N-(3,4-bisacetoxyphenethyl)octanamide | 1426393-07-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: N-(3,4-bisacetoxyphenethyl)octanamide
• 英文别名: 4-(2-octanamidoethyl)-1,2-phenylene diacetate；A-NOD；N-(3,4-bisacetoxyphenylethyl)octanamide；[2-acetyloxy-4-[2-(octanoylamino)ethyl]phenyl] acetate
• CAS: 1426393-07-8
• 化学式: C₂₀H₂₉NO₅
• 分子量: 363.454
• InChiKey: VCWQPKPJFKGOSV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  26
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (乙基碳酸)辛酸酐 在 硫酸 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 N-(3,4-bisacetoxyphenethyl)octanamide
  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

• [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。
• Analyses of Synthetic <i>N</i>-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
  作者：Prama Pallavi、Marc Pretze、Julio Caballero、Yingchun Li、Björn B. Hofmann、Eleni Stamellou、Sarah Klotz、Carmen Wängler、Björn Wängler、Ralf Loesel、Steffen Roth、Bastian Theisinger、Handan Moerz、Uta Binzen、Wolfgang Greffrath、Rolf-Detlef Treede、Martin C. Harmsen、Bernhard K. Krämer、Mathias Hafner、Benito A. Yard、Anna-Isabelle Kälsch

  DOI：10.1021/acs.jmedchem.8b00156

  日期：2018.4.12

  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.