2-(4-chlorophenoxy)-5-fluoro-benzaldehyde | 289717-78-8

• 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: 2-(4-chlorophenoxy)-5-fluoro-benzaldehyde
• 英文别名: 2-(4-Chlorophenoxy)-5-fluorobenzaldehyde
• CAS: 289717-78-8
• 化学式: C₁₃H₈ClFO₂
• mdl: MFCD11639911
• 分子量: 250.657
• InChiKey: RYYUVUCBSIGEIF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-chlorophenoxy)-5-fluoro-benzaldehyde 、 3-amino-4-butylaminobenzonitrile 在 sodium metabisulfite 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以50.5%的产率得到1-butyl-2-[2-(4-chlorophenoxy)-5-fluorophenyl]-1H-benzimidazole-5-carbonitrile
  参考文献：
  名称：

  Synthesis andIn VitroActivity of Polyhalogenated 2-phenylbenzimidazoles as a New Class of anti-MRSA and Anti-VRE Agents

  摘要：

  A series of novel polyhalogenated 2‐phenylbenzimidazoles have been synthesized and evaluated for in vitro antistaphylococcal activity against drug‐resistant bacterial strains (methicillin‐resistant Staphylococcus aureus, and vancomycin‐resistant Enterococcus faecium. Certain compounds inhibit bacterial growth perfectly. 11 was active than vancomycin (0.78 μg/mL) with the lowest MIC values with 0.19 μg/mL against methicillin‐resistant Staphylococcus aureus, 8 and 35 exhibited best inhibitory activity against vancomycin‐resistant Enterococcus faecium (1.56 μg/mL). The mechanism of action for this class of compounds appears to be different than clinically used antibiotics. These polyhalogenated benzimidazoles have potential for further investigation as a new class of potent anti‐methicillin‐resistant Staphylococcus aureus and anti‐vancomycin‐resistant Enterococcus faecium agents.

  DOI：

  10.1111/cbdd.12623
• 作为产物：
  描述：

  2,5-二氟苯甲醛 、 对氯苯酚 在 potassium carbonate 作用下， 以 异丁酰胺 为溶剂， 反应 4.0h， 以44%的产率得到2-(4-chlorophenoxy)-5-fluoro-benzaldehyde
  参考文献：
  名称：

  合成和2'-芳基取代-1抗寄生虫和抗真菌评价ħ，1' ħ - [2,5'] bisbenzimidazolyl -5-甲脒

  摘要：

  一系列2'-芳基取代-1 ħ，1' ħ - [2,5'] - bisbenzimidazolyl -5-甲脒在由4-氨基-3-硝基苄腈开始的6步骤的过程中制备。在体外评价了对布鲁氏锥虫（Tbr），恶性疟原虫（Pf），利什曼原虫多诺尼（Ld）和克鲁氏锥虫（Tc）的抗寄生虫活性以及对白色念珠菌和库氏假丝酵母的抗真菌活性。几种化合物显示出对Tbr和Pf的体外活性与白色念珠菌相比，其对Pf的活性优于氯喹。

  DOI：

  10.1016/j.ejmech.2008.10.003

文献信息

• Synthesis and<i>In Vitro</i>Activity of Polyhalogenated 2-phenylbenzimidazoles as a New Class of anti-MRSA and Anti-VRE Agents
  作者：Hakan Göker、Cigdem Karaaslan、Mustafa Orhan Püsküllü、Sulhiye Yildiz、Yalcin Duydu、Aylin Üstündağ、Can Özgür Yalcin

  DOI：10.1111/cbdd.12623

  日期：2016.1

  A series of novel polyhalogenated 2‐phenylbenzimidazoles have been synthesized and evaluated for in vitro antistaphylococcal activity against drug‐resistant bacterial strains (methicillin‐resistant Staphylococcus aureus, and vancomycin‐resistant Enterococcus faecium. Certain compounds inhibit bacterial growth perfectly. 11 was active than vancomycin (0.78 μg/mL) with the lowest MIC values with 0.19 μg/mL against methicillin‐resistant Staphylococcus aureus, 8 and 35 exhibited best inhibitory activity against vancomycin‐resistant Enterococcus faecium (1.56 μg/mL). The mechanism of action for this class of compounds appears to be different than clinically used antibiotics. These polyhalogenated benzimidazoles have potential for further investigation as a new class of potent anti‐methicillin‐resistant Staphylococcus aureus and anti‐vancomycin‐resistant Enterococcus faecium agents.
• Synthesis and antiparasitic and antifungal evaluation of 2′-arylsubstituted-1H,1′H-[2,5′]bisbenzimidazolyl-5-carboxamidines
  作者：Mehmet Alp、Hakan Göker、Reto Brun、Sulhiye Yıldız

  DOI：10.1016/j.ejmech.2008.10.003

  日期：2009.5

  A series of 2′-arylsubstituted-1H,1′H-[2,5′]-bisbenzimidazolyl-5-carboxamidines were prepared in a six-step process starting from 4-amino-3-nitrobenzonitrile. The antiparasitic activity against Trypanosoma brucei rhodesiense (T.b.r.), Plasmodium falciparum (P.f.), Leishmania donovani (L.d.) and Trypanosoma cruzi (T.c.) and antifungal activity against Candida albicans and Candida krusei were evaluated

  一系列2'-芳基取代-1 ħ，1' ħ - [2,5'] - bisbenzimidazolyl -5-甲脒在由4-氨基-3-硝基苄腈开始的6步骤的过程中制备。在体外评价了对布鲁氏锥虫（Tbr），恶性疟原虫（Pf），利什曼原虫多诺尼（Ld）和克鲁氏锥虫（Tc）的抗寄生虫活性以及对白色念珠菌和库氏假丝酵母的抗真菌活性。几种化合物显示出对Tbr和Pf的体外活性与白色念珠菌相比，其对Pf的活性优于氯喹。