(4Z,7Z,10Z,13Z,16Z,19Z)-N-(3-hydroxypropyl)docosa-4,7,10,13,16,19-hexaenamide | 1404478-51-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (4Z,7Z,10Z,13Z,16Z,19Z)-N-(3-hydroxypropyl)docosa-4,7,10,13,16,19-hexaenamide
• CAS: 1404478-51-8
• 化学式: C₂₅H₃₉NO₂
• 分子量: 385.59
• InChiKey: CEUUMIWQKVFXSA-KUBAVDMBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  28
• 可旋转键数：
  17
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4Z,7Z,10Z,13Z,16Z,19Z)-N-(3-hydroxypropyl)docosa-4,7,10,13,16,19-hexaenamide 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 3-[[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyl]amino]propyl N-[amino-[[amino(dimethylamino)methylidene]amino]methylidene]carbamate
  参考文献：
  名称：

  FATTY ACID GUANIDINE AND SALICYLATE GUANIDINE DERIVATIVES AND THEIR USES

  摘要：

  这项发明涉及脂肪酸胍或水杨酸胍衍生物；包含有效量脂肪酸胍或水杨酸胍衍生物的组合物；以及治疗或预防代谢性疾病的方法，包括给予有效量脂肪酸胍或水杨酸胍衍生物。

  公开号：

  US20120277305A1
• 作为产物：
  描述：

  (4Z,7Z,10Z,13Z,16Z,19Z)-4,7,10,13,16,19-二十二碳六烯酸乙酯 、 3-氨基-1-丙醇 以 neat (no solvent) 为溶剂， 反应 24.0h， 以69%的产率得到(4Z,7Z,10Z,13Z,16Z,19Z)-N-(3-hydroxypropyl)docosa-4,7,10,13,16,19-hexaenamide
  参考文献：
  名称：

  Synthesis and discovery of ω-3 polyunsaturated fatty acid- alkanolamine (PUFA-AA) derivatives as anti-inflammatory agents targeting Nur77

  摘要：

  In this work, three series of ω-3 polyunsaturated fatty acid-alkanolamine derivatives (PUFA-AAs) were synthesized, characterized and their anti-inflammatory activity in vivo was evaluated. Compounds 4a, 4f, and 4k exhibited marked anti-inflammatory activity in LPS-stimulated RAW 264.7 cells. The most promising compound 4k dose-dependently suppressed the cytokines with IC₅₀ values in the low micromolar range. Further, 4k exhibited potential in vitro Nur77-binding affinity (K_d = 6.99 × 10^-6 M) which is consistent with the result of docking studies. Next, the anti-inflammatory mechanism of 4k was found to be through NF-κB signal pathway in a Nur77-dependent manner. Moreover, we also observed 4k significantly inhibited LPS-induced expression of cytokines (IL-6, TNF-α, and IL-1β) through suppressing NF-κB activation and attenuated LPS-induced inflammation in mouse acute lung injury (ALI) model. In conclusion, the study strongly suggests that the PUFA-AA derivatives can be particularly as new Nur77 mediators for further treatment in inflammatory diseases.

  DOI：

  10.1016/j.bioorg.2020.104456

文献信息

• Structure–Activity Relationships of Fish Oil Derivatives with Antiallergic Activity in Vitro and in Vivo
  作者：In-Hae Kim、Yoshiki Kanayama、Hisashi Nishiwaki、Takuya Sugahara、Kosuke Nishi

  DOI：10.1021/acs.jmedchem.9b00994

  日期：2019.11.14

  antiallergic activity in vitro. Ethanolamides of omega-3 fatty acids (α-linolenic acid, EPA, and DHA) were found to possess promising antiallergic activity, whereas free fatty acids and ethanolamides of other fatty acids exhibited no or weak potency. Based on this finding, structure–activity relationships of DHA-ethanolamide (DHEA) derivatives were investigated to yield better fatty acid derivatives with enhanced

  探索了鱼油中的一系列不饱和脂肪酸及其相应的乙醇酰胺代谢物，以发现具有抗过敏活性的活性鱼油成分。发现ω-3脂肪酸的乙醇酰胺（α-亚麻酸，EPA和DHA）具有良好的抗过敏活性，而游离脂肪酸和其他脂肪酸的乙醇酰胺则没有或表现出弱的功效。基于这一发现，研究了DHA-乙醇酰胺（DHEA）衍生物的结构-活性关系，以在体内和体外产生具有增强的抗过敏活性的更好的脂肪酸衍生物。当DHEA的乙醇酰胺部分被取代的磺酰胺官能团取代时，在体外提供了非常有前途的效价。化合物59在体内显示出比DHEA更高的抗过敏活性。结果表明，优化的DHEA衍生物在体内和体外具有增强的抗过敏活性，并且所得结构将成为进一步开发具有良好抗过敏活性的生物利用性衍生物的重要基础。
• [EN] DERIVATIVES OF DOCOSAHEXAENOYLETHANOLAMIDE AND USES THEREOF<br/>[FR] DÉRIVÉS DE DOCOSAHEXAÉNOYLÉTHANOLAMIDE ET SES UTILISATIONS
  申请人：US HEALTH

  公开号：WO2013158302A1

  公开（公告）日：2013-10-24

  The invention provides derivatives of DEA which have increased potency and hydrolysis resistance as compared to DEA, and compositions thereof, as well as methods of using these derivatives to promote neurogenesis, neurite growth and/or length, and/or promote synaptogenesis.

  本发明提供了与DEA相比具有更高效能和更强水解抗性的DEA衍生物及其组成物，以及使用这些衍生物促进神经发生、神经突起生长和/或长度，以及/或促进突触形成的方法。
• Fatty acid guanidine and salicylate guanidine derivatives and their uses
  申请人：Milne Jill C.

  公开号：US09150504B2

  公开（公告）日：2015-10-06

  The invention relates to fatty acid guanidine or salicylate guanidine derivatives; compositions comprising an effective amount of a fatty acid guanidine or salicylate guanidine derivative; and methods for treating or preventing a metabolic disease comprising the administration of an effective amount of a fatty acid guanidine or salicylate guanidine derivative.

  该发明涉及脂肪酸胍或水杨酸胍衍生物；包含有效量的脂肪酸胍或水杨酸胍衍生物的组合物；以及治疗或预防代谢性疾病的方法，包括给予有效量的脂肪酸胍或水杨酸胍衍生物。
• 一种二十二碳六烯酰酯衍生物及其制备方法和应用
  申请人：自然资源部第三海洋研究所

  公开号：CN114853628A

  公开（公告）日：2022-08-05

  本发明公开了一种二十二碳六烯酰酯衍生物及其制备方法和应用，其结构式为其中，n为0‑4的整数，R为或本发明对小鼠巨噬细胞RAW264.7中由脂多糖LPS诱导的促炎性介质的mRNA表达具有一定的下调作用，以及下调一氧化氮NO的外分泌水平，同时，能够抑制促炎性细胞因子的蛋白表达。
• DERIVATIVES OF DOCOSAHEXAENOYLETHANOLAMIDE AND USES THEREOF
  申请人：The United States of America, as Represented by The Secretary, Department of Health and Human Services

  公开号：EP2847178B1

  公开（公告）日：2017-01-04