2-bromo-N-(3-nitrophenyl)benzamide | 316139-21-6

• 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: 2-bromo-N-(3-nitrophenyl)benzamide
• 英文别名: Benzamide, N-(3-nitrophenyl)-2-bromo-
• CAS: 316139-21-6
• 化学式: C₁₃H₉BrN₂O₃
• 分子量: 321.13
• InChiKey: SMAIGFKAVOUSHO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 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：
  74.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-bromo-N-(3-nitrophenyl)benzamide 在 sodium dithionite 、 三乙酰氧基硼氢化钠 作用下， 以 四氢呋喃 、 水 、 1,2-二氯乙烷 为溶剂， 反应 22.0h， 生成 2-bromo-N-(3-(butylamino)phenyl)benzamide hydrochloride
  参考文献：
  名称：

  Compounds and methods for treating diseases mediated by protease activated receptors

  摘要：

  该发明涉及使用式I的化合物治疗蛋白酶激活受体介导的疾病，通过给予式I的化合物或其前药或代谢物进行治疗。

  公开号：

  US09422262B2
• 作为产物：
  描述：

  2-溴苯甲酸 在 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.5h， 生成 2-bromo-N-(3-nitrophenyl)benzamide
  参考文献：
  名称：

  基于 Na2Te 的发散化学计量的无碱铜辅助合成 C2 对称螺环碲烷和联芳基化合物

  摘要：

  已经开发了一种一锅法 Cu( I ) 辅助合成方法，用于通过使用碲双阴离子从 2-溴-N-芳基苯甲酰胺、苯甲醇和苯甲酸制备具有生物学重要意义的C 2 -对称螺二氮杂、苯甲氧基和苯甲氧基碲烷。 (Te 2- ) 在无碱条件下。此外，在相同的反应条件下，通过使用过量的 Na 2 Te 制备了 C-C 偶联联芳基 1,1'-二酰胺。合成的螺二氮杂碲烷可作为还原 H 2 O 2和硝基-迈克尔反应的有效催化剂。

  DOI：

  10.1039/d2cc02181a

文献信息

• [EN] HETEROCYCLIC LIGANDS OF PAR1 AND METHODS OF USE<br/>[FR] LIGANDS HÉTÉROCYCLIQUES DE PAR1 ET PROCÉDÉS D'UTILISATION
  申请人：UNIV MARQUETTE

  公开号：WO2020172609A1

  公开（公告）日：2020-08-27

  The present invention provides novel compounds with increased plasma stability that modulate PAR1 signaling, and methods of using them. The present invention provides methods of using the novel PAR1 modulators for the treatment of a number of disorders, including, inflammation, thrombosis, kidney disease, sepsis, stroke, as well as proliferation- related diseases. Furthermore, the PAR1 modulators of the present invention provide cytoprotection for certain cells and tissues, for example, in coronary blood vessels and tissues after a heart attack.

  本发明提供了一种具有增加血浆稳定性的新化合物，可以调节PAR1信号传导，并提供了使用它们的方法。本发明提供了使用新型PAR1调节剂治疗多种疾病的方法，包括炎症、血栓形成、肾脏疾病、败血症、中风，以及增殖相关疾病。此外，本发明的PAR1调节剂为某些细胞和组织提供细胞保护作用，例如在心脏病发作后的冠状动脉和组织中。
• An efficient synthesis of biaryl diamides via Ullmann coupling reaction catalyzed by CuI in the presence of Cs2CO3 and TBAB
  作者：Fang Dong、Jian-Quan Liu、Xiang-Shan Wang

  DOI：10.1007/s11164-018-3422-0

  日期：2018.9

  Abstract CuI accompanyied by Cs2CO3 and TBAB was confirmed to be an efficient catalyst combination to promote an Ullmann coupling reaction. It facilitated 2-bromobenzamides to undergo a coupling reaction for the synthesis of symmetrical biaryldiamides in moderate yields at 120 °C under Pd-free conditions. Graphical Abstract

  摘要 Cs 2 CO 3和TBAB伴随的CuI被证实是促进Ullmann偶联反应的有效催化剂组合。它促进了2-溴苯甲酰胺在无钯条件下于120°C进行偶联反应，以中等收率合成对称的联芳基二酰胺。 图形概要
• COMPOUNDS AND METHODS FOR TREATING DISEASES MEDIATED BY PROTEASE ACTIVATED RECEPTORS
  申请人：Dockendorff Chris

  公开号：US20130331411A1

  公开（公告）日：2013-12-12

  The invention relates to the use of a compound of Formula I for the treatment of protease-activated receptor mediated diseases by the administration of a compound of Formula I or a prodrug or metabolite thereof.

  本发明涉及使用式I化合物治疗蛋白酶激活受体介导疾病的方法，该方法通过给予式I化合物或其前药或代谢物来实现。
• Heterocyclic ligands of PAR1 and methods of use
  申请人：Marquette University

  公开号：US11130743B2

  公开（公告）日：2021-09-28

  The present invention provides novel compounds with increased plasma stability that modulate PAR1 signaling, and methods of using them. The present invention provides methods of using the novel PAR1 modulators for the treatment of a number of disorders, including, inflammation, thrombosis, kidney disease, sepsis, stroke, as well as proliferation-related diseases. Furthermore, the PAR1 modulators of the present invention provide cytoprotection for certain cells and tissues, for example, in coronary blood vessels and tissues after a heart attack.

  本发明提供了可调节 PAR1 信号传导的血浆稳定性增强的新型化合物及其使用方法。本发明提供了使用新型 PAR1 调节剂治疗多种疾病的方法，包括炎症、血栓形成、肾病、败血症、中风以及增殖相关疾病。此外，本发明的 PAR1 调节剂还能为某些细胞和组织提供细胞保护，例如心脏病发作后冠状血管和组织的细胞保护。
• Characterization of Protease-Activated Receptor (PAR) ligands: Parmodulins are reversible allosteric inhibitors of PAR1-driven calcium mobilization in endothelial cells
  作者：Disha M. Gandhi、Mark W. Majewski、Ricardo Rosas、Kaitlin Kentala、Trevor J. Foster、Eric Greve、Chris Dockendorff

  DOI：10.1016/j.bmc.2018.04.016

  日期：2018.5

  Several classes of ligands for Protease-Activated Receptors (PARs) have shown impressive anti-inflammatory and cytoprotective activities, including PAR2 antagonists and the PAR1-targeting parmodulins. In order to support medicinal chemistry studies with hundreds of compounds and to perform detailed mode-of-action studies, it became important to develop a reliable PAR assay that is operational with endothelial cells, which mediate the cytoprotective effects of interest. We report a detailed protocol for an intracellular calcium mobilization assay with adherent endothelial cells in multiwell plates that was used to study a number of known and new PAR1 and PAR2 ligands, including an alkynylated version of the PAR1 antagonist RWJ-58259 that is suitable for the preparation of tagged or conjugate compounds. Using the cell line EA. hy926, it was necessary to perform media exchanges with automated liquid handling equipment in order to obtain optimal and reproducible antagonist concentration-response curves. The assay is also suitable for study of PAR2 ligands; a peptide antagonist reported by Fairlie was synthesized and found to inhibit PAR2 in a manner consistent with reports using epithelial cells. The assay was used to confirm that vorapaxar acts as an irreversible antagonist of PAR1 in endothelium, and parmodulin 2 (ML161) and the related parmodulin RR-90 were found to inhibit PAR1 reversibly, in a manner consistent with negative allosteric modulation. (C) 2018 Elsevier Ltd. All rights reserved.