美澳沧仑 | 2577-72-2

• 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: 美澳沧仑
• 中文别名: 苯溴沙仑；苯洒兰
• 英文名称: 3,5-dibromo-2-hydroxy-N-phenylbenzamide
• 英文别名: Metabromsalan
• CAS: 2577-72-2
• 化学式: C₁₃H₉Br₂NO₂
• 分子量: 371.028
• InChiKey: YALKQBRWLMDVSA-UHFFFAOYSA-N

物化性质

• 熔点：
  137-138 °C
• 沸点：
  369.5±42.0 °C(Predicted)
• 密度：
  1.863±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  18
• 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：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  美澳沧仑 、 氯甲酸乙酯 以 吡啶 为溶剂， 反应 1.0h， 以60%的产率得到6,8-Dibromo-3-phenyl-1,3-benzoxazine-2,4-dione
  参考文献：
  名称：

  抗分枝杆菌物质的化学结构与其对非典型菌株的活性之间的关系。第 14 部分：3-Aryl-6,8-dihalo-2H-1,3-benzoxazine-2,4 (3H) -diones

  摘要：

  6,8-二氯-3-苯基-2H-苯并恶嗪-2,4(3H)-二酮的八种衍生物和6,8-二溴-3-苯基-2H-1,3-苯并恶嗪-的九种衍生物苯环上取代的 2,4 (3H)-二酮是通过相应的水杨酰苯胺与氯甲酸乙酯反应制备的。在体外评估了这些化合物对结核分枝杆菌、堪萨斯分枝杆菌和鸟分枝杆菌的抗分枝杆菌活性。它们的活性随着苯环上取代基的疏水性和吸电子能力的增加而增加。

  DOI：

  10.1002/(sici)1521-4184(199801)331:1<3::aid-ardp3>3.0.co;2-2
• 作为产物：
  描述：

  3,5-Dibromo-2-methoxybenzoyl chloride 在 吡啶 、 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 90.0h， 生成 美澳沧仑
  参考文献：
  名称：

  Hydroxybiphenylamide GroEL/ES Inhibitors Are Potent Antibacterials against Planktonic and Biofilm Forms of Staphylococcus aureus

  摘要：

  We recently reported the identification of a GroEL/ES inhibitor (1, N-(4-(benzo[d]thiazol-2-ylthio)-3-chlorophenyl)-3,5-dibromo-2-hydroxybenzamide) that exhibited in vitro antibacterial effects against Staphylococcus aureus comparable to vancomycin, an antibiotic of last resort. To follow up, we have synthesized 43 compound 1 analogs to determine the most effective functional groups of the scaffold for inhibiting GroEL/ES and killing bacteria. Our results identified that the benzothiazole and hydroxyl groups are important for inhibiting GroEL/ES-mediated folding functions, with the hydroxyl essential for antibacterial effects. Several analogs exhibited >50-fold selectivity indices between antibacterial efficacy and cytotoxicity to human liver and kidney cells in cell culture. We found that MRSA was not able to easily generate acute resistance to lead inhibitors in a gain-of-resistance assay and that lead inhibitors were able to permeate through established S. aureus biofilms and maintain their bactericidal effects.

  DOI：

  10.1021/acs.jmedchem.8b01293

文献信息

• [EN] CARBONATE PRODRUGS AND METHODS OF USING THE SAME<br/>[FR] PROMÉDICAMENTS CARBONATÉS ET LEURS MÉTHODES D'UTILISATION
  申请人：NEUROGESX INC

  公开号：WO2009143297A1

  公开（公告）日：2009-11-26

  The present invention provides carbonate prodrugs which comprise a carbonic phosphoric anhydride prodrug moiety attached to the hydroxyl or carboxyl group of a parent drug moiety. The prodrugs may provide improved physicochemical properties over the parent drug. Also provided are methods of treating a disease or condition that is responsive to the parent drug using the carbonate prodrugs, as well as kits and unit dosages.

  本发明提供了碳酸盐前药，其包括连接到母药基团的羟基或羧基上的碳酸磷酸酐前药基团。这些前药可能比母药具有改进的物理化学性质。还提供了使用碳酸盐前药治疗对母药具有响应的疾病或症状的方法，以及配套工具和单剂量。
• 5-Bromo- and 3,5-dibromo-2-hydroxy-N-phenylbenzamides — inhibitors of photosynthesis
  作者：Katarína Kráľová、František Šeršeň、Matúš Peško、Karel Waisser、Lenka Kubicová

