3-[(4-甲基哌嗪-1-基)甲基]-5,5-二(苯基)咪唑烷-2,4-二酮 | 21598-58-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 中文名称: 3-[(4-甲基哌嗪-1-基)甲基]-5,5-二(苯基)咪唑烷-2,4-二酮
• 英文名称: 3-((4-methylpiperazin-1-yl)methyl)-5,5-diphenylimidazolidine-2,4-dione
• 英文别名: 3-(4-methyl-piperazin-1-ylmethyl)-5,5-diphenyl-imidazolidine-2,4-dione；Hydantoin, 5,5-diphenyl-3-((4-methylpiperazinyl)methyl)-；3-[(4-methylpiperazin-1-yl)methyl]-5,5-diphenylimidazolidine-2,4-dione
• CAS: 21598-58-3
• 化学式: C₂₁H₂₄N₄O₂
• 分子量: 364.447
• InChiKey: KNVIWKFOCCEBOC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  联苯甲酰 以 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.58h， 生成 3-[(4-甲基哌嗪-1-基)甲基]-5,5-二(苯基)咪唑烷-2,4-二酮
  参考文献：
  名称：

  微波辅助生物筛选合成新型有效的抗菌和抗真菌化合物

  摘要：

  乙内酰脲已被广泛用作抗心律失常药，抗惊厥药和抗肿瘤药，但最近的研究表明乙内酰脲及其衍生物具有不同而新颖的细胞毒活性，即抗HIV，抗菌和抗真菌。以下研究文章涉及通过Mannich反应合成乙内酰脲及其衍生物，即3-（取代）-5,5-二苯基咪唑烷-2,4-二酮和1-（取代）-3,5,5-三苯基咪唑烷-2,4-二酮 合成的化合物是新颖的，某些化合物具有与所用标准品相同的良好的抗菌和抗真菌活性。所有合成步骤均在微波中进行，而不是通过常规方法进行，这导致了该方法的快速过程和高收率。

  DOI：

  10.1007/s00044-011-9611-7

文献信息

• Synthesis and pharmacological evaluation of novel N-Mannich bases derived from 5,5-diphenyl and 5,5-di(propan-2-yl)imidazolidine-2,4-dione core
  作者：Anna Czopek、Hanna Byrtus、Agnieszka Zagórska、Joanna Rychtyk、Małgorzata Góra、Kinga Sałat、Anna Rapacz、Jolanta Obniska

  DOI：10.1016/j.bmcl.2019.06.001

  日期：2019.8

  The aim of this study was to design and synthesize two series of N-Mannich bases with imidazolidine-2,4-dione core as a potential anticonvulsant with reduced toxicity and broad antiseizure activity. Preliminary screening revealed that the majority of synthesized compounds were effective in the maximal electroshock seizure (MES) and/or subcutaneous pentylenetetrazole (scPTZ) test. The most active in vivo compound, 18 (3-((4-methylpiperazin-1-yl)methyl)-5,5-diphenylimidazolidine-2,4-dione), exhibited an ED50 value comparable to that of phenytoin in the MES test (38.5 mg/kg vs 28.1 mg/kg), and more importantly, it showed four times higher potency than phenytoin in the 6 Hz test (12.2 mg/kg vs > 60 mg/kg). Additionally, 18 exhibited antiallodynic properties in the von Frey test in neuropathic (oxaliplatin-treated) mice. Compound 18 also demonstrated a broader spectrum of anticonvulsant activity than phenytoin and showed statistically significant antinociceptive properties in selected models of chronic pain.
• Microwave-assisted synthesis of some novel and potent antibacterial and antifungal compounds with biological screening
  作者：Mayank Bapna、Bharat Parashar、Vinod K. Sharma、Lalit S. Chouhan

  DOI：10.1007/s00044-011-9611-7

  日期：2012.7

  different and novel cytotoxic activity of hydantoins and its derivatives, i.e. anti HIV, antibacterial and antifungal. The following research article deals with the synthesis of hydantoins and their derivatives by Mannich reaction viz., 3-(substituted)-5,5-diphenylimidazolidine-2,4-dione and 1-(substituted)-3,5,5-triphenylimidazolidine-2,4-dione. The synthesised compounds are novel and some of the compounds

  乙内酰脲已被广泛用作抗心律失常药，抗惊厥药和抗肿瘤药，但最近的研究表明乙内酰脲及其衍生物具有不同而新颖的细胞毒活性，即抗HIV，抗菌和抗真菌。以下研究文章涉及通过Mannich反应合成乙内酰脲及其衍生物，即3-（取代）-5,5-二苯基咪唑烷-2,4-二酮和1-（取代）-3,5,5-三苯基咪唑烷-2,4-二酮 合成的化合物是新颖的，某些化合物具有与所用标准品相同的良好的抗菌和抗真菌活性。所有合成步骤均在微波中进行，而不是通过常规方法进行，这导致了该方法的快速过程和高收率。