N-trans-feruloyldopamine | 142350-99-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: N-trans-feruloyldopamine
• 英文别名: trans-N-feruloyldopamine；N-Feruloyl dopamine, trans-；(E)-N-[2-(3,4-dihydroxyphenyl)ethyl]-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamide
• CAS: 142350-99-0
• 化学式: C₁₈H₁₉NO₅
• 分子量: 329.353
• InChiKey: ZRLYUFOWFPPSTD-QPJJXVBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  99
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  acetyl ferulic acid 在 sodium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 2.0h， 生成 N-trans-feruloyldopamine
  参考文献：
  名称：

  Inhibition of in Vitro Prostaglandin and Leukotriene Biosyntheses by Cinnamoyl-.BETA.-phenethylamine and N-Acyldopamine Derivatives.

  摘要：

  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。

  DOI：

  10.1248/cpb.40.396

文献信息

• Para-coumaric acid or para-hydroxycinnamic acid derivatives and their use in cosmetic or dermatological compositions
  申请人：Okombi Sabrina

  公开号：US20070183996A1

  公开（公告）日：2007-08-09

  The invention relates to the use of para-coumaric acid or para-hydroxycinnamic acid derivatives in cosmetic or dermatological compositions, specifically to the use of at least one compound derived from para-coumaric acid having a general formula (I) below: in which, especially, Z represents an oxygen or an —NH— group; X and Y are identical and each represent a CH or CH 2 group, as an active principle with depigmenting, free-radical-scavenging and/or antiinflammatory activity. The invention also relates to the use of the above compounds for cosmetic care or for the preparation of a pharmaceutical composition, especially for depigmenting an area of skin, having antiradical and/or antiinflammatory activity.

  该发明涉及对苯对羟基肉桂酸或对羟基肉桂酸衍生物在化妆品或皮肤科学组合物中的使用，具体地涉及至少一种源自苯对羟基肉桂酸的化合物的使用，其具有下面的一般式(I)：其中，特别地，Z代表氧原子或—NH—基团；X和Y相同，各代表一个CH或CH2基团，作为具有脱色、自由基清除和/或抗炎活性的活性原理。该发明还涉及上述化合物在化妆护理或制备药用组合物中的使用，特别是用于脱色皮肤区域，具有抗自由基和/或抗炎活性。
• Synthesis of Amide and Ester Derivatives of Cinnamic Acid and Its Analogs: Evaluation of Their Free Radical Scavenging and Monoamine Oxidase and Cholinesterase Inhibitory Activities
  作者：Koichi Takao、Kazuhiro Toda、Takayuki Saito、Yoshiaki Sugita

  DOI：10.1248/cpb.c17-00416

  日期：——

  and selective MAO-B inhibitory activity. Compound 20 was the most potent inhibitor of MAO-B. Compounds 18 and 21 showed moderate BChE inhibitory activity. In addition, compound 18 showed potent antioxidant activity and MAO-B inhibitory activity. In a comparison of the cinnamic acid amides and esters, the amides exhibited more potent DPPH free radical scavenging activity, while the esters showed stronger

  合成了一系列肉桂酸衍生物，酰胺（1-12）和酯（13-22），并建立了抗氧化活性与单胺氧化酶（MAO）A和B，乙酰胆碱酯酶和丁酰胆碱酯酶（BChE）的构效关系。分析抑制活性。在合成的化合物中，化合物1-10、12-18和迷迭香酸（23）含有邻苯二酚，邻甲氧基苯酚或5-羟基吲哚部分，它们显示出有效的1,1-二苯基-2-吡啶并肼基（DPPH）自由基清除活动。化合物9-11、15、17-22显示出有效和选择性的MAO-B抑制活性。化合物20是最有效的MAO-B抑制剂。化合物18和21显示出中等的BChE抑制活性。另外，化合物18显示出有效的抗氧化剂活性和MAO-B抑制活性。在肉桂酸酰胺和酯的比较中，酰胺表现出更强的DPPH自由基清除活性，而酯显示出对MAO-B和BChE的较强抑制活性。这些结果表明，肉桂酸衍生物，例如化合物18，对香豆酸3,4-二羟基苯乙基酯，和化合物20，对香豆酸苯乙酯，可以用
• NOVEL DERIVATIVES OF SINAPINIC ACID AND THE COSMETIC OR PHARMACEUTICAL USES THEREOF
  申请人：BASF Beauty Care Solutions France SAS

  公开号：US20150342847A1

  公开（公告）日：2015-12-03

  The present invention relates to a compound of general formula (I) below: in which: R 1 , R 2 and R 3 independently of one another represent a hydrogen atom; a C1-12 alkyl group; a C2-12 alkenyl group; a C2-12 alkynyl group; a C3-12 cycloalkyl group; a C1-12 acyl group; a sulfonyl group or a phosphonate group; represents a CH 2 —CH 2 group or a CH═CH group; n is an integer between 1 and 3; or a salt thereof. The invention further relates to a process for synthesizing this compound or salt, to a composition comprising it, to its cosmetic use, more particularly as a depigmenting agent and/or as a radical scavenger, to a cosmetic care process, and to its use as a drug, advantageously intended for preventing and/or treating pathological hyperpigmentation and/or inflammation.