  DOI：10.2478/s11696-013-0416-7

  日期：2014.1.1

  5-Bromo-(Br-PBA) and 3,5-dibromo-2-hydroxy-N-phenylbenzamides (Br2-PBA) inhibited photosynthetic electron transport (PET) and their inhibitory efficiency depended on the compound lipophilicity as well as on the electronic properties of the R substituent in the N-phenyl moiety. Br-PBA showed higher PET inhibiting activity than Br2-PBA with the same R substituent. The most effective inhibitors in the tested series were the derivatives with R = 3-F (Br-PBA; IC50 = 4.3 μmol dm−3) and R = 3-Cl (Br2-PBA; IC50 = 8.6 μmol dm−3). Bilinear dependence of the PET inhibiting activity on the lipophilicity of the compounds as well as on the Hammett constant, σ, of the R substituent was observed for both investigated series. Using EPR spectroscopy it was found that the site of action of the tested compounds in the photosynthetic apparatus is situated on the donor side of PS 2, in D· or in the Z·/D· intermediates. Interaction of the studied compounds with chlorophyll a and aromatic amino acids present in the pigment-protein complexes mainly in photosystem 2 was documented by fluorescence spectroscopy.

  摘要：5-溴-(Br-PBA)和3,5-二溴-2-羟基-N-苯基苯甲酰胺（Br2-PBA）抑制了光合作用电子传递（PET），它们的抑制效率取决于化合物的亲脂性以及N-苯基基团中R取代基的电子性质。Br-PBA表现出比具有相同R取代基的Br2-PBA更高的PET抑制活性。在测试系列中，具有R = 3-F（Br-PBA; IC50 = 4.3 μmol dm−3）和R = 3-Cl（Br2-PBA; IC50 = 8.6 μmol dm−3）的衍生物是最有效的抑制剂。对于两个研究系列，观察到了PET抑制活性与化合物的亲脂性以及R取代基的Hammett常数σ之间的双线性依赖关系。使用EPR光谱学发现，测试化合物在光合作用器官中的作用位点位于PS 2的给体侧，在D·或在Z·/D·中间体中。通过荧光光谱学证明了研究化合物与叶绿素a和存在于色素蛋白复合物中的芳香氨基酸的相互作用主要发生在光系统2中。
• [EN] COMPOUNDS AND METHODS OF INHIBITING BACTERIAL CHAPERONIN SYSTEMS<br/>[FR] COMPOSÉS ET MÉTHODES D'INHIBITION DE SYSTÈMES DE CHAPERONINE BACTÉRIENNE
  申请人：UNIV INDIANA TRUSTEES

  公开号：WO2020092947A1

  公开（公告）日：2020-05-07

  The present disclosure relates to novel compounds and methods of killing or inhibiting the growth of bacteria. In some embodiments, a method of killing or inhibiting the growth of bacteria is provided. The method comprises administering a compound of formula I or a pharmaceutically acceptable salt thereof to bacteria. In some embodiments, a method of killing or inhibiting the growth of bacteria is provided. The method comprises administering an anthelmintic to bacteria.

  本公开涉及新化合物和杀灭或抑制细菌生长的方法。在某些实施方式中，提供了一种杀灭或抑制细菌生长的方法。该方法包括向细菌施用式I的化合物或其药学上可接受的盐。在某些实施方式中，提供了一种杀灭或抑制细菌生长的方法。该方法包括向细菌施用驱虫药。
• Diagnostic/therapeutic agents
  申请人：Klaveness Jo

  公开号：US20050002865A1

  公开（公告）日：2005-01-06

  Targetable diagnostic and/or therapeutically active agents, e.g. ultrasound contrast agents, comprising a suspension in an aqueous carrier liquid of a reporter comprising gas-containing or gas-generating material, said agent being capable of forming at least two types of binding pairs with a target.

  可定位的诊断和/或治疗活性剂，例如超声对比剂，包括悬浮在水载体液中的报告物，该报告物包含含气体或生成气体的材料，该剂能够与目标形成至少两种结合对。
• CARBONATE PRODRUGS AND METHODS OF USING THE SAME
  申请人：Muhammad Naweed

  公开号：US20110212927A1

  公开（公告）日：2011-09-01

  The present invention provides carbonate prodrugs which comprise a carbonic phosphoric anhydride prodrug moiety attached to the hydroxyl or carboxyl group of a parent drug moiety. The prodrugs may provide improved physicochemical properties over the parent drug. Also provided are methods of treating a disease or condition that is responsive to the parent drug using the carbonate prodrugs, as well as kits and unit dosages.

  本发明提供了碳酸盐前药，其包括一个碳酸磷酸酐前药基团，附着在母药基团的羟基或羧基上。这些前药可能比母药具有更好的物理化学性质。还提供了使用碳酸盐前药治疗对母药有反应的疾病或病症的方法，以及工具包和单元剂量。