N-feruloyl serotonin | 1246613-20-6

• 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: N-feruloyl serotonin
• 英文别名: N-Dihydroferuloyl serotonin；N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-3-(4-hydroxy-3-methoxyphenyl)propanamide
• CAS: 1246613-20-6
• 化学式: C₂₀H₂₂N₂O₄
• 分子量: 354.406
• InChiKey: MQTQTYNXVBXXBT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  3-(4-羟基-3-甲氧基苯基)丙酸 、 5-羟基色胺盐酸盐 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 以85%的产率得到N-feruloyl serotonin
  参考文献：
  名称：

  Synthesis and structure–activity relationships of serotonin derivatives effect on α-glucosidase inhibition

  摘要：

  The alpha-glucosidase inhibitory activities of serotonin derivatives were evaluated. Two serotonin derivatives, N-p-coumaroyl serotonin (2) and N-caffeoyl serotonin (4) exhibited most potent inhibition on alpha-glucosidase, whereas, cinnamic acid derivatives were less efficient. Furthermore, we analyzed their structural importance for alpha-glucosidase inhibition. The linkage of cinnamic acid moiety and serotonin moiety and the olefin in cinnamic acid moiety of serotonin derivatives were crucial for alpha-glucosidase inhibition. This is the first report on structure-activity relationships (SAR) for the alpha-glucosidase inhibitory activity of serotonin derivatives.

  DOI：

  10.1007/s00044-011-9699-9

文献信息

• 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
• 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.
• US20140255327A1
  申请人：——

  公开号：US20140255327A1

  公开（公告）日：2014-09-11
• US9295624B2
  申请人：——

  公开号：US9295624B2

  公开（公告）日：2016-03-29