N-[2-(3,4-二羟基苯基)乙基]-十六烷酰胺 | 136181-87-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: N-[2-(3,4-二羟基苯基)乙基]-十六烷酰胺
• 中文别名: 神经生长激素
• 英文名称: N-palmitoyldopamine
• 英文别名: N-[2-(3,4-Dihydroxyphenyl)ethyl]hexadecanamide
• CAS: 136181-87-8
• 化学式: C₂₄H₄₁NO₃
• 分子量: 391.594
• InChiKey: TWJJFOWLTIEYFO-UHFFFAOYSA-N

物化性质

• 溶解度：
  温和加热时可在乙醇中溶解至 5 mM

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  28
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  3

制备方法与用途

N-棕榈酰多巴胺(PALDA)是一种内源性长链线性脂肪酸多巴酰胺，对TRPV1无活性。它对内香草醛类物质N-花生四烯酸基多巴胺(NADA)和阿南达胺表现出“随从”效应。

反应信息

• 作为反应物：
  描述：

  N-[2-(3,4-二羟基苯基)乙基]-十六烷酰胺 在 水 、 potassium carbonate 、 potassium iodide 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 42.0h， 生成 4-[2-(3-Carboxypropoxy)-4-[2-(hexadecanoylamino)ethyl]phenoxy]butanoic acid
  参考文献：
  名称：

  [EN] MEDICAL COMPOUNDS
  [FR] COMPOSÉS MÉDICAUX

  摘要：

  公开号：

  WO2019008537A9
• 作为产物：
  描述：

  N-(3,4-dimethoxy-β-phenylethyl)hexadecanamide 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以75%的产率得到N-[2-(3,4-二羟基苯基)乙基]-十六烷酰胺
  参考文献：
  名称：

  Synthesis, DNA Binding and Antitumor Evaluation of Styelsamine and Cystodytin Analogues

  摘要：

  一系列N-14侧链取代的styelsamine（吡啶并[4,3,2-mn]吖啶）和cystodytin（吡啶并[4,3,2-mn]吖啶-4-酮）生物碱类似物已被制备并评估其结合DNA亲和力和对人类肿瘤细胞系的抗增殖活性。总体发现styelsamine类似物是更强的DNA结合剂，天然产物styelsamine B和D具有特别高的亲和力（Kapp分别为5.33 × 10^6 M^-1和3.64 × 10^6 M^-1）。相比之下，cystodytin亚胺醌生物碱对DNA的亲和力较低，但在抑制体外肿瘤细胞增殖方面通常与styelsamine类似物一样活跃。对于多个类似物，观察到对非小细胞肺癌、黑色素瘤和肾癌细胞系的亚组选择性。观察到整个细胞活性和clogP之间的相关性，最强烈的抗增殖活性在3-苯基丙酰胺类似物37和41中观察到（NCI面板平均GI50分别为0.4 μM和0.32 μM），clogP约为4.0-4.5。

  DOI：

  10.3390/md11020274

文献信息

• N-docosahexaenoyl, 3 hydroxytyramine : A dopaminergic compound that penetrates the blood-brain barrier and suppresses appetite
  作者：Victor E. Shashoua、Gary W. Hesse

  DOI：10.1016/0024-3205(96)00101-4

  日期：1996.3

  unsaturation (0-6 double bonds) were used to synthesize dopaminergic compounds for a study of the carrier mediated transport of dopamine (DA) to the brain. The most active carrier was the all cis C22:6 fatty acid [docosahexaenoic acid, (DHA)]which increased DA uptake through the blood-brain barrier by greater than 7.5 fold. The DHA-DA compound, NMI 8739, depressed the general locomotor activity of mice

  具有可变链长（2-22个碳原子长）和不饱和度（0-6个双键）的脂肪酸用于合成多巴胺能化合物，以研究载体介导的多巴胺（DA）向大脑的转运。活性最高的载体是全顺式C22：6脂肪酸[二十二碳六烯酸（DHA）]，它通过血脑屏障的DA摄取增加了7.5倍以上。DHA-DA化合物NMI 8739以剂量依赖性方式抑制了小鼠的总体运动活性。它还以10 mg / kg的剂量分别抑制Balb c小鼠和Charles River大鼠的食欲50％和95％。连续三周每日服用NMI-8739不会引起耐受性。这些结果证明了DHA在载体介导的小分子向大脑转运方面的潜力。
• Efficient <i>N</i>-Acyldopamine Synthesis
  作者：Yotaro Matsumoto、Akihiro Ito、Motonari Uesugi、Atsushi Kittaka

  DOI：10.1248/cpb.c16-00162

  日期：——

  N-Acyldopamines are endogenous analogs of capsaicin that exhibit cannabinoid-like activities and were identified from brain extracts. Among them, N-arachidonoyldopamine (AADA) and N-oleoyldopamine (ODA) were characterized as transient receptor potential vanilloid type V1 channel (TRPV1) ligands. Recently, it was shown that N-acyldopamines may possess diverse physiological roles in addition to their ligand activities. To study the multiple functions and action mechanisms of endogenous N-acyldopamines, a simple and efficient method of N-acyldopamine synthesis was investigated. The eighteen potentially endogenous N-acyldopamines and two deuterated ones, N-palmitoyl dopamine-d5 and N-stearoyl dopamine-d5, were efficiently synthesized without protective groups in CH2Cl2 under optimized conditions using propylphosphoric acid cyclic anhydride (PPACA) as a condensation agent.

