4-oxo-5,5-diphenyl-4,5-dihydro-1H-imidazol-2-ylcyanamide | 169234-77-9

• 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: 4-oxo-5,5-diphenyl-4,5-dihydro-1H-imidazol-2-ylcyanamide
• 英文别名: (5-oxo-4,4-diphenyl-1H-imidazol-2-yl)cyanamide
• CAS: 169234-77-9；26975-74-6
• 化学式: C₁₆H₁₂N₄O
• 分子量: 276.297
• InChiKey: HSFDXMADWFHXEY-UHFFFAOYSA-N

物化性质

• 熔点：
  260-262 °C(Solv: acetone (67-64-1); water (7732-18-5))
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  77.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  copper(II) perchlorate hexahydrate 、 4-oxo-5,5-diphenyl-4,5-dihydro-1H-imidazol-2-ylcyanamide 在 aq. NH₃ 作用下， 以 甲醇 为溶剂， 以44%的产率得到bis(methyl N-(4-oxo-5,5-diphenyl-4,5-dihydro-1H-imidazol-2-yl)imidocarbamato)copper(II) hemihydrate
  参考文献：
  名称：

  Towards a system for the systematic structural study of intermolecular interactions in crystals of transition metal complexes

  摘要：

  报告了铜(II)和镍(II)的假大环配合物，其中一种配合物含有双齿配体 N-(4-氧代-5,5-二苯基-4,5-二氢-1H-咪唑-2-基)氨基甲酸甲酯和 N,N-二甲基-N′-(4-氧代-5,5-二苯基-4,5-二氢-1H-咪唑-2-基)胍、和 N,N-二甲基-N′-(4-氧代-5,5-二苯基-4,5-二氢-1H-咪唑-2-基)胍的 X 射线结构进行了比较。这些络合物的一个特点是能够形成氢键链或相邻络合物通过苯基 "环抱 "连接的链。此外，还讨论了配体结构的微小变化或从不同溶剂中结晶时产生的超分子结构变化。

  DOI：

  10.1039/b503381k
• 作为产物：
  描述：

  安息香精油 在 硫酸 、 sodium ethanolate 、 sodium bromide 作用下， 以 二甲基亚砜 为溶剂， 反应 2.0h， 生成 4-oxo-5,5-diphenyl-4,5-dihydro-1H-imidazol-2-ylcyanamide
  参考文献：
  名称：

  用于（5-氧代-4,4-二芳基咪唑烷-2-亚基）氰酰胺的合成和抗氧化活性研究的苯偶姻到苯偶酰的新型氧化系统

  摘要：

  摘要 在这项工作中，通过两种新方法从安息香1a-f制备苯偶酰衍生物2a-f，收率高且反应时间短；(i)将其与硫和吗啉的乙醇混合物回流，以及(ii)将其与氧化剂“DMSO-NaBr-H 2 SO 4体系”在85℃下搅拌。因此，在乙醇钠作为碱性催化剂存在下，苯偶酰2a -f与市售氰基胍反应，合成了一系列新的 (5-氧代-4,4-二芳基咪唑烷-2-亚基)氰酰胺 3a-f 。新产品3a-f表现出基于“体外”的良好抗氧化活性 ” 2,2-二苯基-1-三硝基苯肼 (DPPH) 与维生素 C 的比较分析。

  DOI：

  10.1080/00397911.2023.2224907

文献信息

• Design, Synthesis, and Antibacterial Screening of Some Novel Heteroaryl-Based Ciprofloxacin Derivatives as DNA Gyrase and Topoisomerase IV Inhibitors
  作者：Lamya H. Al-Wahaibi、Amer A. Amer、Adel A. Marzouk、Hesham A. M. Gomaa、Bahaa G. M. Youssif、Antar A. Abdelhamid

  DOI：10.3390/ph14050399

  日期：——

  Compounds 2–6, oxadiazole derivatives, were found to have antibacterial activity that was 88 to 120% that of ciprofloxacin against Gram-positive and Gram-negative bacteria. The findings showed that none of the compounds tested had antifungal activity against Aspergillus flavus, but did have poor activity against Candida albicans, ranging from 23% to 33% of fluconazole, with compound 3 being the most active

