N-(4-溴苯基)-5-氯-2-羟基苯甲酰胺 | 2627-75-0

• 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: N-(4-溴苯基)-5-氯-2-羟基苯甲酰胺
• 英文名称: N-(4-bromophenyl)-5-chloro-2-hydroxyl benzamide
• 英文别名: N-(4-bromophenyl)-5-chloro-2-hydroxybenzamide；5-chloro-N-(4'-bromophenyl)-2-hydroxybenzamide
• CAS: 2627-75-0
• 化学式: C₁₃H₉BrClNO₂
• 分子量: 326.577
• InChiKey: RLACRPKMRNEAIU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 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

反应信息

• 作为反应物：
  描述：

  N-(4-溴苯基)-5-氯-2-羟基苯甲酰胺 在 盐酸 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 生成
  参考文献：
  名称：

  New derivatives of salicylamides: Preparation and antimicrobial activity against various bacterial species

  摘要：

  Three series of salicylanilides, esters of N-phenylsalicylamides and 2-hydroxy-N-[1-(2-hydroxyphenylamino)-1-oxoalkan-2-yl]benzamides, in total thirty target compounds were synthesized and characterized. The compounds were evaluated against seven bacterial and three mycobacterial strains. The antimicrobial activities of some compounds were comparable or higher than the standards ampicillin, ciprofloxacin or isoniazid. Derivatives 3f demonstrated high biological activity against Staphylococcus aureus (<= 0.03 mu mol/L), Mycobacterium marinum (<= 0.40 mu mol/L) and Mycobacterium kansasii (1.58 mu mol/L), 3g shows activity against Clostridium perfringens (<= 0.03 mu mol/L) and Bacillus cereus (0.09 mu mol/L), 3h against Pasteurella multocida (<= 0.03 mu mol/L) and M. kansasii (<= 0.43 mu mol/L), 3i against methicillin-resistant S. aureus and B. cereus (<= 0.03 mu mol/L). The structure-activity relationships are discussed for all the compounds. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.08.029
• 作为产物：
  描述：

  5-氯水杨酰苯胺 在 溴 作用下， 生成 N-(4-溴苯基)-5-氯-2-羟基苯甲酰胺
  参考文献：
  名称：

  DE920790

  摘要：

  公开号：

文献信息

• 2-Hydroxy-N-phenylbenzamides and Their Esters Inhibit Acetylcholinesterase and Butyrylcholinesterase
  作者：Martin Krátký、Šárka Štěpánková、Neto-Honorius Houngbedji、Rudolf Vosátka、Katarína Vorčáková、Jarmila Vinšová

  DOI：10.3390/biom9110698

  日期：——

  The development of novel inhibitors of acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) represents a viable approach to alleviate Alzheimer's disease. Thirty-six halogenated 2-hydroxy-N-phenylbenzamides (salicylanilides) with various substitution patterns and their esters with phosphorus-based acids were synthesized in yields of 72% to 92% and characterized. They were evaluated for in

  新型乙酰胆碱酯酶（AChE）和丁酰胆碱酯酶（BuChE）抑制剂的开发代表了减轻阿尔茨海默氏病的可行方法。合成了36种具有各种取代方式的卤代2-羟基-N-苯基苯甲酰胺（水杨酰苯胺）及其与磷基酸的酯，收率72％至92％，并进行了表征。使用改良的Ellman分光光度法评估了它们对电鳗AChE和马血清BuChE的体外抑制作用。苯甲酰胺在33.1至85.8 µM的窄浓度范围内表现出对AChE的中等抑制作用，IC50值较高。BuChE的IC50值较高（53.5-228.4 µM）。大多数衍生物比BuChE更有效地抑制AChE，并且与rivastigmine（一种用于治疗阿尔茨海默氏病的成熟胆碱酯酶抑制剂）相当或优于。磷基酯尤其具有5-氯-2-[4-（三氟甲基）苯基]氨基甲酰基}苯基二乙基亚磷酸酯5c优越的BuChE活性（IC50 = 2.4 µM）。该衍生物也是BuChE的最选择性抑制剂。它引起了两
• New antituberculotics originated from salicylanilides with promising in vitro activity against atypical mycobacterial strains
  作者：Aleš Imramovský、Jarmila Vinšová、Juana Monreal Férriz、Rafael Doležal、Josef Jampílek、Jarmila Kaustová、Filip Kunc

  DOI：10.1016/j.bmc.2009.04.008

  日期：2009.5

  better bio-availability and as more efficient transport forms through the mycobacterial cell membranes due to the higher lipophilicity. The experimental and calculated lipophilicity, stability, antituberculotic activity, cytotoxicity as well as the quantitative structure–activity relationships (QSARs) explored by the Intelligent Problem Solver (IPS) in Trajan Neural Network Simulator 6.0 are presented

