N-(4-hydroxyphenylethyl)decamide | 21469-31-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N-(4-hydroxyphenylethyl)decamide
• 英文别名: N-Decanoyl-tyramin；N-decanoyltyramine；N-[2-(4-hydroxyphenyl)ethyl]decanamide
• CAS: 21469-31-8
• 化学式: C₁₈H₂₉NO₂
• 分子量: 291.434
• InChiKey: NAWJHHYDDZFUPG-UHFFFAOYSA-N

物化性质

• 沸点：
  492.6±28.0 °C(Predicted)
• 密度：
  0.999±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  21
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.61
• 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：

  对羟基苯乙胺 、 癸酰氯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 以57%的产率得到N-(4-hydroxyphenylethyl)decamide
  参考文献：
  名称：

  YUA001, a Novel Aldose Reductase Inhibitor Isolated from Alkalophilic Corynebacterium sp. YUA25. II. Chemical Modification and Biological Activity.

  摘要：

  研究人员合成了一系列新型 N-取代酪胺（2-对羟基苯乙胺）衍生物（1-11），并评估了它们对猪肾醛糖还原酶（EC 1, 1, 1, 21）的抑制活性。在这些化合物中，N-2-对羟基苯乙基马来酰胺酸（10）的醛糖还原酶抑制活性最强，是 YUA0011 的 22 倍。）

  DOI：

  10.7164/antibiotics.54.827

文献信息

• Antiplasmodial Metabolites Isolated from the Marine Octocoral <i>Muricea austera</i>
  作者：Marcelino Gutiérrez、Todd L. Capson、Héctor M. Guzmán、José González、Eduardo Ortega-Barría、Emilio Quiñoá、Ricardo Riguera

  DOI：10.1021/np060007f

  日期：2006.10.1

  Bioassay-guided fractionation of the MeOH extract from the octocoral Muricea austera collected in the Pacific coast of Panama led to the isolation of eight compounds, including three tyramine derivatives (1-3), two steroidal pregnane glycosides ( 4, 5), and three sesquiterpenoids (6-8). Compounds 2-5 are new natural products, and their structures were determined on the basis of their spectroscopic data (HRMS, 1D and 2D NMR, and CD studies). The antiprotozoal activities of the natural compounds 1-8 as well as those of a series of synthetic glycosides (11-22) and tyramine derivatives (23-35) were evaluated in vitro against a drug-resistant Plasmodium falciparum and intracellular form of Trypanosoma cruzi.
• Mechanistic and Structural Analysis of <i>Drosophila melanogaster</i> Arylalkylamine <i>N</i>-Acetyltransferases
  作者：Daniel R. Dempsey、Kristen A. Jeffries、Jason D. Bond、Anne-Marie Carpenter、Santiago Rodriguez-Ospina、Leonid Breydo、K. Kenneth Caswell、David J. Merkler

  DOI：10.1021/bi5006078

  日期：2014.12.16

  Arylalkylamine N-acetyltransferase (AANAT) catalyzes the penultimate step in the biosynthesis of melatonin and other N-acetylarylalkylamides from the corresponding arylalkylamine and acetyl-CoA. The N-acetylation of arylalkylamines is a critical step in Drosophila melanogaster for the inactivation of the bioactive amines and the sclerotization of the cuticle. Two AANAT variants (AANATA and AANATB) have been identified in D. melanogaster, in which AANATA differs from AANATB by the truncation of 35 amino acids from the N-terminus. We have expressed and purified both D. melanogaster AANAT variants (AANATA and AANATB) in Escherichia coli and used the purified enzymes to demonstrate that this N-terminal truncation does not affect the activity of the enzyme. Subsequent characterization of the kinetic and chemical mechanism of AANATA identified an ordered sequential mechanism, with acetyl-CoA binding first, followed by tyramine. We used a combination of pH-activity profiling and site-directed mutagenesis to study prospective residues believed to function in AANATA catalysis. These data led to an assignment of Glu-47 as the general base in catalysis with an apparent pKa of 7.0. Using the data generated for the kinetic mechanism, structure-function relationships, pH-rate profiles, and site-directed mutagenesis, we propose a chemical mechanism for AANATA.
• Sciortino; Du Ban, Bollettino Chimico Farmaceutico, 1968, vol. 107, # 8, p. 506 - 511
  作者：Sciortino、Du Ban

  DOI：——

  日期：——
• Differential scanning calorimetric studies on the thermotropic phase behavior of dry and hydrated forms of N-acyltyramines
  作者：Stevenson Priscilla、D. Sivaramakrishna、Veerappan Anbazhagan

  DOI：10.1016/j.tca.2014.03.030

  日期：2014.6

  In this paper, a homologous series of N-acyltyramine (NATA) - which is biosynthetic precursor for neuroactive lipids, N-acyldopamine - have been synthesized and their thermotropic phase transitions were characterized by differential scanning calorimetry (DSC). NATA undergoes a major sharp endothermic transition with the melting point of the hydrated samples occurs considerably at lower temperature compared to the dry samples. Thermodynamic parameters, transition enthalpy (Delta H-t) and transition entropy (Delta S-t), associated with the chain-melting phase transitions depends linearly on the number of carbon atoms. The contributions of each methylene unit to the transition enthalpy and entropy and the end contributions arising from the head group and the terminal group was determined and reported. These results are very important to understand the thermodynamics basis of NATA phase properties in other membrane lipids. (C) 2014 Elsevier B.V. All rights reserved.
• US3957905A
  申请人：——

  公开号：US3957905A

  公开（公告）日：1976-05-18