4-chloro-2-(3,4-dichlorophenylcarbamoyl)phenyl 4-(trifluoromethyl)benzoate | 1403607-23-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 缩酚酸和缩酚酸环醚类
• 英文名称: 4-chloro-2-(3,4-dichlorophenylcarbamoyl)phenyl 4-(trifluoromethyl)benzoate
• 英文别名: [4-Chloro-2-[(3,4-dichlorophenyl)carbamoyl]phenyl] 4-(trifluoromethyl)benzoate；[4-chloro-2-[(3,4-dichlorophenyl)carbamoyl]phenyl] 4-(trifluoromethyl)benzoate
• CAS: 1403607-23-7
• 化学式: C₂₁H₁₁Cl₃F₃NO₃
• 分子量: 488.677
• InChiKey: KMQKYZMEGJRHOF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  5-氯代水杨酸 、 3,4-二氯苯胺 在 N,N'-二环己基碳二亚胺 、 三氯化磷 作用下， 以 N,N-二甲基甲酰胺 、 氯苯 为溶剂， 反应 52.33h， 生成 4-chloro-2-(3,4-dichlorophenylcarbamoyl)phenyl 4-(trifluoromethyl)benzoate
  参考文献：
  名称：

  Antifungal Activity of Salicylanilides and Their Esters with 4-(Trifluoromethyl)benzoic Acid

  摘要：

  寻找新型抗菌药物仍然是药物化学领域的热门话题。本研究介绍了十八种水杨酰替苯胺酯及其母体水杨酰替苯胺的合成和分析数据，这些化合物均为4-(三氟甲基)苯甲酸酯类。它们作为潜在的抗真菌剂在体外针对八种真菌菌株进行了抗菌活性测试。所介绍的衍生物的抗真菌活性并不一致，其中霉菌的最低抑制浓度（MIC）³ 0.49 µmol/L，显示出比酵母（MIC ³ 1.95 µmol/L）更高的敏感性。然而，由于其低溶解性，无法评估一系列4-(三氟甲基)苯甲酸酯。总体而言，活性最强的水杨酰替苯胺是N-(4-溴苯基)-4-氯-2-羟基苯甲酰胺，而在酯类化合物中，相对应的2-(4-溴苯基氨基甲酰基)-5-氯苯基-4-(三氟甲基)苯甲酸酯显示出最低的MIC值，为0.49 µmol/L。然而，通过4-(三氟甲基)苯甲酸酯化水杨酰替苯胺并未明确导致更高的抗真菌效力。

  DOI：

  10.3390/molecules17089426

文献信息

• Antifungal Activity of Salicylanilides and Their Esters with 4-(Trifluoromethyl)benzoic Acid
  作者：Martin Krátký、Jarmila Vinšová

  DOI：10.3390/molecules17089426

  日期：——

  Searching for novel antimicrobial agents still represents a current topic in medicinal chemistry. In this study, the synthesis and analytical data of eighteen salicylanilide esters with 4-(trifluoromethyl)benzoic acid are presented. They were assayed in vitro as potential antimycotic agents against eight fungal strains, along with their parent salicylanilides. The antifungal activity of the presented derivatives was not uniform and moulds showed a higher susceptibility with minimum inhibitory concentrations (MIC) ³ 0.49 µmol/L than yeasts (MIC ³ 1.95 µmol/L). However, it was not possible to evaluate a range of 4-(trifluoromethyl)benzoates due to their low solubility. In general, the most active salicylanilide was N-(4-bromophenyl)-4-chloro-2-hydroxybenzamide and among esters, the corresponding 2-(4-bromophenylcarbamoyl)-5-chlorophenyl 4-(trifluoromethyl) benzoate exhibited the lowest MIC of 0.49 µmol/L. However, the esterification of salicylanilides by 4-(trifluoromethyl)benzoic acid did not result unequivocally in a higher antifungal potency.

