3-adamantan-1-yl-N-[2-(3,4-dihydroxyphenyl)-ethyl]-4-hydroxy-benzoic acid amide | 1422043-88-6

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 石蒜科生物碱
• 英文名称: 3-adamantan-1-yl-N-[2-(3,4-dihydroxyphenyl)-ethyl]-4-hydroxy-benzoic acid amide
• 英文别名: 3-adamantan-1-yl-N-[2-(3,4-dihydroxyphenyl)ethyl]-4-hydroxybenzamide；3-(1-adamantyl)-N-[2-(3,4-dihydroxyphenyl)ethyl]-4-hydroxybenzamide
• CAS: 1422043-88-6
• 化学式: C₂₅H₂₉NO₄
• 分子量: 407.51
• InChiKey: GBULPMULSUQYGY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  89.8
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  对羟基苯甲酸 在 硫酸 、 碳酸氢钠 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 反应 12.0h， 生成 3-adamantan-1-yl-N-[2-(3,4-dihydroxyphenyl)-ethyl]-4-hydroxy-benzoic acid amide
  参考文献：
  名称：

  3D-QSAR study of adamantyl N-benzylbenzamides as melanogenesis inhibitors

  摘要：

  Three-dimensional quantitative structure-activity relationship (3D-QSAR) modeling, comparative molecular field analysis (CoMFA), and comparative molecular similarity indices analysis (CoMSIA) of polyhydroxylated N-benzylbenzamide derivatives containing an adamantyl moiety were performed to understand the mechanism of action and structure-activity relationship of these compounds. Contour map analysis indicated that steric contributions of the adamantyl moiety and electrostatic contributions of the hydroxyl group at the 3-position are important in the activity. Activities of the training set and test sets predicted by CoMFA fit well with actual activities, demonstrating that CoMFA, along with the best calculated q(2) value, has the best predictive ability. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.11.056

文献信息

• NOVEL BENZOIC ACID AMIDE COMPOUND
  申请人：Joo Yung Hyup

  公开号：US20140234241A1

  公开（公告）日：2014-08-21

  The present invention relates to a novel benzoic acid amide derivative compound, isomers thereof, pharmaceutically acceptable salts thereof, prodrugs thereof, hydrates thereof, or solvates thereof. The novel compound has excellent skin whitening effects.

  本发明涉及一种新型苯甲酸酰胺衍生物化合物，其同分异构体，其药用可接受的盐，其前药，其水合物，或其溶剂化合物。这种新型化合物具有出色的美白皮肤效果。
• COMPOSITION COMPRISING BENZOIC ACID AMIDE COMPOUND AND CYCLODEXTRIN SOLUBILIZING AGENT
  申请人：Amorepacific Corporation

  公开号：EP3610865A1

  公开（公告）日：2020-02-19

  The present specification relates to a composition for external application to skin with improved solubility and feeling during use, comprising a benzoic acid amide compound, an isomer thereof, a pharmaceutically acceptable salt thereof, a hydrate thereof or a solute that is a solvate thereof, and a first cyclodextrin solubilizing agent.

  本说明书涉及一种用于皮肤外用的组合物，该组合物在使用过程中具有更好的溶解性和感觉，包括苯甲酸酰胺化合物、其异构体、其药学上可接受的盐、其水合物或其溶解物，以及第一环糊精增溶剂。
• US9254251B2
  申请人：——

  公开号：US9254251B2

  公开（公告）日：2016-02-09
• 3D-QSAR study of adamantyl N-benzylbenzamides as melanogenesis inhibitors
  作者：Yong Deog Hong、Heung Soo Baek、Haelim Cho、Soo Mi Ahn、Ho Sik Rho、Young-Ho Park、Yung Hyup Joo、Song Seok Shin

  DOI：10.1016/j.bmcl.2013.11.056

  日期：2014.1

  Three-dimensional quantitative structure-activity relationship (3D-QSAR) modeling, comparative molecular field analysis (CoMFA), and comparative molecular similarity indices analysis (CoMSIA) of polyhydroxylated N-benzylbenzamide derivatives containing an adamantyl moiety were performed to understand the mechanism of action and structure-activity relationship of these compounds. Contour map analysis indicated that steric contributions of the adamantyl moiety and electrostatic contributions of the hydroxyl group at the 3-position are important in the activity. Activities of the training set and test sets predicted by CoMFA fit well with actual activities, demonstrating that CoMFA, along with the best calculated q(2) value, has the best predictive ability. (C) 2013 Elsevier Ltd. All rights reserved.