N-1-(4-hydroxyphenyl) hexadecanamide | 74058-77-8

• 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-(4-hydroxyphenyl) hexadecanamide
• 英文别名: N-(4-hydroxyphenyl)hexadecanamide；N-(p-hydroxyphenyl)hexadecanamide；N-(4-hydroxyphenyl)palmitamide；palmitic acid-(4-hydroxy-anilide)；Palmitinsaeure-(4-hydroxy-anilid)；4-Palmitoylamino-phenol；4'-Hydroxypalmitanilide
• CAS: 74058-77-8
• 化学式: C₂₂H₃₇NO₂
• 分子量: 347.541
• InChiKey: XIOHVMVLOJUORA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 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-(4-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 [4-(Hexadecanoylamino)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：

  棕榈酸 在 三乙胺 作用下， 以 水 、 乙腈 为溶剂， 反应 24.5h， 生成 N-1-(4-hydroxyphenyl) hexadecanamide
  参考文献：
  名称：

  包含α-氨基酸和脂肪酸的对乙酰氨基酚类似物的抑制肝毒性

  摘要：

  献给EJ科里教授在他的90之际个生日。 抽象的 对乙酰氨基酚是一种流行的解热镇痛药，与非甾体类抗炎药（NSAIDs）相比，抗炎作用弱，副作用发生率低。然而，对乙酰氨基酚由于反应性代谢产物N-乙酰基-对苯醌亚胺（NAPQI）而引起肝毒性。通过在水性MeCN中通过相应的混合碳羧酸酐使用受保护的α-氨基酸和脂肪酸的苯胺衍生物，我们以57-99％的产率获得了对乙酰氨基酚类似物。我们还成功地以76–97％的产率合成了AM404类似物，有望降低肝毒性。 对乙酰氨基酚是一种流行的解热镇痛药，与非甾体类抗炎药（NSAIDs）相比，抗炎作用弱，副作用发生率低。然而，对乙酰氨基酚由于反应性代谢产物N-乙酰基-对苯醌亚胺（NAPQI）而引起肝毒性。通过在水性MeCN中通过相应的混合碳羧酸酐使用受保护的α-氨基酸和脂肪酸的苯胺衍生物，我们以57-99％的产率获得了对乙酰氨基酚类似物。我们还成功地以76–97％的产

  DOI：

  10.1055/s-0037-1611893

文献信息

• Monitored aminolysis of 3-acylthiazolidine-2-thione : A new convenient synthesis of amide
  作者：Yoshimitsu Nagao、Kaoru Seno、Kohji Kawabata、Tadayo Miyasaka、Sachiko Takao、Eiichi Fujita

  DOI：10.1016/s0040-4039(00)71520-6

  日期：1980.1
• Nagao, Yoshimitsu; Seno, Kaoru; Kawabata, Kohji, Chemical and pharmaceutical bulletin, 1984, vol. 32, # 7, p. 2687 - 2699
  作者：Nagao, Yoshimitsu、Seno, Kaoru、Kawabata, Kohji、Miyasaka, Tadao、Takao, Sachiko、Fujita, Eiichi

  DOI：——

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

  DOI：——

  日期：——
• Modifications of the Ethanolamine Head in <i>N</i>-Palmitoylethanolamine:  Synthesis and Evaluation of New Agents Interfering with the Metabolism of Anandamide
  作者：Séverine Vandevoorde、Kent-Olov Jonsson、Christopher J. Fowler、Didier M. Lambert

  DOI：10.1021/jm0209679

  日期：2003.4.1

  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.
• De'Conno, Gazzetta Chimica Italiana, 1917, vol. 47 I, p. 108
  作者：De'Conno

  DOI：——

  日期：——