(2E)-3-(3,4-dihydroxyphenyl)-N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-2-propenamide

• 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: (2E)-3-(3,4-dihydroxyphenyl)-N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-2-propenamide
• 英文别名: caffeic acid 5-methoxytryptamide；(E)-3-(3,4-dihydroxyphenyl)-N-[2-(5-methoxy-1H-indol-3-yl)ethyl]prop-2-enamide
• 化学式: C₂₀H₂₀N₂O₄
• 分子量: 352.39
• InChiKey: XOGFFHVOKMOBGS-XVNBXDOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  94.6
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  在 一水合肼 作用下， 生成 (2E)-3-(3,4-dihydroxyphenyl)-N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-2-propenamide
  参考文献：
  名称：

  N-[(Dihydroxyphenyl)acyl]serotonins as potent inhibitors of tyrosinase from mouse and human melanoma cells

  摘要：

  A series of N-acyl derivatives of tyramine, tryptamine, and serotonin were synthesized and tested on anti-melanogenic activity. The serotonin derivatives such as N-caffeoylserotonin (3) and N-protocatechuoylserotonin (9) were inhibitory to tyrosinase from mouse B16 and human HMV-II melanoma cells, while the corresponding derivatives of tryptamine and 5-methoxytryptamine were almost inactive or less active than the serotonin derivatives. The inhibitory activity of the serotonin derivatives increased with increasing number of phenolic hydroxyl groups in the acyl moiety. Melanin formation in the culture of B16 cells was suppressed by 3 and 9 with no cytotoxicity in the concentration range tested (IC50 = 15, 3 and 111 mu M for 3, 9, and kojic acid, respectively). Thus the N-acylserotonin derivatives having a dihydroxyphenyl group are potential anti-melanogenic agents. Their inhibition of tyrosinase is primarily performed through the 5-hydroxyindole moiety and further strengthened by the phenolic hydroxyl groups in the acyl moiety. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.05.115

文献信息

• Indole derivatives
  申请人：Zisapel Nava

  公开号：US06858642B1

  公开（公告）日：2005-02-22

  The invention relates to 1-(R 1 )-2-(R 2 )-3-(Y-X—NH-A- or Z-A-)-4,5,6,7-R) 0.4 -indoles, and their acid addition salts where the compounds are basic, wherein A is C 1-4 alkylene, X is >CH 2 , >C═O or >C═S, and the other symbols have various defined values, and to pharmaceutical, skin-protective and cosmetic compositions which comprise them.

  该发明涉及1-(R1)-2-(R2)-3-(Y-X—NH-A-或Z-A-)-4,5,6,7-R)0.4-吲哚类化合物及其酸盐，其中这些化合物是碱性的，其中A是C1-4烷基，X是>CH2，>C═O或>C═S，其他符号具有各自定义的值，并涉及包括这些化合物的药用、皮肤保护和化妆品组合物。
• COSMETIC COMPOSITION FOR STIMULATING THE CELLULAR ANTI-AGING FUNCTIONS OF THE SKIN
  申请人：SYNTIVIA

  公开号：US20150031740A1

  公开（公告）日：2015-01-29

  The use of a compound of general formula (I), where: R 1 , R 2 , R 3 , R 4 , R 5 are identical or different and each represent a hydrogen atom, a halogen atom, a hydroxyl group or an —OR′ radical in which R′ is a straight or branched, saturated or unsaturated C1-C16 hydrocarbon radical, wherein at least one group from among R 1 , R 2 , R 3 , R 4 , and R 5 does not represent a hydrogen atom or a halogen atom; X is a halogen atom, a hydroxyl group, a nitro group, a straight or branched, saturated or unsaturated optionally substituted C1-C14 hydrocarbon radical, or an —OR″ radical in which R″ is a straight or branched, saturated or unsaturated optionally substituted C1-C14 hydrocarbon radical; and Z is a covalent bond or a spacer arm, or of one of the salts thereof, in a cosmetic composition for stimulating the cellular anti-aging functions of the skin.

  使用通式（I）的化合物，其中：R1、R2、R3、R4、R5相同或不同，每个代表氢原子、卤素原子、羟基或—OR′基团，其中R′是直链或支链、饱和或不饱和的C1-C16烃基基团，其中至少一个来自于R1、R2、R3、R4和R5的基团不代表氢原子或卤素原子；X是卤素原子、羟基、硝基、直链或支链、饱和或不饱和的可选取代的C1-C14烃基基团，或—OR″基团，其中R″是直链或支链、饱和或不饱和的可选取代的C1-C14烃基基团；Z是共价键或间隔臂，或其盐之一，在化妆品配方中用于刺激皮肤的细胞抗衰老功能。
• COMPOSITION COSMÉTIQUE POUR STIMULER LES FONCTIONS CELLULAIRES ANTI-VIEILLISSEMENT DE LA PEAU
  申请人：Syntivia

  公开号：EP2790659B1

  公开（公告）日：2017-03-01
• US7355054B2
  申请人：——

  公开号：US7355054B2

  公开（公告）日：2008-04-08
• [EN] COSMETIC COMPOSITION FOR STIMULATING THE CELLULAR ANTI-AGING FUNCTIONS OF THE SKIN<br/>[FR] COMPOSITION COSMÉTIQUE POUR STIMULER LES FONCTIONS CELLULAIRES ANTI-VIEILLISSEMENT DE LA PEAU
  申请人：SYNTIVIA

  公开号：WO2013087834A2

  公开（公告）日：2013-06-20

  L'invention concerne l'utilisation d'un composé de formule générale (I) dans laquelle R1, R2, R3, R4, R5 identiques ou différents, représentent chacun un atome d'hydrogène, un atome d'halogène, un groupement hydroxyle ou un radical –OR' où R' représente un radical hydrocarboné linéaire ou ramifié, saturé ou insaturé, en C1-C16, au moins un groupement parmi R1, R2, R3, R4 et R5 ne représentant pas un atome d'hydrogène ou un atome d'halogène; X représente un atome d'halogène, un groupement hydroxyle, un groupement nitro, un radical hydrocarboné linéaire ou ramifié, saturé ou insaturé, éventuellement substitué, en C1-C14, ou un radical –OR'' où R'' représente un radical hydrocarboné linéaire ou ramifié, saturé ou insaturé, éventuellement substitué, en C1-C14; Z représente une liaison covalente ou un bras espaceur, ou un de ses sels, dans une composition cosmétique pour stimuler les fonctions cellulaires anti- vieillissement de la peau.