2,2-dimethyl-5-{[(3-trifluoromethylphenyl)amino]methylene}-1,3-dioxane-4,6-dione | 25063-55-2

• 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: 2,2-dimethyl-5-{[(3-trifluoromethylphenyl)amino]methylene}-1,3-dioxane-4,6-dione
• 英文别名: 2,2-Dimethyl-5-[[3-(trifluoromethyl)anilino]methylidene]-1,3-dioxane-4,6-dione
• CAS: 25063-55-2
• 化学式: C₁₄H₁₂F₃NO₄
• mdl: MFCD00097070
• 分子量: 315.249
• InChiKey: ORBHFACPYMGTJD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2,2-dimethyl-5-{[(3-trifluoromethylphenyl)amino]methylene}-1,3-dioxane-4,6-dione 在 三氯氧磷 作用下， 以 二苯醚 为溶剂， 反应 3.08h， 生成 4-氯-7-三氟甲基喹啉
  参考文献：
  名称：

  Synthesis of ring-substituted 4-aminoquinolines and evaluation of their antimalarial activities

  摘要：

  A simple two-step synthesis method was used to make 51 B-ring-substituted 4-hydroxyquinolines allowing analysis of the effect of ring substitutions on inhibition of growth of chloroquine sensitive and resistant strains of Plasmodium falciparum, the dominant cause of malaria morbidity. Substituted quinoline rings other than the 7-chloroquinoline ring found in chloroquine were found to have significant activity against the drug-resistant strain of P. falciparum W2. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.12.037
• 作为产物：
  描述：

  丙二酸环(亚)异丙酯 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 2,2-dimethyl-5-{[(3-trifluoromethylphenyl)amino]methylene}-1,3-dioxane-4,6-dione
  参考文献：
  名称：

  Synthesis of ring-substituted 4-aminoquinolines and evaluation of their antimalarial activities

  摘要：

  A simple two-step synthesis method was used to make 51 B-ring-substituted 4-hydroxyquinolines allowing analysis of the effect of ring substitutions on inhibition of growth of chloroquine sensitive and resistant strains of Plasmodium falciparum, the dominant cause of malaria morbidity. Substituted quinoline rings other than the 7-chloroquinoline ring found in chloroquine were found to have significant activity against the drug-resistant strain of P. falciparum W2. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.12.037

文献信息

• Facile one-pot synthesis, butyrylcholinesterase and α-glucosidase inhibitory activities, structure–activity relationship, molecular docking and DNA–drug binding analysis of Meldrum’s acid derivatives
  作者：Haroon Mehfooz、Aamer Saeed、Muhammad Faisal、Fayaz Ali Larik、Urooj Muqadar、Saira Khatoon、Pervaiz Ali Channar、Hammad Ismail、Salma Bilquees、Sajid Rashid、Shagufta Shafique、Bushra Mirza、Erum Dilshad、Fawad Ahmad

  DOI：10.1007/s11164-020-04100-3

  日期：2020.5

  (IC50 = 4.7 mg/mL), whereas, in terms of BChE inhibitory activity investigation, the derivatives 3a and 3c showed novel results, with the IC50 values equal to 1.2 and 2.9 mg/mL, respectively, as compared to standard galantamine hydrobromide (IC50 = 4.7 mg/mL), making derivative 3a a dual inhibitor of both enzymes. Further, structure–activity relationship, comparative molecular docking analysis and the DNA–drug

  Meldrum的酸衍生物很容易通过一锅缩合法合成，并通过NMR（1 H，13 C，DEPT-90和DEPT-135）和EI-MS进行表征。筛选合成的化合物抑制丁酰胆碱酯酶（BChE）和α-葡萄糖苷酶的潜力。有趣的是，衍生物3a显示出有效的α-葡萄糖苷酶抑制活性，与标准阿卡波糖（IC 50  = 4.7 mg / mL）相比，IC 50值等于2.1 mg / mL ，而就BChE抑制活性而言，导数3a和3c显示了新颖的结果，IC 50与标准加兰他敏氢溴酸盐（IC 50  = 4.7 mg / mL）相比，分别等于1.2和2.9 mg / mL的值，制得衍生物3a两种酶的双重抑制剂。此外，研究了结构-活性关系，比较分子对接分析和DNA-药物结合相互作用，以研究化学结构与其生物学活性，机制抑制，化合物相互作用，DNA结合常数和吉布斯自由能之间的关系。抑制剂与α-葡萄糖苷酶和BuChE结合的结构见