  本发明涉及以下一般式（I）的化合物： 其中： R1、R2和R3分别独立地表示氢原子；C1-12烷基基团；C2-12烯基基团；C2-12炔基基团；C3-12环烷基基团；C1-12酰基团；磺酰基或膦酸酯基团；表示CH2—CH2基团或CH═CH基团；n是1到3之间的整数；或其盐。该发明还涉及合成该化合物或盐的过程，包括它的组合物，其化妆品用途，尤其作为脱色剂和/或自由基清除剂，化妆保养过程，以及其作为药物的用途，有利于预防和/或治疗病理性色素沉着和/或炎症。
• Induction of<i>N</i>-Hydroxycinnamoyltyramine Synthesis and Tyramine<i>N</i>-Hydroxycinnamoyltransferase (THT) Activity by Wounding in Maize Leaves
  作者：Atsushi ISHIHARA、Naoki KAWATA、Tetsuya MATSUKAWA、Hajime IWAMURA

  DOI：10.1271/bbb.64.1025

  日期：2000.1

  Both N-p-coumaroyl- and N-feruloyltyramine accumulated in response to wounding in leaf segments of maize. The amount of N-hydroxycinnamoyltyramines started to increase 3-6 h after wounding and peaked at 12 h. Thereafter, the amount of N-p-coumaroyltyramine decreased rapidly, while the N-feruloyltyramine content remained at a high level. The accumulation of N-hydroxycinnamoyltyramines was accompanied by an increase in the tyramine N-hydroxycinnamoyltransferase (THT) activity. This increase was initially detected 3 h after wounding and reached a maximum at 36 h, the level of activity being 40 and 11 times that in the leaves before wounding and in the control leaves, respectively. Partial purification of THT from wounded leaves by (NH4)2SO4 precipitation and subsequent two steps of anion-exchange chromatography resulted in a 12.5-fold increase in specific activity. Kinetic studies with this partially purified enzyme revealed that the best substrates were tyramine and feruloyl-CoA, although tryptamine and sinapoyl-CoA also efficiently served as substrates. The apparent native molecular weight of the enzyme was determined by gel filtration as 40 kDa.

  玉米叶片受伤后，N-对香豆酰基和 N-阿魏酰基酪胺都会积累。受伤后 3-6 小时，N-羟基肉桂酰基酪胺的含量开始增加，12 小时达到峰值。此后，N-对香豆酰基酪胺的含量迅速下降，而 N-阿魏酰基酪胺的含量则保持在较高水平。伴随着 N-羟基肉桂酰基酪胺的积累，酪胺 N-羟基肉桂酰基转移酶（THT）的活性也在增加。这种增加最初是在受伤 3 小时后发现的，并在 36 小时后达到最大值，其活性水平分别是受伤前叶片和对照叶片的 40 倍和 11 倍。通过（NH4）2SO4 沉淀和随后的两步阴离子交换色谱法对受伤叶片中的 THT 进行部分纯化后，比活性提高了 12.5 倍。对这种部分纯化的酶进行的动力学研究表明，最佳底物是酪胺和阿魏酰-CoA，尽管色胺和山奈酰-CoA 也能有效地作为底物。经凝胶过滤测定，该酶的表观原生分子量为 40 kDa。
• Synthesis of phenolic amides and evaluation of their antioxidant and anti-inflammatory activity in vitro and in vivo
  作者：Ya-Ting Lee、You-Liang Hsieh、Yen-Hung Yeh、Chih-Yang Huang

  DOI：10.1039/c5ra14137k

  日期：——

  15 phenolic amides (PAs) have been synthesized and examinedin vitrousing four tests: (1) prevention of Cu²⁺-induced human low-density lipoprotein oxidation, (2) scavenging of stable radicals, (3) anti-inflammatory activity, and (4) scavenging of superoxide radicals.

  已合成和检验了15种酚酰胺（PAs），使用四种测试方法：in vitro（1）预防Cu²⁺诱导的人类低密度脂蛋白氧化，（2）稳定自由基清除，（3）抗炎活性和（4）清除超氧自由基。