N-(2-(1H-indol-3-yl)ethyl)-4-hydroxybenzamide | 1186309-93-2

• 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-(2-(1H-indol-3-yl)ethyl)-4-hydroxybenzamide
• 英文别名: 4-hydroxy-N-[2-(1H-indol-3-yl)ethyl]benzamide
• CAS: 1186309-93-2
• 化学式: C₁₇H₁₆N₂O₂
• 分子量: 280.326
• InChiKey: MLKONJPJJSFXFY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 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：
  65.1
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(2-(1H-indol-3-yl)ethyl)-4-hydroxybenzamide 在 potassium carbonate 、 potassium iodide 作用下， 以 丙酮 、 乙腈 、 Petroleum ether 为溶剂， 反应 96.0h， 生成 N-[2-(1H-indol-3-yl)ethyl]-4-(4-quinolin-1-ium-1-ylbutoxy)benzamide;bromide
  参考文献：
  名称：

  Design, synthesis, and bioevaluation of benzamides: Novel acetylcholinesterase inhibitors with multi-functions on butylcholinesterase, Aβ aggregation, and β-secretase

  摘要：

  Alzheimer's disease (AD) is a multifactorial syndrome with several target proteins contributing to its etiology. In this study, we conducted a structure-based design and successfully produced a series of new multi-site AChE inhibitors with a novel framework. Compound 2e, characterized by a central benzamide moiety linked to an isoquinoline at one side and acetophenone at the other, was the most potent candidate with K-i of 6.47 nM against human AChE. Particularly, it showed simultaneous inhibitory effects against BChE, A beta aggregation, and beta-secretase. We therefore conclude that compound 2e is a very promising multi-function lead for the treatment of AD. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.09.016
• 作为产物：
  描述：

  [4-[2-(1H-indol-3-yl)ethylcarbamoyl]phenyl] acetate 在 一水合肼 作用下， 生成 N-(2-(1H-indol-3-yl)ethyl)-4-hydroxybenzamide
  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。
• 10.1021/jacs.4c06421
  作者：Yamada, Kyohei、Cheung, Kelvin Pak Shing、Gevorgyan, Vladimir

  DOI：10.1021/jacs.4c06421

  日期：——

  photocatalytic platform as a general solution to these problems, enabling the coupling of diverse internal alkenes with carboxylic acids, alcohols, and other O-nucleophiles, typically in a highly regio- and diastereoselective manner.

  支链烯丙酯和羧酸酯是天然产物和药物分子中普遍存在的基本基序。内部烯烃的直接烯丙基 C-H 氧化代表了最直接的方法之一，绕过了经典 Tsuji-Trost 反应中对烯丙基离去基团的要求。然而，目前的方法范围有限（通常伴随着选择性问题），从而阻碍了进一步的发展。在此，我们报告了一种光催化平台作为这些问题的通用解决方案，能够将不同的内烯烃与羧酸、醇和其他O-亲核试剂偶联，通常以高度区域选择性和非对映选择性的方式。
• 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
• [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.
• Design, synthesis, and bioevaluation of benzamides: Novel acetylcholinesterase inhibitors with multi-functions on butylcholinesterase, Aβ aggregation, and β-secretase
  作者：Da-Yong Peng、Qi Sun、Xiao-Lei Zhu、Hong-Yan Lin、Qiong Chen、Ning-Xi Yu、Wen-Chao Yang、Guang-Fu Yang

  DOI：10.1016/j.bmc.2012.09.016

  日期：2012.11

  Alzheimer's disease (AD) is a multifactorial syndrome with several target proteins contributing to its etiology. In this study, we conducted a structure-based design and successfully produced a series of new multi-site AChE inhibitors with a novel framework. Compound 2e, characterized by a central benzamide moiety linked to an isoquinoline at one side and acetophenone at the other, was the most potent candidate with K-i of 6.47 nM against human AChE. Particularly, it showed simultaneous inhibitory effects against BChE, A beta aggregation, and beta-secretase. We therefore conclude that compound 2e is a very promising multi-function lead for the treatment of AD. (C) 2012 Elsevier Ltd. All rights reserved.