4-(4-(4-(dimethylamino)benzylidene)-5-oxo-2-phenyl-4,5-dihydro-1H-imidazol-1-yl)-N-(5-methylisoxazol-3-yl)benzenesulfonamide | 1366126-06-8

• 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-(4-(4-(dimethylamino)benzylidene)-5-oxo-2-phenyl-4,5-dihydro-1H-imidazol-1-yl)-N-(5-methylisoxazol-3-yl)benzenesulfonamide
• CAS: 1366126-06-8
• 化学式: C₂₈H₂₅N₅O₄S
• 分子量: 527.604
• InChiKey: NUOORTRJUJFXON-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.68
• 重原子数：
  38.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  108.11
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  苯甲酰氯 在 sodium acetate 、 乙酸酐 、 溶剂黄146 、 sodium hydroxide 作用下， 反应 12.0h， 生成 4-(4-(4-(dimethylamino)benzylidene)-5-oxo-2-phenyl-4,5-dihydro-1H-imidazol-1-yl)-N-(5-methylisoxazol-3-yl)benzenesulfonamide
  参考文献：
  名称：

  对一些新合成的三取代咪唑啉酮作为 VEGFR-2 抑制剂的见解

  摘要：

  合成了两个系列的十种新的 1,2,4-三取代咪唑啉-5-酮，并针对 MCF-7 乳腺癌和 A549 肺癌细胞系进行筛选，以测试其潜在的体外抗癌活性。结果显示，与 A549 细胞系相比，测试化合物对 MCF-7 细胞系具有优先活性。对最有前途的十种化合物（ 3a 、 3c 、 3f 、 3g 、 3h 、 3i 、 3j 、 6a 、 6f和6i ）进行VEGFR-2酶抑制活性测试，以进一步探讨其作用机制。与IC 50值分别为0.06 和0.12 μM 的索拉非尼和舒尼替尼相比，测试化合物在0.07 至0.36 μM 的微摩尔浓度下表现出显着的酶抑制作用。最有希望的候选物3j进一步评估了其细胞周期阶段、细胞凋亡诱导能力以及其抗增殖活性和内皮细胞迁移的抑制潜力，并通过细胞划痕测定进行了分析。此外，还进行了计算机研究来识别和检测结合姿势的稳定性。

  DOI：

  10.1021/acsmedchemlett.4c00095

文献信息

• Synthesis, <i>in silico</i> metabolic and toxicity prediction of some novel imidazolinones derivatives as potent anticonvulsant agents
  作者：N. S. Hari Narayana Moorthy、Vipin Saxena、C. Karthikeyan、Piyush Trivedi

  DOI：10.3109/14756366.2011.584191

  日期：2012.4.1

  A series of 1,2,4-trisubstituted 5-imidazolinone derivatives were synthesized by Erlenmeyer condensation of benzoylglycine (hippuric acid) with different aldehydes in the presence of sodium acetate and acetic anhydride. The derivatives of the compounds were prepared by condensation of some known sulpha drugs with 5-oxazolone derivatives. The anticonvulsant activity of the compounds was determined by the protection of pentylenetetrazole-induced convulsions that was ranged from 10 to 60%. The compounds with p-OCH3, p-OH and o-Cl substitutions in the phenyl ring on 4(th) position of the imidazolinone ring exhibited good anticonvulsant activity. In silico metabolic and toxicity studies showed that all the compounds in the series are not likely to exhibit toxicity except the compounds IIIa, IIIb, VIa and VIb, that is predicted to show 29% mutagenicity and 53% irritation in comparison to the other compounds. The predicted lethal effect and hERG toxicity of the compounds showed that IIa, IVa, Va and Vb might be toxic at higher concentrations. The results successfully establish the synthesized imidazolinone derivatives as novel compounds with anticonvulsant properties, low predicted cardiotoxicity and lethal effects thus can be promising leads for further development as novel anticonvulsants.