(E)-N-(3,4-dihydroxybenzyl)-8-methylnon-6-enamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (E)-N-(3,4-dihydroxybenzyl)-8-methylnon-6-enamide
• 英文别名: 8-methyl-N-[(3,4-dihydroxyphenyl)-methyl]-(trans)-6-nonenylamide；CAPSAICIN_met007；(E)-N-[(3,4-dihydroxyphenyl)methyl]-8-methylnon-6-enamide
• 化学式: C₁₇H₂₅NO₃
• 分子量: 291.39
• InChiKey: BZSMUIBFQYJFOC-FNORWQNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  烟酸 、 (E)-N-(3,4-dihydroxybenzyl)-8-methylnon-6-enamide 在 氯化亚砜 作用下， 反应 10.0h， 以48.8%的产率得到8-methyl-N-[(3-hydroxy-4-nicotinate phenyl)-methyl]-(trans)-6-nonenylamide
  参考文献：
  名称：

  含烟酸辣椒碱酯衍生物、制备方法及其用途

  摘要：

  本发明提供了一类具有结构通式I的含烟酸辣椒碱酯衍生物及其制造方法，及此类衍生物具有镇痛、抗肿瘤、抗炎、抗动脉粥样硬化、降血脂、促进食欲、改善消化、抗菌杀虫、抗氧化、抗病毒方面的用途。

  公开号：

  CN108069898B
• 作为产物：
  描述：

  辣椒碱 在 三溴化硼 、 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 1.08h， 以29%的产率得到(E)-N-(3,4-dihydroxybenzyl)-8-methylnon-6-enamide
  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

• CAPSAICINOID DECONTAMINATION COMPOSITIONS AND METHODS OF USE
  申请人：Reilly Christopher A.

  公开号：US20100086626A1

  公开（公告）日：2010-04-08

  A therapeutic composition for inhibiting physiological responses elicited by exposure of skin to an irritant can be used to treat exposure to capsaicinoids or other chemical irritants. The therapeutic composition can include a carrier being present in an effective amount and form sufficient to be applied to skin and deliver active agents to the skin which has been previously exposed to a capsaicinoid. Also, the therapeutic composition can include a cooling agent in an effective amount within the carrier to provide a cooling sensation to the skin. Further, the therapeutic composition can include a capsaicin receptor antagonist in an effective amount within the carrier to inhibit calcium flux associated with activation of the capsaicin receptor by a capsaicinoid. The therapeutic composition can be part of a kit that also includes a cleansing composition, which is capable of cleaning and/or absorbing capsaicinoids from the skin.
• 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.
• 含烟酸辣椒碱酯衍生物、制备方法及其用途
  申请人：南华大学

  公开号：CN108069898B

  公开（公告）日：2021-11-23

  本发明提供了一类具有结构通式I的含烟酸辣椒碱酯衍生物及其制造方法，及此类衍生物具有镇痛、抗肿瘤、抗炎、抗动脉粥样硬化、降血脂、促进食欲、改善消化、抗菌杀虫、抗氧化、抗病毒方面的用途。