N-octanoyl tyramine | 21469-33-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N-octanoyl tyramine
• 英文别名: N-[2-(4-hydroxyphenyl)ethyl]octanamide
• CAS: 21469-33-0
• 化学式: C₁₆H₂₅NO₂
• 分子量: 263.38
• InChiKey: HEHKXKVQGJXAFE-UHFFFAOYSA-N

物化性质

• 沸点：
  472.0±28.0 °C(Predicted)
• 密度：
  1.018±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 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：

  辛酸 在 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 N-octanoyl tyramine
  参考文献：
  名称：

  Analyses of Synthetic N-Acyl Dopamine Derivatives Revealing Different Structural Requirements for Their Anti-inflammatory and Transient-Receptor-Potential-Channel-of-the-Vanilloid-Receptor-Subfamily-Subtype-1 (TRPV1)-Activating Properties

  摘要：

  We studied the chemical entities within N-octanoyl dopamine (NOD) responsible for the activation of transient-receptor-potential channels of the vanilloid-receptor subtype 1 (TRPV1) and inhibition of inflammation. The potency of NOD in activating TRPV1 was significantly higher compared with those of variants in which the ortho-dihydroxy groups were acetylated, one of the hydroxy groups was omitted (N-octanoyl tyramine), or the ester functionality consisted of a bulky fatty acid (N-pivaloyl dopamine). Shortening of the amide linker (Delta NOD) slightly increased its potency, which was further increased when the carbonyl and amide groups (Delta NODR) were interchanged. With the exception of Delta NOD, the presence of an intact catechol structure was obligatory for the inhibition of VCAM-1 and the induction of HO-1 expression. Because TRPV1 activation and the inhibition of inflammation by N-acyl dopamines require different structural entities, our findings provide a framework for the rational design of TRPV1 agonists with improved anti-inflammatory properties.

  DOI：

  10.1021/acs.jmedchem.8b00156

文献信息

• YUA001, a Novel Aldose Reductase Inhibitor Isolated from Alkalophilic Corynebacterium sp. YUA25. II. Chemical Modification and Biological Activity.
  作者：WON-SUCK SUN、HYO-SUNG LEE、JUNG-MIN PARK、SUNG-HAN KIM、JU-HYUN YU、JUNG-HAN KIM

  DOI：10.7164/antibiotics.54.827

  日期：——

  A series of novel N-substituted tyramine (2-p-hydroxyphenylethylamine) derivatives (1-11) were synthesized and evaluated for their inhibitory activity against pig kidney aldose reductase (EC 1, 1, 1, 21). Of these compounds, N-2-p-hydroxyphenylethyl maleamic acid (10) exhibits the strongest aldose reductase inhibitory activity, which is 22 times more potent than that of YUA0011).

  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。）
• [EN] LIPOPHILIC DOPAMINE DERIVATIVES AND THEIR USE<br/>[FR] DÉRIVÉS DE DOPAMINE LIPOPHILES ET LEUR UTILISATION
  申请人：NOVALIQ GMBH

  公开号：WO2013034457A1

  公开（公告）日：2013-03-14

  The invention provides novel lipophilic dopamine derivatives with improved stability and physiological half-life. The compounds may be used for organ and tissue preservation during storage and transport, or in the pre-treatment of organ and tissue donor or recipients. Moreover, they may be used as therapeutic agents for the prevention or treatment of ischaemia-related pathological conditions.

  本发明提供了一种新型的亲脂性多巴胺衍生物，具有改善稳定性和生理半衰期的特点。这些化合物可用于在储存和运输期间进行器官和组织保护，或用于器官和组织供体或受体的预处理。此外，它们可以用作治疗剂，用于预防或治疗缺血相关的病理状况。
• LIPOPHILIC DOPAMINE DERIVATIVES AND THEIR USE
  申请人：NOVALIQ GMBH

  公开号：US20140221485A1

  公开（公告）日：2014-08-07

  The invention provides novel lipophilic dopamine derivatives with improved stability and physiological half-life. The compounds may be used for organ and tissue preservation during storage and transport, or in the pre-treatment of organ and tissue donor or recipients. Moreover, they may be used as therapeutic agents for the prevention or treatment of ischaemia-related pathological conditions.

  本发明提供了一种新型的亲脂性多巴胺衍生物，其稳定性和生理半衰期得到了改善。这些化合物可用于在储存和运输期间进行器官和组织保护，或在器官和组织供体或受体的预处理中使用。此外，它们可以用作治疗药物，用于预防或治疗缺血相关的病理状况。
• 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：——