ethyl 1-amino-6-bromo-3,3-dimethyl-3,4-dihydronaphthalene-2-carboxylate

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: ethyl 1-amino-6-bromo-3,3-dimethyl-3,4-dihydronaphthalene-2-carboxylate
• 英文别名: ethyl 1-amino-6-bromo-3,3-dimethyl-4H-naphthalene-2-carboxylate
• 化学式: C₁₅H₁₈BrNO₂
• 分子量: 324.217
• InChiKey: RZEJYFCMUDMYIH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 1-amino-6-bromo-3,3-dimethyl-3,4-dihydronaphthalene-2-carboxylate 在 bis-triphenylphosphine-palladium(II) chloride 、 四(三苯基膦)钯 、 caesium carbonate 、 溶剂黄146 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 甲苯 、 丁酮 为溶剂， 75.0~90.0 ℃ 、101.33 kPa 条件下， 反应 52.0h， 生成 3-allyl-8-benzoyl-5,5-dimethyl-2-((2-(prop-2-yn-1-yloxy)ethyl)thio)-5,6-dihydrobenzo[h]quinazolin-4(3H)-one
  参考文献：
  名称：

  Development of tag-free photoprobes for studies aimed at identifying the target of novel Group A Streptococcus antivirulence agents

  摘要：

  We previously reported the identification and development of novel inhibitors of streptokinase (SK) expression by Group A Streptococcus (GAS), originating from a high throughput cell-based phenotypic screen. Although phenotypic screening is well-suited to identifying compounds that exert desired biological effects in potentially novel ways, it requires follow-up experiments to determine the macromolecular target(s) of active compounds. We therefore designed and synthesized several classes of chemical probes for target identification studies, guided by previously established structure-activity relationships. The probes were designed to first irreversibly photolabel target proteins in the intact bacteria, followed by cell lysis and click ligation with fluorescent tags to allow for visualization on SDS-PAGE gels. This stepwise, 'tag-free' approach allows for a significant reduction in molecular weight and polar surface area compared to full-length fluorescent or biotinylated probes, potentially enhancing membrane permeability and the maintenance of activity. Of the seven probes produced, the three most biologically active were employed in preliminary target identification trials. Despite the potent activity of these probes, specific labeling events were not conclusively observed due to a considerable degree of nonspecific protein binding. Nevertheless, the successful synthesis of potent biologically active probe molecules will serve as a starting point for initiating more sensitive methods of probe-based target identification. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.01.079
• 作为产物：
  描述：

  3-甲基-2-丁烯酸乙酯 、 4-溴-2-甲基苯腈 在 正丁基锂 、 二异丙胺 、 zinc(I) iodide 作用下， 以 正己烷 、 二乙二醇二甲醚 为溶剂， 反应 3.75h， 以50%的产率得到ethyl 1-amino-6-bromo-3,3-dimethyl-3,4-dihydronaphthalene-2-carboxylate
  参考文献：
  名称：

  Development of tag-free photoprobes for studies aimed at identifying the target of novel Group A Streptococcus antivirulence agents

  摘要：

  We previously reported the identification and development of novel inhibitors of streptokinase (SK) expression by Group A Streptococcus (GAS), originating from a high throughput cell-based phenotypic screen. Although phenotypic screening is well-suited to identifying compounds that exert desired biological effects in potentially novel ways, it requires follow-up experiments to determine the macromolecular target(s) of active compounds. We therefore designed and synthesized several classes of chemical probes for target identification studies, guided by previously established structure-activity relationships. The probes were designed to first irreversibly photolabel target proteins in the intact bacteria, followed by cell lysis and click ligation with fluorescent tags to allow for visualization on SDS-PAGE gels. This stepwise, 'tag-free' approach allows for a significant reduction in molecular weight and polar surface area compared to full-length fluorescent or biotinylated probes, potentially enhancing membrane permeability and the maintenance of activity. Of the seven probes produced, the three most biologically active were employed in preliminary target identification trials. Despite the potent activity of these probes, specific labeling events were not conclusively observed due to a considerable degree of nonspecific protein binding. Nevertheless, the successful synthesis of potent biologically active probe molecules will serve as a starting point for initiating more sensitive methods of probe-based target identification. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.01.079

文献信息

• METHODS AND COMPOSITIONS FOR TREATING BACTERIAL INFECTION
  申请人：THE REGENTS OF THE UNIVERSITY OF MICHIGAN

  公开号：US20150132352A1

  公开（公告）日：2015-05-14

  The present invention relates to chemical compounds, methods for their discovery, and their therapeutic and research use. In particular, the present invention provides compounds as therapeutic agents against bacterial infections (e.g., biofilms).

  本发明涉及化学化合物，它们的发现方法，以及它们的治疗和研究用途。具体而言，本发明提供了作为治疗剂抗击细菌感染（例如生物膜）的化合物。
• Methods and compositions for treating bacterial infection
  申请人：Curators of the University of Missouri

  公开号：US10441588B2

  公开（公告）日：2019-10-15

  The present disclosure relates to chemical compounds, methods for their discovery, and their therapeutic and research use. In particular, the present disclosure provides compounds as therapeutic agents against bacterial infections (e.g., biofilms). The present disclosure also provides topical formulations for use in methods for treating bacterial infections.

  本公开涉及化合物、发现化合物的方法及其治疗和研究用途。特别是，本公开内容提供了作为治疗剂的化合物，用于对抗细菌感染（如生物膜）。本公开还提供了用于治疗细菌感染方法的局部制剂。
• [EN] METHODS AND COMPOSITIONS FOR TREATING BACTERIAL INFECTION<br/>[FR] PROCÉDÉS ET COMPOSITIONS POUR TRAITER UNE INFECTION BACTÉRIENNE
  申请人：UNIV MICHIGAN

  公开号：WO2013166282A3

  公开（公告）日：2014-01-23
• US9504688B2
  申请人：——

  公开号：US9504688B2

  公开（公告）日：2016-11-29
• US9814719B2
  申请人：——

  公开号：US9814719B2

  公开（公告）日：2017-11-14