(S)-4-butyl-3-(4-cyclohexylbutyl)-1-(4-((S)-2-imino-3-(3-(trifluoromethyl)phenethyl)imidazolidin-4-yl)butyl)imidazolidin-2-imine

• 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: (S)-4-butyl-3-(4-cyclohexylbutyl)-1-(4-((S)-2-imino-3-(3-(trifluoromethyl)phenethyl)imidazolidin-4-yl)butyl)imidazolidin-2-imine
• 英文别名: (5S)-5-[4-[(4S)-4-butyl-3-(4-cyclohexylbutyl)-2-iminoimidazolidin-1-yl]butyl]-1-[2-[3-(trifluoromethyl)phenyl]ethyl]-4,5-dihydroimidazol-2-amine
• 化学式: C₃₃H₅₃F₃N₆
• 分子量: 590.819
• InChiKey: BBSQFOUMGPEZNH-KYJUHHDHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  42
• 可旋转键数：
  16
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  72
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  溴化氰 、 环已烷丁酸 、 间三氟甲基苯乙酸 、 N-Boc-L-正亮氨酸 、 Fmoc-Lys(Boc)-NH2 在 1-羟基苯并三唑 、 N,N'-二异丙基碳二亚胺 、 哌啶 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.33h， 生成 (S)-4-butyl-3-(4-cyclohexylbutyl)-1-(4-((S)-2-imino-3-(3-(trifluoromethyl)phenethyl)imidazolidin-4-yl)butyl)imidazolidin-2-imine
  参考文献：
  名称：

  Combinatorial Libraries As a Tool for the Discovery of Novel, Broad-Spectrum Antibacterial Agents Targeting the ESKAPE Pathogens

  摘要：

  Mixture based synthetic combinatorial libraries offer a tremendous enhancement for the rate of drug discovery, allowing the activity of millions of compounds to be assessed through the testing of exponentially fewer samples. In this study, we used a scaffold-ranking library to screen 37 different libraries for antibacterial activity against the ESKAPE pathogens. Each library contained between 10000 and 750000 structural analogues for a total of >6 million compounds. From this, we identified a bis-cyclic guanidine library that displayed strong antibacterial activity. A positional scanning library for these compounds was developed and used to identify the most effective functional groups at each variant position. Individual compounds were synthesized that were broadly active against all ESKAPE organisms at concentrations <2 mu M. In addition, these compounds were bactericidal, had antibiofilm effects, showed limited potential for the development of resistance, and displayed almost no toxicity when tested against human lung cells and erythrocytes. Using a murine model of peritonitis, we also demonstrate that these agents are highly efficacious in vivo.

  DOI：

  10.1021/jm501628s

文献信息

• Bis-cyclic guanidine compound compositions, methods of use and treatment thereof
  申请人：University of South Florida

  公开号：US10052309B2

  公开（公告）日：2018-08-21

  The present disclosure provides compositions including a bis-cyclic guanidine compound, pharmaceutical compositions including a bis-cyclic guanidine compound, methods of treatment of a condition (e.g., bacterial infection) or disease, methods of treatment using compositions or pharmaceutical compositions, and the like.

  本公开提供了包括双环胍化合物的组合物、包括双环胍化合物的药物组合物、治疗病症（如细菌感染）或疾病的方法、使用组合物或药物组合物的治疗方法等。
• BIS-CYCLIC GUANIDINE COMPOUND COMPOSITIONS, METHODS OF USE AND TREATMENT THEREOF
  申请人：University of South Florida

  公开号：US20170065564A1

  公开（公告）日：2017-03-09

  The present disclosure provides compositions including a bis-cyclic guanidine compound, pharmaceutical compositions including a bis-cyclic guanidine compound, methods of treatment of a condition e.g., bacterial infection) or disease, methods of treatment using compositions or pharmaceutical compositions, and the like.
• US9782388B2
  申请人：——

  公开号：US9782388B2

  公开（公告）日：2017-10-10
• [EN] BIS-CYCLIC GUANIDINE COMPOUND COMPOSITIONS, METHODS OF USE AND TREATMENT THEREOF<br/>[FR] COMPOSITIONS DE COMPOSÉS DE GUANIDINE BIS-CYCLIQUE, MÉTHODES D'UTILISATION ET DE TRAITEMENT ASSOCIÉES
  申请人：UNIV SOUTH FLORIDA

  公开号：WO2015130547A1

  公开（公告）日：2015-09-03

  The present disclosure provides compositions including a bis-cyclic guanidine compound, pharmaceutical compositions including a bis-cyclic guanidine compound, methods of treatment of a condition e.g., bacterial infection) or disease, methods of treatment using compositions or pharmaceutical compositions, and the like.