3-(3-羟基苯基)苯甲酰胺 | 681161-44-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-(3-羟基苯基)苯甲酰胺
• 中文别名: 3-羟基-[1,1-联苯]-3-羧酰胺
• 英文名称: 3-(3-hydroxyphenyl)benzamide
• 英文别名: 3'-hydroxybiphenyl-3-carboxylic acid amide；3'-Hydroxy-[1,1'-biphenyl]-3-carboxamide
• CAS: 681161-44-4
• 化学式: C₁₃H₁₁NO₂
• 分子量: 213.236
• InChiKey: BQRRGDDGUKOPJO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  63.3
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2924299090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319

反应信息

• 作为反应物：
  描述：

  3-(3-羟基苯基)苯甲酰胺 在 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 5.0h， 生成 3′-carbamoyl-[1,1′-biphenyl]-3-yl N-{6-[3-((2-acetamidoethyl)methylamino)phenoxy]hexyl} carbamate
  参考文献：
  名称：

  Identification of Bivalent Ligands with Melatonin Receptor Agonist and Fatty Acid Amide Hydrolase (FAAH) Inhibitory Activity That Exhibit Ocular Hypotensive Effect in the Rabbit

  摘要：

  Activation of melatonin receptors and inhibition of fatty acid amide hydrolase (FAAH) have both shown potential benefits for the treatment of glaucoma. To exploit the combination of these biological activities in single therapeutic agents, we designed dual-acting compounds sharing the pharmacophore elements required for the two targets, in search for balanced potencies as MT1/MT2 agonists and FAAH inhibitors. In particular, the N-anilinoethylamide scaffold, previously developed for melatonergic ligands, was decorated at meta position with a polymethylene linker bound to an O-arylcarbamate group, substituted according to known structure-activity relationships for FAAH inhibition. For the most active series, the N-anilinoethylamide portion was also replaced with the indole scaffold of melatonin. O-Biphenyl-3-ylcarbamate characterized by remarkable and balanced activity at both targets, in the nanomolar range for compound 29. Topical administration reduced elevated intraocular pressure in rabbits, with a longer action and improved efficacy compared to the reference compounds melatonin and URB597.

  DOI：

  10.1021/acs.jmedchem.8b00893
• 作为产物：
  描述：

  5'-oxo-2',3',4',5'-tetrahydro-[1,1'-biphenyl]-3-carboxamide 在 tetrakis(acetonitrile)palladium(II) bis(tetrafluoroborate) 、 6,6'-二甲基-2,2'-联吡啶 、 sodium anthraquinone-2-sulfonate 、 氧气 作用下， 以 水 、 二甲基亚砜 为溶剂， 80.0 ℃ 、101.33 kPa 条件下， 反应 24.0h， 以88%的产率得到3-(3-羟基苯基)苯甲酰胺
  参考文献：
  名称：

  环己烯酮的有氧氧化 Heck/脱氢反应：有效获得间位取代酚

  摘要：

  争夺（间）位：一种新型双阳离子钯（II）催化剂，采用 6,6'-二甲基-2,2'-联吡啶配体，促进环己烯酮的有氧氧化 Heck 偶联和脱氢反应。这些反应可以以一锅法顺序组合，以实现间位取代酚的直接合成（参见方案）。

  DOI：

  10.1002/anie.201209457

文献信息

• METHOD OF TREATMENT USING NOVEL ANTAGONISTS OR INVERSE AGONISTS AT OPIOID RECEPTORS
  申请人：IGNAR DIANE MICHELE

  公开号：US20100113512A1

  公开（公告）日：2010-05-06

  A method of treatment using pharmaceutical compositions containing novel antagonists or inverse agonists at opioid receptors for the treatment of binge eating disorder, anorexia nervosa, bulimia nervosa, excess drug or alcohol use, or eating disorder not otherwise specified.

