N-1-(2-hydroxyphenyl) hexadecanamide | 224455-05-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-1-(2-hydroxyphenyl) hexadecanamide
• 英文别名: o-hydroxyhexadecanilide；palmitic acid-(2-hydroxy-anilide)；Palmitinsaeure-(2-hydroxy-anilid)；2-Palmitoylamino-phenol；O-Hydroxy-Hexadecanilide；N-(2-hydroxyphenyl)hexadecanamide
• CAS: 224455-05-4
• 化学式: C₂₂H₃₇NO₂
• 分子量: 347.541
• InChiKey: IFBOWHSGMKWESR-UHFFFAOYSA-N

物化性质

• 熔点：
  79-80 °C
• 沸点：
  501.1±33.0 °C(Predicted)
• 密度：
  0.987±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  25
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.68
• 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：

  N-1-(2-hydroxyphenyl) hexadecanamide 在 palladium on activated charcoal 四氮唑 、 氢气 、 双氧水 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 2-(palmitoylamino)phenyl dihydrogen phosphate
  参考文献：
  名称：

  Structure−Activity Relationships of Lysophosphatidic Acid:  Conformationally Restricted Backbone Mimetics

  摘要：

  Lysophosphatidic acid (LPA) has associated with it an intriguing cell biology that is thought to be mediated through its interaction with G-protein coupled receptor(s). In an effort to extend the structure-activity relationships of LPA, we have produced a series of LPA analogues in which the glycerol core in LPA was replaced with conformationally restricted aryl substructures. The aryl substructures encompassed aminophenol, resorcinol, dihydroxy benzophenone, and tocopherol systems. The benzophenone moiety was investigated both as a conformationally restricting substructure for LPA and as a possible photoreactive alkylating agent for the LPA receptor(s). All LPA analogues were evaluated for their potency and efficacy in mobilizing calcium ions from internal stores in MDA MB-231 cells. Ten of the 14 analogues exhibited activity in this assay at doses up to 5 mu M; none of the compounds exhibited nonreceptor-mediated lytic activity at this maximal concentration. The receptor response showed surprising tolerance for manipulation in the backbone region of LPA, although none of the compounds were equipotent to LPA. This tolerance for a variety of structures has given us new leads into the realization of novel agonists and antagonists of the LPA receptor(s).

  DOI：

  10.1021/jm970809v
• 作为产物：
  描述：

  2-氨基苯酚 、 棕榈酰氯 以 四氢呋喃 、 苯 为溶剂， 反应 2.0h， 以62%的产率得到N-1-(2-hydroxyphenyl) hexadecanamide
  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

• Fierz-David; Kuster, Helvetica Chimica Acta, 1939, vol. 22, p. 89
  作者：Fierz-David、Kuster

  DOI：——

  日期：——
• A facile, one-pot synthesis, characterization and antimicrobial activity of o-hydroxy anilide derivatives and 1-substituted-1,3-dicyclohexylurea analogs of long chain carboxylic acids
  作者：Nida N. Farshori、Anis Ahmad、Asad U. Khan、Abdul Rauf

  DOI：10.1016/j.ejmech.2011.01.070

  日期：2011.4

  A series of novel o-hydroxy anilide derivatives and 1-substituted-1,3-dicyclohexylurea analogs of long chain carboxylic acids have been synthesized. The structures of the synthesized compounds were elucidated by IR, H-1 NMR, C-13 NMR and mass spectral data. All the synthesized compounds were tested for their antimicrobial activity by disk diffusion assay with slight modifications against Gram-positive, Gram-negative strains of bacteria as well as fungal strains. After that mini mum inhibitory concentrations (MICs), minimum bactericidal concentrations (MBCs) and minimum fungicidal concentrations (MFCs) of all the synthesized compounds were determined. The investigation of antimicrobial screening data revealed that all the tested compounds showed moderate to good microbial inhibitions. Compounds 3e, 4e, 3f and 4f were found to be the most potent antimicrobial agents. (c) 2011 Elsevier Masson SAS. All rights reserved.
• Auwers; Bergs; Winternitz, Justus Liebigs Annalen der Chemie, 1904, vol. 332, p. 206
  作者：Auwers、Bergs、Winternitz

  DOI：——

  日期：——
• (o-ACYL-p-N-ACYLAMINO-PHENYL)-O-PHOSPHOETHANOLAMINES
  申请人：CLARION PHARMACEUTICALS, INC.

  公开号：EP0929557A2

  公开（公告）日：1999-07-21
• [EN] USE OF ALPHA-BISABOLOL AS STABILISER OF HYDROGEN PEROXIDE
  申请人：WELLA AKTIENGESELLSCHAFT

  公开号：WO1988000464A1

  公开（公告）日：1988-01-28

  (EN) A cosmetic contains hydrogen peroxide and alpha-bisabolol having formula (I), which is used to stabilise the hydrogen peroxide.(FR) Un produit cosmétique contient du peroxyde d'hydrogène et de l'alpha-bisabolol ayant la formule (I), ce dernier étant utilisé pour stabiliser le peroxyde d'hydrogène.