  N-Acyldopamines 是辣椒素的内源性类似物，具有类似大麻素的活性，是从脑提取物中鉴定出来的。其中，N-丙烯酰多巴胺（AADA）和 N-油酰多巴胺（ODA）被鉴定为瞬时受体电位香草素 V1 型通道（TRPV1）配体。最近的研究表明，N-乙酰多巴胺除了配体活性外，还可能具有多种生理作用。为了研究内源性 N-acyldopamines 的多种功能和作用机制，我们研究了一种简单高效的 N-acyldopamine 合成方法。在优化的条件下，以丙基磷酸环酐（PPACA）为缩合剂，在CH2Cl2中高效合成了18种潜在的内源性N-acyldopamine和两种氚化的N-棕榈酰多巴胺-d5和N-硬脂酰多巴胺-d5。
• Newly synthesized dopamine ester derivatives and assessment of their antioxidant, antimicrobial and hemolytic activities
  作者：Mohamed Sellami、Ali Châari、Imen Aissa、Mohamed Bouaziz、Youssef Gargouri、Nabil Miled

  DOI：10.1016/j.procbio.2013.07.022

  日期：2013.10

  evaluated for their antioxidant activity using the DPPH and the ABTS tests. Results showed that esterification had little effect on radical-scavenging capacity. However, long chain fatty acid esters displayed higher protective effect of oil against oxidation at 70 °C as compared to the parent dopamine or to the BHT. The hemolytic activity of dopamine esters was studied. Middle chain length derivatives (DA-C

  摘要 多巴胺衍生物的制备是为了应对食品、化妆品和制药行业对新型亲脂抗氧化剂日益增长的需求。使用来自南极念珠菌 (Novozyme 435) 的脂肪酶作为生物催化剂合成了大量具有增加亲脂性的多巴胺酯（DA-C 3 至 DA-C 18:1）。当辛酸（DA-C 8 ）用作酰基供体时，转化率最高（52.75%）。使用 DPPH 和 ABTS 测试纯化合成的化合物并评估其抗氧化活性。结果表明，酯化对自由基清除能力影响不大。然而，与母体多巴胺或 BHT 相比，长链脂肪酸酯在 70°C 下显示出更高的油抗氧化保护作用。研究了多巴胺酯的溶血活性。多巴胺和油酸衍生物（DA-C 18:1）的中链长度衍生物（DA-C 8 和DA-C 12 ）对人红细胞显示出最高的溶血活性。还使用井扩散和最小抑制浓度方法评估了多巴胺酯的抗菌活性。在所有测试化合物中，DA-C 8 和DA-C 12 表现出最高的抗菌活性。这些结果通
• PHARMACEUTICAL AGENT FOR PREVENTION AND TREATMENT OF SKIN DISEASE INDUCED BY ACCELERATED KERATINIZATION
  申请人：Kyoto University

  公开号：EP2127673A1

  公开（公告）日：2009-12-02

  A medicament for prophylactic and/or therapeutic treatment of a dermatosis resulting from excessively advanced keratinization, such as non-hereditary inflammatory keratosis and hereditary congenital keratosis, which comprises a substance selected from the group consisting of a cannabinoid agonist and a vanilloid agonist as an active ingredient.

  一种用于预防和/或治疗过度角化引起的皮肤病（如非遗传性炎症性角化病和遗传性先天性角化病）的药物，其活性成分包括一种从大麻素激动剂和香草素激动剂组成的组中选出的物质。
• Structure and Thermotropic Phase Behavior of a Homologous Series of Bioactive<i>N</i>-Acyldopamines
  作者：S. Thirupathi Reddy、Pradip K. Tarafdar、Ravi Kanth Kamlekar、Musti J. Swamy

  DOI：10.1021/jp402750m

  日期：2013.7.25

  N-Acyldopamines (NADAs), which are present in mammalian nervous tissues, exhibit interesting biological and pharmacological properties. In the present study, a homologous series of NADAs with varying acyl chains (n = 12-20) have been synthesized and characterized. Differential scanning calorimetric studies show that in the dry state the transition temperatures, enthalpies, and entropies of NADAs exhibit odd-even alternation with the values corresponding to the even chain length series being slightly higher. Both even and odd chain length NADAs display a linear dependence of the transition enthalpies and entropies on the chain length. However, odd-even alternation was not observed in the calorimetric properties upon hydration, although the transition enthalpies and entropies exhibit linear dependence. Linear least-squares analyses yielded incremental values contributed by each methylene group to the transition enthalpy and entropy and the corresponding end contributions. N-Lauroyldopamine (NLDA) crystallized in the monoclinic space group C2/c with eight symmetry-related molecules in the unit cell. Single-crystal X-ray diffraction studies show that NLDA molecules are organized in the bilayer form, with a head-to-head (and tail-to-tail) arrangement of the molecules. Water-mediated hydrogen bonds between the hydroxyl groups of the dopamine moieties of opposing layers and N-H center dot center dot center dot O hydrogen bonds between the amide groups of adjacent molecules in the same layer stabilize the crystal packing. These results provide a thermodynamic and structural basis for investigating the interaction of NADAs with other membrane lipids, which are expected to provide clues to understand how they function in vivo, e.g., as signaling molecules in the modulation of pain.