3-(3,4-dichlorobenzyl)benzaldehyde | 1459215-78-1

• 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: 3-(3,4-dichlorobenzyl)benzaldehyde
• 英文别名: 3-[(3,4-Dichlorophenyl)methyl]benzaldehyde
• CAS: 1459215-78-1
• 化学式: C₁₄H₁₀Cl₂O
• 分子量: 265.139
• InChiKey: NCAWEBFONMQMRF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-(3,4-dichlorobenzyl)benzaldehyde 、 丙二腈 在 L-脯氨酸 作用下， 以 乙醇 为溶剂， 以90%的产率得到2-(3-(3,4-dichlorobenzyl)benzylidene)malononitrile
  参考文献：
  名称：

  [EN] POTENTIATORS OF BETA-LACTAM ANTIBIOTICS AND COMBINATION THERAPY
  [FR] POTENTIALISATEURS D'ANTIBIOTIQUES DE TYPE BÊTA-LACTAMES ET POLYTHÉRAPIE

  摘要：

  耐甲氧西林金黄色葡萄球菌（MRSA）的蛋白质是一种抗生素感应器/信号传导体，在暴露于β-内酰胺类抗生素时会发生磷酸化。这一事件对于引发生物化学事件的开始至关重要，从而诱导抗生素抗性。在本文所述的抑制剂存在的情况下，磷酸化和抗生素抗性表型可以被废除，从而恢复该生物对β-内酰胺类抗生素的敏感性。因此，该发明提供了化合物和方法，用于废除对β-内酰胺类抗生素的抗性，并通过增强β-内酰胺类抗生素来治疗由易于产生抗性的抗生素引起的感染。

  公开号：

  WO2017106552A1
• 作为产物：
  描述：

  3-甲酰基苯硼酸 、 3,4-二氯苄溴 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 以68%的产率得到3-(3,4-dichlorobenzyl)benzaldehyde
  参考文献：
  名称：

  [EN] POTENTIATORS OF BETA-LACTAM ANTIBIOTICS AND COMBINATION THERAPY
  [FR] POTENTIALISATEURS D'ANTIBIOTIQUES DE TYPE BÊTA-LACTAMES ET POLYTHÉRAPIE

  摘要：

  耐甲氧西林金黄色葡萄球菌（MRSA）的蛋白质是一种抗生素感应器/信号传导体，在暴露于β-内酰胺类抗生素时会发生磷酸化。这一事件对于引发生物化学事件的开始至关重要，从而诱导抗生素抗性。在本文所述的抑制剂存在的情况下，磷酸化和抗生素抗性表型可以被废除，从而恢复该生物对β-内酰胺类抗生素的敏感性。因此，该发明提供了化合物和方法，用于废除对β-内酰胺类抗生素的抗性，并通过增强β-内酰胺类抗生素来治疗由易于产生抗性的抗生素引起的感染。

  公开号：

  WO2017106552A1

文献信息

• The synthesis and SAR study of phenylalanine-derived (Z)-5-arylmethylidene rhodanines as anti-methicillin-resistant Staphylococcus aureus (MRSA) compounds
  作者：Bhargav A. Patel、Charles R. Ashby、Diane Hardej、Tanaji T. Talele

  DOI：10.1016/j.bmcl.2013.08.059

  日期：2013.10

  A focused library of rhodanine compounds containing novel substituents at the C5-position was synthesized and tested in vitro against a panel of clinically relevant MRSA strains. The present SAR study was based on our lead compound 1 (MIC = 1.95 mu g/mL), with a focus on identifying optimal C5-arylidene substituents. In order to obtain this objective, we condensed several unique aromatic aldehydes with phenylalanine-derived rhodanine intermediates to obtain C5-substituted target rhodanine compounds for evaluation as anti-MRSA compounds. These efforts produced three compounds with significant efficacy: 23, 32 and 44, with MIC values ranging from 0.98 to 1.95 mu g/mL against all tested MRSA strains as compared to the reference antibiotics penicillin G (MIC = 15.60-250.0 mu g/mL) and ciprofloxacin (MIC = 7.80-62.50 mu g/mL) and comparable to that of vancomycin (MIC = 0.48 mu g/mL). In addition, compounds 24, 28, 37, 41, 46 and 48 (MIC = 1.95-3.90 mu g/mL) were efficacious against all MRSA strains. The majority of the synthesized compounds had bactericidal activity at concentrations only two to fourfold higher than their MIC. Overall, the results suggest that compounds 23, 32 and 44 may be of potential use in the treatment of MRSA infections. (C) 2013 Elsevier Ltd. All rights reserved.
• Cinnamonitrile Adjuvants Restore Susceptibility to β-Lactams against Methicillin-Resistant <i>Staphylococcus aureus</i>
  作者：Enrico Speri、Choon Kim、Stefania De Benedetti、Yuanyuan Qian、Elena Lastochkin、Jennifer Fishovitz、Jed F. Fisher、Shahriar Mobashery

  DOI：10.1021/acsmedchemlett.9b00169

  日期：2019.8.8

  beta-Lactams are used routinely to treat Staphylococcus aureus infections. However, the emergence of methicillin-resistant S. aureus (MRSA) renders them clinically precarious. We describe a class of cinnamonitrile adjuvants that restore the activity of oxacillin (a penicillin member of the beta-lactams) against MRSA. The lead adjuvants were tested against six important strains of MRSA, one vancomycin-intermediate S. aureus (VISA) strain, and one linezolid-resistant S. aureus strain. Five compounds out of 84 total compounds showed broad potentiation. At 8 mu M (E)-3-(5-(3,4-dichlorobenzy1)-2-(trifluoromethoxy)phenyl)-2-(methylsulfonyl)acrylonitrile (26) potentiated oxacillin with a >4000-fold reduction of its MIC (from 256 to 0.06 mg.L-1). This class of adjuvants holds promise for reversal of the resistance phenotype of MRSA.