N-(pyridin-2-yl)-[1,1'-biphenyl]-2-carboxamide | 257941-41-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(pyridin-2-yl)-[1,1'-biphenyl]-2-carboxamide
• 英文别名: 2-phenyl-N-pyridin-2-ylbenzamide
• CAS: 257941-41-6
• 化学式: C₁₈H₁₄N₂O
• 分子量: 274.322
• InChiKey: KSAQMCXOLJMWAQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-氨基吡啶 、 二氢-3-(异十二碳烯基)呋喃-2,5-二酮 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 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 生成 N-(pyridin-2-yl)-[1,1'-biphenyl]-2-carboxamide
  参考文献：
  名称：

  3D-QSAR and 3D-QSSR models of negative allosteric modulators facilitate the design of a novel selective antagonist of human α4β2 neuronal nicotinic acetylcholine receptors

  摘要：

  Subtype selective molecules for alpha 4 beta 2 neuronal nicotinic acetylcholine receptors (nAChRs) have been sought as novel therapeutics for nicotine cessation. alpha 4 beta 2 nAChRs have been shown to be involved in mediating the addictive properties of nicotine while other subtypes (i.e., alpha 3 beta 4 and alpha 7) are believed to mediate the undesired effects of potential CNS drugs. To obtain selective molecules, it is important to understand the physiochemical features of ligands that affect selectivity and potency on nAChR subtypes. Here we present novel QSAR/QSSR models for negative allosteric modulators of human alpha 4 beta 2 nAChRs and human alpha 3 beta 4 nAChRs. These models support previous homology model and site-directed mutagenesis studies that suggest a novel mechanism of antagonism. Additionally, information from the models presented in this work was used to synthesize novel molecules; which subsequently led to the discovery of a new selective antagonist of human alpha 4 beta 2 nAChRs. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.11.051

文献信息

• Amide inhibitors of microsomal triglyceride transfer protein
  申请人：——

  公开号：US20020156281A1

  公开（公告）日：2002-10-24

  The present invention provides compounds having the Formula I 1 The present invention also provides pharmaceutical compositions comprising a compound of Formula I and methods of treatment of atherosclerosis, obesity, restenosis, coronary heart disease, hyperlipoproteinemia, hypercholesterolemia, and hypertriglyceridemia.

  本发明提供具有化学式I的化合物。本发明还提供包含化合物I的药物组合物，以及治疗动脉粥样硬化、肥胖症、再狭窄、冠心病、高脂蛋白血症、高胆固醇血症和高甘油三酯血症的方法。
• Synthesis of <i>ortho</i>-arylated and alkenylated benzamides by palladium-catalyzed denitrogenative cross-coupling reactions of 1,2,3-benzotriazin-4(3<i>H</i>)-ones with organoboronic acids
  作者：Madasamy Hari Balakrishnan、Madasamy Kanagaraj、Velayudham Sankar、Mahesh Kumar Ravva、Subramaniyan Mannathan

  DOI：10.1039/d1nj03706d

  日期：——

  established by using phenyl boronate ester as the coupling partner. The reaction is believed to proceed via a five-membered aza-palladacyclic intermediate. DFT calculations were studied comparing the reactivity of palladium and nickel complexes in the five-membered aza-metallacycle formation from 1,2,3-benzotriazin-4(3H)-ones. The application of the reaction was successfully demonstrated by converting ortho-alkenylated

  描述了一种有效的钯催化脱氮 Suzuki-Miyaura 型 1,2,3-苯并三嗪-4(3 H )-酮与有机硼酸的交叉偶联。该反应与各种芳基和烯基硼酸相容，以良好至高产率提供邻芳基化和烯基化苯甲酰胺。还成功地使用了杂芳族硼酸。与此同时，通过使用苯基硼酸酯作为偶联伙伴建立了偶联反应。据信该反应通过五元氮杂-钯环中间体进行。研究了 DFT 计算，比较了钯和镍配合物在 1,2,3-苯并三嗪-4(3 H）-那些。通过还原反应将邻-烯基化产物以高产率转化为邻-烷基化产物，成功地证明了该反应的应用。
• 3D-QSAR and 3D-QSSR models of negative allosteric modulators facilitate the design of a novel selective antagonist of human α4β2 neuronal nicotinic acetylcholine receptors
  作者：Brandon J. Henderson、Crina M. Orac、Iwona Maciagiewicz、Stephen C. Bergmeier、Dennis B. McKay

  DOI：10.1016/j.bmcl.2011.11.051

  日期：2012.2

  Subtype selective molecules for alpha 4 beta 2 neuronal nicotinic acetylcholine receptors (nAChRs) have been sought as novel therapeutics for nicotine cessation. alpha 4 beta 2 nAChRs have been shown to be involved in mediating the addictive properties of nicotine while other subtypes (i.e., alpha 3 beta 4 and alpha 7) are believed to mediate the undesired effects of potential CNS drugs. To obtain selective molecules, it is important to understand the physiochemical features of ligands that affect selectivity and potency on nAChR subtypes. Here we present novel QSAR/QSSR models for negative allosteric modulators of human alpha 4 beta 2 nAChRs and human alpha 3 beta 4 nAChRs. These models support previous homology model and site-directed mutagenesis studies that suggest a novel mechanism of antagonism. Additionally, information from the models presented in this work was used to synthesize novel molecules; which subsequently led to the discovery of a new selective antagonist of human alpha 4 beta 2 nAChRs. (C) 2011 Elsevier Ltd. All rights reserved.
• US6780883B2
  申请人：——

  公开号：US6780883B2

  公开（公告）日：2004-08-24
• Pyridyl Benzamides as a Novel Class of Potent Inhibitors for the Kinetoplastid <i>Trypanosoma brucei</i>
  作者：Lori Ferrins、Michelle Gazdik、Raphaël Rahmani、Swapna Varghese、Melissa L. Sykes、Amy J. Jones、Vicky M. Avery、Karen L. White、Eileen Ryan、Susan A. Charman、Marcel Kaiser、Christel A. S. Bergström、Jonathan B. Baell

  DOI：10.1021/jm500191u

  日期：2014.8.14

  A whole-organism screen of approximately 87000 compounds against Trypanosoma brucei brucei identified a number of promising compounds for medicinal chemistry optimization. One of these classes of compounds we termed the pyridyl benzamides. While the initial hit had an IC50 of 12 μM, it was small enough to be attractive for further optimization, and we utilized three parallel approaches to develop the structure-activity relationships. We determined that the physicochemical properties for this class are generally favorable with particular positions identified that appear to block metabolism when substituted and others that modulate solubility. Our most active compound is 79, which has an IC50 of 0.045 μM against the human pathogenic strain Trypanosoma brucei rhodesiense and is more than 4000 times less active against the mammalian L6 cell line.