N-(2-fluorophenyl)carbonohydrazonoyl dicyanide | 191353-21-6

• 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: N-(2-fluorophenyl)carbonohydrazonoyl dicyanide
• 英文别名: 2-[2-(2-Fluorophenyl)hydrazono]malononitrile；2-[(2-fluorophenyl)hydrazinylidene]propanedinitrile
• CAS: 191353-21-6
• 化学式: C₉H₅FN₄
• mdl: MFCD00042195
• 分子量: 188.164
• InChiKey: SDNFYXHVPYJZNC-UHFFFAOYSA-N

物化性质

• 沸点：
  280.9±42.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.73
• 重原子数：
  14.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  71.97
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N-(2-fluorophenyl)carbonohydrazonoyl dicyanide 在 sodium azide 、 三乙胺盐酸盐 作用下， 以 甲苯 为溶剂， 以86%的产率得到2-fluorophenylhydrazono-1H-tetrazol-5-yl-acetonitrile
  参考文献：
  名称：

  Synthesis and antimicrobial activity studies of some novel substituted phenylhydrazono-1H-tetrazol-5-yl-acetonitriles

  摘要：

  In this study, some substituted phenylhydrazono-1H-tetrazol-5-yl-acetonitriles have been synthesized (2a-o, 2a and 2k are known compounds). The synthesized compounds were characterized by spectroscopic methods [Fourier-transform infrared (FTIR), nuclear magnetic resonance (NMR), mass spectroscopy (MS)]. In addition, antimicrobial activities of synthesized compounds were investigated against Bacillus cereus RSKK 863, Escherichia coli ATCC 3521, Pseudomonas aeruginosa ATCC 2921, and Staphylococcus aureus TP32. These compounds had antimicrobial effect against these bacteria (except for 2l).

  DOI：

  10.1007/s00044-009-9177-9
• 作为产物：
  描述：

  2-氟苯胺 、 丙二腈 在 盐酸 、 sodium nitrite 、 sodium acetate 作用下， 以 水 为溶剂， 反应 1.5h， 生成 N-(2-fluorophenyl)carbonohydrazonoyl dicyanide
  参考文献：
  名称：

  4-arylazo-3,5-diamino-1H-pyrazoles 的 SAR 研究：鉴定诱导铜绿假单胞菌生物膜分散的小分子

  摘要：

  通过筛选 50 000 种小分子化合物的集合，我们最近将 4-arylazo-3,5-diamino-1 H -pyrazoles 鉴定为一组新型抗生物膜剂。在这里，我们报告了一项基于 60 种类似物的 SAR 研究，通过检查可以进一步优化药效团的方法，例如通过芳环中的取代。SAR 研究揭示了非常有效的抗生物膜化合物 4-(2-(2-fluorophenyl)hydrazineylidene)-5-imino-4,5-dihydro-1 H -pyrazol-3-amine ( 2 )。

  DOI：

  10.1039/d1md00275a

文献信息

• Discovery, SAR study and ADME properties of methyl 4-amino-3-cyano-1-(2-benzyloxyphenyl)-1<i>H</i>-pyrazole-5-carboxylate as an HIV-1 replication inhibitor
  作者：Jeanne Fichez、Cathia Soulie、Laurent Le Corre、Sophie Sayon、Stéphane Priet、Karine Alvarez、Olivier Delelis、Patrick Gizzi、Guillaume Prestat、Christine Gravier-Pelletier、Anne-Geneviève Marcelin、Vincent Calvez、Patricia Busca

  DOI：10.1039/d0md00025f

  日期：——

  screened our in-house library of pyrazole-based compounds to evaluate their in cellulo activity against HIV-1 replication. Two hits with very similar structures appeared from single and multiple-round infection assays to be non-toxic and active in a dose-dependent manner. Chemical expansion of their series allowed an in-depth and consistent structure–activity-relationship study (SAR) to be built. Further