  制备了一系列新的30种N-保护的氨基酸酯，作为不断寻找新的抗结核活性水杨酰苯胺的一部分。酯具有高抵抗体外活性的结核分枝杆菌，鸟分枝杆菌，以及两种菌株堪萨斯分枝杆菌，其中一个是患者的分离株，所有测试菌株的MIC范围为1–32μmol/ L。所制备的酯可以被认为是具有更高生物利用度的前药，并且由于更高的亲脂性被认为是更有效的通过分枝杆菌细胞膜的转运形式。介绍了通过Trajan神经网络模拟器6.0中的智能问题解决器（IPS）探索的实验和计算的亲脂性，稳定性，抗结核活性，细胞毒性以及定量构效关系（QSAR）。
• Salicylanilide esterification: unexpected formation of novel seven-membered rings
  作者：Aleš Imramovský、Jarmila Vinšová、Juana Monreal Férriz、Jiřı´ Kuneš、Milan Pour、Martin Doležal

  DOI：10.1016/j.tetlet.2006.05.110

  日期：2006.7

  Novel benzoxazepines were prepared upon esterification of biologically active salicylanilides with some N-protected amino acids. While the desired conjugates of the salicylanilides with the amino acids were obtained when sterically more demanding amino acids were used, benzoxazepines were formed as a result of a seven-exo-trig cyclization in the case of N-protected glycine and alanine. The structures

  通过将具有生物活性的水杨酰苯胺与一些N保护的氨基酸酯化来制备新型苯并氮杂pine。当使用空间上要求更高的氨基酸时，虽然获得了水杨酰苯胺与氨基酸的所需共轭物，但在N-保护的甘氨酸和丙氨酸的情况下，由于七-外-trig环化作用而形成了苯并氮杂pine。产物的结构通过2D NMR方法确认，无环共轭物的进一步转化为提出的环化机理提供了额外的支持。
• Investigating Spectrum of Biological Activity of 4- and 5-Chloro-2-hydroxy-N-[2-(arylamino)-1-alkyl-2-oxoethyl]benzamides
  作者：Ales Imramovsky、Matus Pesko、Katarina Kralova、Marcela Vejsova、Jirina Stolarikova、Jarmila Vinsova、Josef Jampilek

  DOI：10.3390/molecules16032414

  日期：——

  In this study, a series of twenty-two 5-chloro-2-hydroxy-N-[2-(arylamino)-1-alkyl-2-oxoethyl]benzamides and ten 4-chloro-2-hydroxy-N-[2-(arylamino)-1-alkyl-2-oxoethyl]benzamides is described. The compounds were analyzed using RP-HPLC to determine lipophilicity. Primary in vitro screening of the synthesized compounds was performed against mycobacterial, bacterial and fungal strains. They were also evaluated for their activity related to the inhibition of photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts. The compounds showed biological activity comparable with or higher than the standards isoniazid, fluconazole, penicillin G or ciprofloxacin. For all the compounds, the relationships between the lipophilicity and the chemical structure of the studied compounds as well as their structure-activity relationships are discussed.

  在本研究中，描述了一系列二十二种5-氯-2-羟基-N-[2-(芳胺基)-1-烷基-2-氧乙基]苯甲酰胺和十种4-氯-2-羟基-N-[2-(芳胺基)-1-烷基-2-氧乙基]苯甲酰胺。使用RP-HPLC分析这些化合物以确定其亲脂性。对合成的化合物进行了针对分枝杆菌、细菌和真菌株的初步体外筛选。还评估了它们对菠菜（Spinacia oleracea L.）叶绿体中光合电子传递（PET）的抑制活性。这些化合物的生物活性与标准药物异烟肼、氟康唑、青霉素G或环丙沙星相当或更高。对于所有化合物，讨论了其亲脂性与化学结构之间的关系以及其构效关系。
• Novel salicylanilides from 4,5-dihalogenated salicylic acids: Synthesis, antimicrobial activity and cytotoxicity
  作者：Georgios Paraskevopoulos、Sara Monteiro、Rudolf Vosátka、Martin Krátký、Lucie Navrátilová、František Trejtnar、Jiřina Stolaříková、Jarmila Vinšová

  DOI：10.1016/j.bmc.2017.01.016

  日期：2017.2

  Salicylanilides have proved their activity against tuberculosis (TB). One weak electron-withdrawing substituent is favored at the salicylic part, specially Cl or Br atoms at positions 4 or 5. On the other hand, the antimycobacterial activity of salicylanilides is negatively affected when a strong electron-withdrawing substituent (NO2) is present at the same positions. Herein we describe the synthesis

  水杨酰苯胺已证明具有抗结核病（TB）的活性。水杨酸部分优选一个弱吸电子取代基，特别是4或5位的Cl或Br原子。另一方面，当强吸电子取代基（NO 2）出现在相同位置。本文中，我们描述了在水杨酸部分具有两个弱吸电子基团（卤素原子）的新型水杨酰苯胺的合成与表征，并将其抗结核活性与其单卤代类似物进行了比较。事实证明，所有二卤代衍生物在非常窄的微摩尔范围内（MIC = 1-4μM）都具有抗结核活性，与它们的活性最高的单卤代类似物相似。更重要的是，对最具活性的最终分子进行了进一步筛选，以抵抗多药耐药菌株，发现它们的生长抑制在0.5–4μM的范围内。