N-[2-(3,4-二羟基苯基)乙基]十八烷酰胺 | 105955-10-0

• 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]十八烷酰胺
• 英文名称: N-stearoyldopamine
• 英文别名: N-[2-(3,4-dihydroxyphenyl)ethyl]octadecanamide；N-stearoyl dopamine；N-stearoyl-dopamine；T5678727；CAP1241
• CAS: 105955-10-0
• 化学式: C₂₆H₄₅NO₃
• 分子量: 419.648
• InChiKey: KOCSVLPLQCBIGW-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)：
  7.7
• 重原子数：
  30
• 可旋转键数：
  19
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  3

安全信息

• 海关编码：
  2924299090
• 储存条件：
  -20°C

反应信息

• 作为产物：
  描述：

  硬脂酸 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 19.0h， 生成 N-[2-(3,4-二羟基苯基)乙基]十八烷酰胺
  参考文献：
  名称：

  Structure and Thermotropic Phase Behavior of a Homologous Series of BioactiveN-Acyldopamines

  摘要：

  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.

  DOI：

  10.1021/jp402750m

文献信息

• Inhibition of in Vitro Prostaglandin and Leukotriene Biosyntheses by Cinnamoyl-.BETA.-phenethylamine and N-Acyldopamine Derivatives.
  作者：Chen-Fang TSENG、Satoshi IWAKAMI、Akihiro MIKAJIRI、Masaaki SHIBUYA、Fumio HANAOKA、Yutaka EBIZUKA、Kosashi PADMAWINATA、Ushio SANKAWA

  DOI：10.1248/cpb.40.396

  日期：——

  N-trans- and N-cis-Feruloyltyramines were isolated as the inhibitors of in vitro prostaglandin (PG) synthesis from an Indonesian medicinal plant, Ipomoea aquatica (Convolvulaceae). In order to clarify structure activity relationships, cinnamoyl-β-phenethylamines with possible combinations of naturally occurring cinnamic acids and β-phenethylamines were synthesized and tested for their inhibitory activities against PG synthetase and arachidonate 5-lipoxygenase. The compounds containing catechol groups such as N-caffeoyl-β-phenethylamine (CaP) showed higher inhibitory effects on PG synthetase. The catechol group was found to be essential for the inhibition of arachidonate 5-lipoxygenase. The investigation of concentration dependent effects on PG biosynthesis revealed that CaP enhanced PG biosynthesis at a lower concentration range, whereas it inhibited the reaction at a higher concentration. The effects of CaP on each reaction step were investigated with purified PG endoperoxide synthase and microsomal PG synthetase. CaP inhibited the cyclooxygenase reaction, while it enhanced the hydroperoxidase reaction. N-Acyldopamines which contain catechol and lipophylic group were synthesized from dopamine and fatty acids to test their inhibitory effects on arachidonate 5-lipoxygenase. N-Linoleoyldopamine was the most active compound and its IC50 value was 2.3nM in our assay system, in which an IC50 value of AA 861, a specific inhibitor of 5-lipoxygenase, was 8nM.

  N-反式和N-顺式-阿魏酰基酪胺是从印尼药用植物空心菜（旋花科）中分离得到的体外前列腺素（PG）合成抑制剂。为了阐明结构活性关系，合成了可能由天然存在的肉桂酸和β-苯乙胺组合得到的肉桂酰-β-苯乙胺，并测试了它们对PG合成酶和花生四烯酸5-脂氧合酶的抑制活性。含有儿茶酚基团的化合物，如N-咖啡酰基-β-苯乙胺（CaP），显示出对PG合成酶更高的抑制效果。儿茶酚基团被发现对抑制花生四烯酸5-脂氧合酶至关重要。对浓度依赖性PG生物合成效应的研究表明，CaP在较低浓度范围内增强了PG生物合成，而在较高浓度下抑制了反应。通过纯化的PG内过氧化物合成酶和微粒体PG合成酶研究了CaP对每个反应步骤的影响。CaP抑制了环氧合酶反应，同时增强了氢过氧化物酶反应。从多巴胺和脂肪酸合成了含有儿茶酚和脂溶性基团的N-酰基多巴胺，以测试它们对花生四烯酸5-脂氧合酶的抑制效果。N-亚油酰多巴胺是最活跃的化合物，在我们的测定系统中其IC50值为2.3nM，而作为5-脂氧合酶特异性抑制剂的AA 861的IC50值为8nM。
• SUBTANCES FOR THE PROTECTION OF CELLS AND/OR TISSUES
  申请人：Losel Ralf

  公开号：US20100129436A1

  公开（公告）日：2010-05-27

  The invention relates to substances that are suitable for protecting cells and/or tissues.

  这项发明涉及适用于保护细胞和/或组织的物质。
• 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。
• SELF-HEALING CROSS-LINKABLE SHELLS
  申请人：ECOLE POLYTECHNIQUE FEDERALE DE LAUSANNE (EPFL)

  公开号：EP3563871A1

  公开（公告）日：2019-11-06

  The present invention relates to self-healing shells comprising a self-healing shell incorporating amphiphilic molecules having metal-coordinating group(s) reversibly cross-linked with metal cations.

  本发明涉及自愈合外壳，该外壳包含一种自愈合外壳，其中包含有与金属阳离子可逆交联的金属配位基团的两性分子。
• NON-STEROIDAL SELECTIVE GLUCOCORTICOID RECEPTOR AGONISTIC MODULATORS (SEGRAMS) AND USES THEREOF
  申请人：Association pour la recherche à l'IGBMC (ARI)

  公开号：EP3569228A1

  公开（公告）日：2019-11-20

  The present invention relates to the two enantiomers of a SElective Glucocorticoid Receptor Agonistic Modulator (SEGRAM) of Formula 1 or a derivative thereof; to a deuterated form of a SEGRAM of Formula 1 or a derivative thereof; and to the two deuterated enantiomers of a SEGRAM of Formula 1 or a derivative thereof: or a pharmaceutically acceptable salt, solvate and/or prodrug thereof. The present invention also relates to a SEGRAM of Formula 1 or a derivative thereof, or a pharmaceutically acceptable enantiomer, deuterated form, salt, solvate and/or prodrug thereof, for use in the prevention or treatment of an inflammatory disorder in a subject in need thereof.

  本发明涉及式 1 的 SElective Glucocorticoid Receptor Agonistic Modulator（SEGRAM）的两种对映体或其衍生物；涉及式 1 的 SEGRAM 的一种氚代形式或其衍生物；以及涉及式 1 的 SEGRAM 的两种氚代对映体或其衍生物： 或其药学上可接受的盐、溶液剂和/或原药。 本发明还涉及一种式1的SEGRAM或其衍生物，或其药学上可接受的对映体、氘代形式、盐、溶液剂和/或原药，用于预防或治疗有需要的受试者的炎症性疾病。