  使用含有新型阿片受体拮抗剂或反向激动剂的药物组合物治疗暴食症、厌食症、暴食症、过度药物或酒精使用或其他未明确指定的进食障碍的治疗方法。
• [EN] PHENYL CARBAMATES AND THEIR USE AS INHIBITORS OF THE FATTY ACID AMIDE HYDROLASE (FAAH) ENZYME AND MODULATORS OF THE D3 DOPAMINE RECEPTOR (D3DR)<br/>[FR] PHENYL CARBAMATES ET LEUR UTILISATION COMME INHIBITEURS DE L'ENZYME HYDROLASE D'AMIDES D'ACIDES GRAS (FAAH) ET MODULATEURS DU RÉCEPTEUR D3 DE LA DOPAMINE (D3DR)
  申请人：FOND ISTITUTO ITALIANO DI TECNOLOGIA

  公开号：WO2015007615A1

  公开（公告）日：2015-01-22

  The invention provides compounds of Formula (I) or pharmaceutically acceptable salts thereof wherein Ar', R1, R2, R3, R4, X, Y are as defined in the description of invention, as multi-target directed ligands (MTDLs) that are at the same time inhibitors of the fatty acid amide hydrolase (FAAH) enzyme and modulators of the D3 dopamine receptor (D3DR), their methods of preparation, formulations and therapeutic applications thereof.

  该发明提供了式（I）的化合物或其药用可接受的盐，其中Ar'，R1，R2，R3，R4，X，Y如发明描述中所定义，作为多靶点定向配体（MTDLs），同时是脂肪酸酰胺水解酶（FAAH）酶的抑制剂和D3多巴胺受体（D3DR）的调节剂，以及它们的制备方法、配方和治疗应用。
• NOVEL COMPOUNDS AS ANTAGONISTS OR INVERSE AGONISTS AT OPIOID RECEPTORS
  申请人：Cowan David John

  公开号：US20110124559A1

  公开（公告）日：2011-05-26

  Novel compounds which are antagonists or inverse agonists at one or more of the opioid receptors, pharmaceutical compositions containing them, to processes for their preparation.

  小说化合物，它们是阿片受体的拮抗剂或逆向激动剂，含有它们的药物组合物，以及它们的制备方法。
• Design, Synthesis, Structure–Activity Relationship Studies, and Three-Dimensional Quantitative Structure–Activity Relationship (3D-QSAR) Modeling of a Series of <i>O</i>-Biphenyl Carbamates as Dual Modulators of Dopamine D3 Receptor and Fatty Acid Amide Hydrolase
  作者：Alessio De Simone、Debora Russo、Gian Filippo Ruda、Alessandra Micoli、Mariarosaria Ferraro、Rita Maria Concetta Di Martino、Giuliana Ottonello、Maria Summa、Andrea Armirotti、Tiziano Bandiera、Andrea Cavalli、Giovanni Bottegoni

  DOI：10.1021/acs.jmedchem.6b01578

  日期：2017.3.23

  rationalized the structural features conducive to activities at the main targets and investigated activities at two off-targets: dopamine receptor subtype D2 and endocannabinoid receptor CB1. To understand the unexpected affinity for the CB1 receptor, we devised a 3D-QSAR model, which we then prospectively validated. Compound 33 was selected for PK studies because it displayed balanced affinities for the main

  我们最近报道了根据多靶标定向配体范例设计的分子，以对人脂肪酸酰胺水解酶（FAAH）和多巴胺受体D3亚型（D3R）发挥联合活性。这两个目标都与解决几种类型的成瘾（最著名的是尼古丁成瘾）和其他强迫行为有关。在这里，我们报告了一系列联苯-N- [4- [4-（4-（2,3-取代-苯基）哌嗪-1-基]烷基]氨基甲酸酯的SAR勘探，这是一类新颖的分子，已显示出有希望的活性在FAAH–D3R目标组合中进行初步研究。我们已经合理化了有利于主要目标活动的结构特征，并研究了两个非目标活动：多巴胺受体D2亚型和内源性大麻素受体CB 1。为了了解对CB 1受体的意外亲和力，我们设计了一个3D-QSAR模型，然后对其进行了前瞻性验证。选择化合物33进行PK研究是因为它对主要靶标显示出平衡的亲和力，并且在两个非靶标上均具有明显的选择性。33具有良好的稳定性和口服生物利用度，可以穿越血脑屏障。
• Applying a multitarget rational drug design strategy: the first set of modulators with potent and balanced activity toward dopamine D3 receptor and fatty acid amide hydrolase
  作者：Alessio De Simone、Gian Filippo Ruda、Clara Albani、Glauco Tarozzo、Tiziano Bandiera、Daniele Piomelli、Andrea Cavalli、Giovanni Bottegoni

  DOI：10.1039/c4cc00967c

  日期：——

  The first set of rationally conceived dual dopamine D3 receptor (DRD3) and fatty acid amide hydrolase (FAAH) modulators is presented.

  第一套合理构思的双重多巴胺D3受体（DRD3）和脂肪酸酰胺水解酶（FAAH）调节剂被提出。