  寻找新型抗菌药物仍然是药物化学领域的热门话题。本研究介绍了十八种水杨酰替苯胺酯及其母体水杨酰替苯胺的合成和分析数据，这些化合物均为4-(三氟甲基)苯甲酸酯类。它们作为潜在的抗真菌剂在体外针对八种真菌菌株进行了抗菌活性测试。所介绍的衍生物的抗真菌活性并不一致，其中霉菌的最低抑制浓度（MIC）³ 0.49 µmol/L，显示出比酵母（MIC ³ 1.95 µmol/L）更高的敏感性。然而，由于其低溶解性，无法评估一系列4-(三氟甲基)苯甲酸酯。总体而言，活性最强的水杨酰替苯胺是N-(4-溴苯基)-4-氯-2-羟基苯甲酰胺，而在酯类化合物中，相对应的2-(4-溴苯基氨基甲酰基)-5-氯苯基-4-(三氟甲基)苯甲酸酯显示出最低的MIC值，为0.49 µmol/L。然而，通过4-(三氟甲基)苯甲酸酯化水杨酰替苯胺并未明确导致更高的抗真菌效力。
• Antibacterial Activity of Salicylanilide 4-(Trifluoromethyl)-benzoates
  作者：Martin Krátký、Jarmila Vinšová、Eva Novotná、Jana Mandíková、František Trejtnar、Jiřina Stolaříková

  DOI：10.3390/molecules18043674

  日期：——

  The development of novel antimicrobial agents represents a timely research topic. Eighteen salicylanilide 4-(trifluoromethyl)benzoates were evaluated against Mycobacterium tuberculosis, M. avium and M. kansasii, eight bacterial strains including methicillin-resistant Staphylococcus aureus (MRSA) and for the inhibition of mycobacterial isocitrate lyase. Some compounds were further screened against drug-resistant M. tuberculosis and for their cytotoxicity. Minimum inhibitory concentrations (MICs) for all mycobacterial strains were within 0.5–32 μmol/L, with 4-chloro-2-[4-(trifluoromethyl)phenylcarbamoyl]phenyl 4-(trifluoromethyl)benzoate superiority. Gram-positive bacteria including MRSA were inhibited with MICs ³ 0.49 μmol/L, while Gram-negative ones were much less susceptible. Salicylanilide 4-(trifluoromethyl)benzoates showed significant antibacterial properties, for many strains being comparable to standard drugs (isoniazid, benzylpenicillin) with no cross-resistance. All esters showed mild inhibition of mycobacterial isocitrate lyase and four compounds were comparable to 3-nitropropionic acid without a direct correlation between in vitro MICs and enzyme inhibition.

  新型抗菌剂的开发是一个及时的科研课题。评估了18种水杨酰苯胺4-(三氟甲基)苯甲酸酯对结核分枝杆菌、鸟分枝杆菌和堪萨斯分枝杆菌的抗菌活性,包括8种细菌株如耐甲氧西林金黄色葡萄球菌(MRSA)以及对分枝杆菌异柠檬酸裂解酶的抑制作用。对一些化合物进一步筛选其对耐药性结核分枝杆菌的抗菌活性和细胞毒性。所有分枝杆菌株的最小抑菌浓度(MICs)在0.5–32 μmol/L之间,其中4-氯-2-[4-(三氟甲基)苯基氨基甲酰]苯基 4-(三氟甲基)苯甲酸酯表现最优。包括MRSA在内的革兰氏阳性菌的MICs ≥ 0.49 μmol/L,而革兰氏阴性菌的敏感性较低。水杨酰苯胺4-(三氟甲基)苯甲酸酯显示出显著的抗菌特性,对于许多菌株与标准药物(异烟肼、青霉素)相当,没有交叉耐药性。所有酯类对分枝杆菌异柠檬酸裂解酶显示出轻微抑制作用,其中四种化合物与3-硝基丙酸相当,体外MICs与酶抑制之间没有直接相关性。