  受已知基于吡唑的 HIV 抑制剂的抗病毒活性的启发，我们筛选了我们内部的基于吡唑的化合物库，以评估它们在纤维素中对 HIV-1 复制的活性。从单轮和多轮感染测定中显示出具有非常相似结构的两个命中是无毒的并且以剂量依赖性方式具有活性。他们系列的化学扩展允许建立深入和一致的结构-活性-关系研究 (SAR)。进一步的 ADME 评估导致选择了 4-amino-3-cyano-1-(2-benzyloxyphenyl)-1 H-pyrazole-5-carboxylate 具有有利的药代动力学特征。最后，对其作用方式的检查表明，该化合物不属于三种主要的抗 HIV 药物，这是在病毒耐药性背景下最令人感兴趣的特征。
• [EN] COMPOUNDS HAVING PSEUDOMONAS ANTI-BIOFILM PROPERTIES<br/>[FR] COMPOSÉS AYANT DES PROPRIÉTÉS ANTI-BIOFILM DE PSEUDOMONAS
  申请人：UNIV COPENHAGEN

  公开号：WO2022043503A1

  公开（公告）日：2022-03-03

  The present invention relates to c-di-GMP lowering chemical compounds having anti- biofilm properties. In particular, the present invention relates to anti-biofilm compounds or salts or tautomers thereof for use in treatment and/or prevention of bacterial biofilm infection in human subjects caused by biofilm-forming bacteria of the genus Pseudomonas, in particular Pseudomonas spp. including P. aeruginosa. Methods of treating such infections in human subjects are contemplated as well. The present inventions further relates to the use of an anti-biofilm compound or a salt or tautomer thereof for dispersing biofilms in industrial water systems.

  本发明涉及具有抗生物膜特性的c-di-GMP降低化合物。具体而言，本发明涉及用于治疗和/或预防由假单胞菌属细菌引起的人体细菌生物膜感染的抗生物膜化合物或其盐或互变异构体，特别是包括P. aeruginosa在内的假单胞菌属细菌。还考虑了治疗人体细菌感染的方法。本发明还涉及使用抗生物膜化合物或其盐或互变异构体来分散工业水系统中的生物膜。
• SAR study of 4-arylazo-3,5-diamino-1<i>H</i>-pyrazoles: identification of small molecules that induce dispersal of <i>Pseudomonas aeruginosa</i> biofilms
  作者：Charlotte U. Jansen、Jesper Uhd、Jens B. Andersen、Louise D. Hultqvist、Tim H. Jakobsen、Martin Nilsson、Thomas E. Nielsen、Michael Givskov、Tim Tolker-Nielsen、Katrine M. Qvortrup

  DOI：10.1039/d1md00275a

  日期：——

  4-arylazo-3,5-diamino-1H-pyrazoles as a novel group of anti-biofilm agents. Here, we report a SAR study based on 60 analogues by examining ways in which the pharmacophore can be further optimized, for example, via substitutions in the aryl ring. The SAR study revealed the very potent anti-biofilm compound 4-(2-(2-fluorophenyl)hydrazineylidene)-5-imino-4,5-dihydro-1H-pyrazol-3-amine (2).

  通过筛选 50 000 种小分子化合物的集合，我们最近将 4-arylazo-3,5-diamino-1 H -pyrazoles 鉴定为一组新型抗生物膜剂。在这里，我们报告了一项基于 60 种类似物的 SAR 研究，通过检查可以进一步优化药效团的方法，例如通过芳环中的取代。SAR 研究揭示了非常有效的抗生物膜化合物 4-(2-(2-fluorophenyl)hydrazineylidene)-5-imino-4,5-dihydro-1 H -pyrazol-3-amine ( 2 )。
• Synthesis and antimicrobial activity studies of some novel substituted phenylhydrazono-1H-tetrazol-5-yl-acetonitriles
  作者：Serkan Yavuz、Özlem Aydın、Servet Çete、Ali Dişli、Yılmaz Yıldırır

  DOI：10.1007/s00044-009-9177-9

  日期：2010.3

  In this study, some substituted phenylhydrazono-1H-tetrazol-5-yl-acetonitriles have been synthesized (2a-o, 2a and 2k are known compounds). The synthesized compounds were characterized by spectroscopic methods [Fourier-transform infrared (FTIR), nuclear magnetic resonance (NMR), mass spectroscopy (MS)]. In addition, antimicrobial activities of synthesized compounds were investigated against Bacillus cereus RSKK 863, Escherichia coli ATCC 3521, Pseudomonas aeruginosa ATCC 2921, and Staphylococcus aureus TP32. These compounds had antimicrobial effect against these bacteria (except for 2l).