N-pentadecanoyl dopamine | 1447947-45-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N-pentadecanoyl dopamine
• 英文别名: NA-Dopamine 15:0；N-[2-(3,4-dihydroxyphenyl)ethyl]pentadecanamide
• CAS: 1447947-45-6
• 化学式: C₂₃H₃₉NO₃
• 分子量: 377.568
• InChiKey: FEPACOWHUYBVKM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.85
• 重原子数：
  27.0
• 可旋转键数：
  16.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  69.56
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  十五烷酸 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-pentadecanoyl dopamine
  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

• 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。
• 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.