3,4-dihydroxy-N-[2-(5-hydroxyindol-3-yl)ethyl]benzamide | 1186309-90-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 3,4-dihydroxy-N-[2-(5-hydroxyindol-3-yl)ethyl]benzamide
• 英文别名: N-(3,4-dihydroxybenzoyl)serotonin；N-protocatechuoylserotonin；3,4-dihydroxy-N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]benzamide
• CAS: 1186309-90-9
• 化学式: C₁₇H₁₆N₂O₄
• 分子量: 312.325
• InChiKey: UYVJAIZMSPRFQW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  106
• 氢给体数：
  5
• 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 3,4-dihydroxy-N-[2-(5-hydroxyindol-3-yl)ethyl]benzamide
  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

• 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。
• NOVEL AMIDE DERIVATIVE AND WHITENING AGENT
  申请人：AMINO Yusuke

  公开号：US20120070395A1

  公开（公告）日：2012-03-22

  Compound represented by formula (I): wherein the symbols are as defined in the description, and salts thereof, are useful as skin whitening agents.

  式（I）所代表的化合物：其中符号如描述中定义的那样，以及其盐，可用作皮肤美白剂。
• NOVEL AMIDE DERIVATIVE AND SKIN WHITENING AGENT
  申请人：Ajinomoto Co., Inc.

  公开号：EP2412701B1

  公开（公告）日：2015-08-12
• 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
• SALTY TASTE ENHANCER
  申请人：AJINOMOTO CO., INC.

  公开号：US20130196050A1

  公开（公告）日：2013-08-01

  Compounds represented by formula (I): wherein each symbol is as defined in the specification, exhibit a salty taste enhancing activity and are useful as salty taste enhancers for foods and drinks.