1,3‐bis[4‐fluoro‐3‐(trifluoromethyl)phenyl]urea | 35685-20-2

• 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: 1,3‐bis[4‐fluoro‐3‐(trifluoromethyl)phenyl]urea
• 英文别名: 1,3-Bis[4-fluoro-3-(trifluoromethyl)phenyl]urea
• CAS: 35685-20-2
• 化学式: C₁₅H₈F₈N₂O
• 分子量: 384.229
• InChiKey: AVLRRXROFDOKHR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  41.1
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  2-氟-5-硝基三氟甲苯 在 铁粉 、 sodium carbonate 、 氯化铵 作用下， 生成 1,3‐bis[4‐fluoro‐3‐(trifluoromethyl)phenyl]urea
  参考文献：
  名称：

  芳族氟化合物。十二。N-（氟苯基）氨基甲酸酯。

  摘要：

  DOI：

  10.1021/jm00334a041

文献信息

• Progress in antischistosomal N,N′-diaryl urea SAR
  作者：Jianbo Wu、Chunkai Wang、Derek Leas、Mireille Vargas、Karen L. White、David M. Shackleford、Gong Chen、Austin G. Sanford、Ryan M. Hemsley、Paul H. Davis、Yuxiang Dong、Susan A. Charman、Jennifer Keiser、Jonathan L. Vennerstrom

  DOI：10.1016/j.bmcl.2017.12.064

  日期：2018.2

  solubility, but also to maximize structural diversity. Replacement of one of the 4-fluoro-3-trifluoromethylphenyl substructures of lead N,N′-diaryl urea 1 with azaheterocycles and benzoic acids, benzamides, or benzonitriles decreased lipophilicity, and in most cases, increased aqueous solubility. There was no clear relationship between lipophilicity and metabolic stability, although all compounds with

  N，N′-二芳基尿素最近已经出现为新的抗血吸虫化学型。现在，我们描述了针对曼氏血吸虫的二十种新的N，N'-二芳基尿素的理化概况分析，体外ADME，血浆暴露以及离体和体内活性，这些N，N'-二芳基尿素主要设计用于增加水溶性，同时也可以最大程度地提高结构多样性。N，N'-二芳基尿素1铅的4-氟-3-三氟甲基苯基亚结构之一的取代与氮杂杂环和苯甲酸，苯甲酰胺或苄腈一起使用会降低亲脂性，并且在大多数情况下会增加水溶性。亲脂性与代谢稳定性之间没有明确的关系，尽管所有具有3-三氟甲基-4-吡啶基亚结构的化合物在代谢上都是稳定的。含有4-氟-3-三氟甲基苯基，3-三氟甲基-4-吡啶基，2，2-二氟苯并二恶唑或4-苄腈亚结构的N，N′-二芳基脲对离体曼氏梭菌具有高活性，并且细胞毒性相对较低。ñ，ñ具有3-三氟甲基-4-吡啶基和2,2-二氟苯并二恶唑亚结构的-二芳基尿素具有最高的暴露量，而具有4-氟-3-三氟
• Discovery of N,N'‐diarylurea molecules with activity against multidrug‐resistant Staphylococcus aureus
  作者：Hui‐Hui Yeo、Yu‐Hsuan Jao、Fan‐Wei Yang、Min‐Hsuan Kuo、Meng‐Hsuan Lee、Chung‐Wei Shiau、Hao‐Chieh Chiu、Jung‐Chen Su

  DOI：10.1002/ardp.202400047

  日期：2024.8

  The emergence and global spread of methicillin‐resistant Staphylococcus aureus (MRSA) pose a serious threat to public health, underscoring the urgent need for novel antibacterial interventions. Here, we screened 18 newly synthesized N,N’‐diarylurea derivatives to identify compounds with activity against MRSA. Our investigations led to the discovery of a small molecule, SCB‐24, which exhibited promising antimicrobial activity against MRSA USA300. Notably, SCB‐24 demonstrated high activity even in the presence of 10% fetal bovine serum and showed excellent selectivity for bacterial over mammalian cells. SCB‐24 also showed potent activity against various MRSA strains, including those resistant to second‐ and third‐line antibiotics. Importantly, the efficacy of SCB‐24 was inferior to that of vancomycin in MRSA‐infected Galleria mellonella larvae. Overall, our findings suggest that SCB‐24 has great potential as a new therapeutic for multidrug‐resistant S. aureus infections.