inhibitable fraction (pI(50) values) and the maximal attained inhibition for the compound, given that solubility in an aqueous environment is a major issue for these compounds. In the alkylamide family, palmitoylethyl-amide and palmitoylallylamide were inhibitors of AEA metabolism with PI50 values of 5.45 and 5.47, respectively. Halogenated derivatives (Cl and Br) exhibit PI50 values of similar to5.5 but rather low percentages of maximal inhibition. The -OH group of the ethyl head chain of N-palmitoylethanolamine was not necessary for interaction with FAAH. Amides containing aromatic moieties were less potent inhibitors of AEA metabolism. Compounds containing amide and ester bonds, 13 and 37, showed PI50 values of 4.99 and 5.08, respectively. None of the compounds showed obvious affinity for CB1 or CB2 receptors expressed on Chinese hamster ovary (CHO) cells. It is concluded that although none of the compounds were dramatically more potent than PEA itself at reducing the metabolism of AEA, the lack of effect of the compounds at CB1 and CB2 receptors makes them useful templates for development of possible therapeutic FAAH inhibitors.

  DOI：

  10.1021/jm0209679

文献信息

• New endocannabinoid-like compounds and their use
  申请人：RESEARCH & INNOVATION SOC. COOP. A R.L.

  公开号：EP1900365A2

  公开（公告）日：2008-03-19

  The present invention describes compounds deriving from chemical reactions between saturated or monounsaturated acyl derivatives and primary amines or primary alcohols that display specific cannabinoid-like pharmacological activity without exhibiting the central unwanted side effects typical of synthetic cannabinoids or endocannabinoids acting on central cannabinoid (CB1) receptors. These compounds, having this pharmacological activity, may be utilised to prevent or to treat pathological conditions and diseases in mammals, including human subjects, that may undergo a clinical improvement upon their administration.

  本发明描述了由饱和或单不饱和酰基衍生物与伯胺或伯醇之间的化学反应所产生 的化合物，这些化合物显示出类似大麻素的特殊药理活性，而不会表现出合成大麻 素或作用于中枢大麻素（CB1）受体的内源性大麻素所特有的中枢性不良副作用。这些具有这种药理活性的化合物可用于预防或治疗哺乳动物（包括人类）的病理状况和疾病，服用后可改善临床症状。
• USE OF ENDOCANNABINOID-LIKE COMPOUNDS FOR TREATING CNS DEGENERATIVE DISORDERS
  申请人：Research & Innovation S.p.A.

  公开号：EP1592418B1

  公开（公告）日：2017-09-06
• USE IN THERAPY OF ENDOCANNABINOID-LIKE COMPOUNDS
  申请人：Research & Innovation Soc. Coop. A R.L.

  公开号：EP1592418A2

  公开（公告）日：2005-11-09
• Endocannabinoid-like compounds and their use for treating dermatitis
  申请人：Research & Innovation S.p.A.

  公开号：EP1900365B1

  公开（公告）日：2011-03-30
• [EN] NEW ENDOCANNABINOID-LIKE COMPOUNDS AND THEIR USE<br/>[FR] NOUVEAUX COMPOSES DE TYPE ENDOCANNABINOIDE ET LEUR UTILISATION
  申请人：RES & INNOVATION SOC COOP A R

  公开号：WO2004069240A2

  公开（公告）日：2004-08-19

  The present invention describes compounds deriving from chemical reactions between saturated or monounsaturated acyl derivatives and primary alcohols that display specific cannabinoid-like pharmacological activity without exhibiting the central unwanted side effects typical of synthetic cannabinoids or endocannabinoids acting on central cannabinoid (CB1) receptors. These compounds, having this pharmacological activity, may be utilised to prevent or to treat pathological conditions and diseases in mammals, including human subjects, that may undergo a clinical improvement upon their administration.