  使用1 H NMR，13 C NMR和元素分析合成了一系列包含各种杂环衍生物的新环丙沙星杂化物，并在结构上进行了阐明。以环丙沙星为参考，针对革兰氏阳性细菌菌株（如金黄色葡萄球菌和枯草芽孢杆菌）以及革兰氏阴性菌株（如大肠杆菌和铜绿假单胞菌）在体外筛选化合物1 – 21。结果，许多所检查的化合物具有与环丙沙星等效的抗细菌活性。化合物2 – 6发现恶二唑衍生物对革兰氏阳性和革兰氏阴性细菌的抗菌活性为环丙沙星的88％至120％。研究结果表明，所测试的化合物均未对黄曲霉具有抗真菌活性，但对白色念珠菌的活性较弱，占氟康唑的23％至33％，其中化合物3的活性最高（氟康唑的33％）。最有效的化合物，3，4，5和6，显示的IC 50的86，42，92，和180 nM的对大肠杆菌DNA促旋酶，分别为（新生霉素，IC 50 = 170纳米）。化合物4、5和6的IC 50与新霉素（IC 50 = 11 µM）相比，E。coli
• A systematic study of ligand intermolecular interactions in crystals of copper(II) complexes of bidentate guanidino derivatives
  作者：Michael M. Bishop、Leonard F. Lindoy、Mary McPartlin、Andrew Parkin、Oliver T. Thorn-Seshold、Peter Turner

  DOI：10.1016/j.poly.2006.06.043

  日期：2007.1

  Abstract The synthesis and X-ray structures of four neutral copper(II) complexes and one cationic complex incorporating bidentate alkyl N -(4-oxo-5,5-diphenyl-4,5-dihydro-1 H -imidazol-2-yl)imidocarbamate ligands are reported. The neutral complexes, which possess potential doublet (DA) hydrogen bonding motifs, form supramolecular structures based on synthons involving hydrogen bonding or phenyl embraces

  摘要四种中性铜（II）配合物和一种包含二齿烷基N-（4-氧代-5,5-二苯基-4,5-二氢-1 H-咪唑-2-基的阳离子配合物）的合成及X射线结构报道了亚氨基氨基甲酸酯配体。具有潜在的双峰（DA）氢键基序的中性络合物形成基于涉及氢键或苯基环的合成子的超分子结构。描述了通过这些合成子的结合在晶体内形成薄片的过程，以及在薄片之间的腔中捕获的客体分子的发生。阳离子络合物形成结合了硝酸根离子的扩展的氢键结构。将这五个复合物的结构与先前报道的相关配体复合物的结构进行了比较。
• Bioavailability and Anticonvulsant Activity of 2-Cyanoguanidinophenytoin, a Structural Analogue of Phenytoin
  作者：Didier M. Lambert、Bernard Masereel、Bernard Gallez、Muriel Geurts、Gerhard K.E. Scriba

  DOI：10.1021/js960093b

  日期：1996.10

  Phenytoin is extensively used in Europe and the United States for the treatment of generalized tonic clonic seizures (grand mal). However, the efficacy is lowered by the erratic bioavailability after oral administration. The current study was conducted in order to investigate the physicochemical properties, the bioavailability, and the anticonvulsant activity of cyanoguanidinophenytoin (CNG-DPH), a structural analogue of phenytoin, which was obtained by the replacement of the urea moiety by a cyanoguanidine moiety. CNG-DPH was prepared under homogeneous Blitz conditions and under heterogeneous phase-transfer conditions. CNG-DPH is poorly water soluble and has a pK(a) of 5.3. At pH 7.4, log P' was 1.16, from which a pH-independent log P of 3 can be calculated. Pharmacokinetic parameters were obtained after oral administration of CNG-DPH to rats and were compared to those of phenytoin after administration of an equimolar amount. AUC, t(max), and C-max were significantly increased compared to those of phenytoin. The anticonvulsant profile was similar to the profile of phenytoin. CNG-DPH was active in the maximal electroshock seizure test, albeit 7-fold less active than phenytoin. The analogue did not protect animals against convulsions induced by chemicals such as pentylenetetrazole, picrotoxin, N-methyl-aspartate, strychnine, and bicuculline. It is concluded that while the bioisosteric exchange of the urea moiety of the molecule with the cyanoguanidine moiety dramatically changed the physicochemical and pharmacokinetic parameters compared to those of phenytoin, the concomitant change of the affinity toward molecular targets reduced the pharmacological activity and the therapeutic efficacy of the compound.