2-三氟甲基-1H-苯并咪唑-5-碳酰肼 | 1011416-26-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 中文名称: 2-三氟甲基-1H-苯并咪唑-5-碳酰肼
• 英文名称: 2-(trifluoromethyl)-1H-benzimidazole-5-carbohydrazide
• 英文别名: 2-trifluormethyl-1H-benzimidazole-5-carbohydrazide；2-(trifluoromethyl)-3H-benzimidazole-5-carbohydrazide
• CAS: 1011416-26-4
• 化学式: C₉H₇F₃N₄O
• 分子量: 244.176
• InChiKey: DAWOZMREQUDUNO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  83.8
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2'-O-acetyl-4''-O-acylimidazolylclarithromycin 、 2-三氟甲基-1H-苯并咪唑-5-碳酰肼 在 甲醇 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 4''-O-(2-trifluormethyl-1H-benzimidazole-5-carbonyl)hydrazinecarbonylclarithromycin
  参考文献：
  名称：

  Synthesis and antibacterial activity of novel 4″-O-benzimidazolyl clarithromycin derivatives

  摘要：

  Novel 4 ''-O-benzimidazolyl clarithromycin derivatives were designed, synthesized and evaluated for their in vitro antibacterial activities. These benzimidazolyl derivatives exhibited excellent activity against erythromycin-susceptible strains better than the references, and some of them showed greatly improved activity against erythromycin-resistant strains. Compounds 16 and 17, which have the terminal 2-(4-methylphenyl)benzimidazolyl and 2-(2-methoxyphenyl)benzimidazolyl groups on the C-4 '' bishydrazide side chains, were the most active against erythromycin-resistant Staphylococcus pneumoniae expressing the erm gene and the me! gene. In addition, compound 17 exhibited the highest activity against erythromycin-susceptible S. pneumoniae ATCC49619 and Staphylococcus aureus ATCC25923 as well. It is worth noting that the 4 ''-O-(2-aryl)benzimidazolyl derivatives show higher activity against erythromycin-susceptible and erythromycin-resistant strains than the 4 ''-O-(2-alkyl) benzimidazolyl derivatives. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.04.004
• 作为产物：
  描述：

  2-三氟甲基-1H-苯并咪唑-5-羧酸 在 硫酸 、 一水合肼 作用下， 以 甲醇 为溶剂， 反应 10.0h， 生成 2-三氟甲基-1H-苯并咪唑-5-碳酰肼
  参考文献：
  名称：

  Synthesis and antibacterial activity of novel 4″-O-benzimidazolyl clarithromycin derivatives

  摘要：

  Novel 4 ''-O-benzimidazolyl clarithromycin derivatives were designed, synthesized and evaluated for their in vitro antibacterial activities. These benzimidazolyl derivatives exhibited excellent activity against erythromycin-susceptible strains better than the references, and some of them showed greatly improved activity against erythromycin-resistant strains. Compounds 16 and 17, which have the terminal 2-(4-methylphenyl)benzimidazolyl and 2-(2-methoxyphenyl)benzimidazolyl groups on the C-4 '' bishydrazide side chains, were the most active against erythromycin-resistant Staphylococcus pneumoniae expressing the erm gene and the me! gene. In addition, compound 17 exhibited the highest activity against erythromycin-susceptible S. pneumoniae ATCC49619 and Staphylococcus aureus ATCC25923 as well. It is worth noting that the 4 ''-O-(2-aryl)benzimidazolyl derivatives show higher activity against erythromycin-susceptible and erythromycin-resistant strains than the 4 ''-O-(2-alkyl) benzimidazolyl derivatives. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.04.004

文献信息

• Inhibition of Shikimate Kinase from Methicillin-Resistant Staphylococcus aureus by Benzimidazole Derivatives. Kinetic, Computational, Toxicological, and Biological Activity Studies
  作者：Lluvia Rios-Soto、Alicia Hernández-Campos、David Tovar-Escobar、Rafael Castillo、Erick Sierra-Campos、Mónica Valdez-Solana、Alfredo Téllez-Valencia、Claudia Avitia-Domínguez

  DOI：10.3390/ijms25105077

  日期：——

  Antimicrobial resistance (AMR) is one of the biggest threats in modern times. It was estimated that in 2019, 1.27 million deaths occurred around the globe due to AMR. Methicillin-resistant Staphylococcus aureus (MRSA) strains, a pathogen considered of high priority by the World Health Organization, have proven to be resistant to most of the actual antimicrobial treatments. Therefore, new treatments

  抗菌素耐药性（AMR）是现代最大的威胁之一。据估计，2019年全球有127万人因抗菌素耐药性死亡。耐甲氧西林金黄色葡萄球菌 (MRSA) 菌株是世界卫生组织高度重视的病原体，已被证明对大多数实际抗菌治疗具有耐药性。因此，需要新的治疗方法来应对这种日益严重的威胁。从这个角度来看，MRSA生存的一个重要代谢途径是莽草酸途径，而哺乳动物中不存在这种途径，该途径参与分支酸的生物合成，分支酸是芳香族氨基酸、叶酸和泛醌合成的中间体。因此，该途径的酶被认为是设计新型抗生素的良好靶点。该路线的第五步是由莽草酸激酶（SK）完成的。在本研究中，针对 MRSA 莽草酸激酶 (SaSK) 筛选了包含 170 种苯并咪唑衍生物的内部化学库。这项工作导致了第一个 SaSK 抑制剂的鉴定，并对具有最大抑制活性的两种抑制剂（C1 和 C2）进行了表征。动力学研究表明，这两种化合物对于 ATP 都是竞争性抑制剂，而对于莽草