8-(4-bromo-benzylidene)-4-(4bromophenyl)-5,6,7,8-tetrahydroquinazolin-2-ylamine | 1322199-52-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 8-(4-bromo-benzylidene)-4-(4bromophenyl)-5,6,7,8-tetrahydroquinazolin-2-ylamine
• 英文别名: 4-(4-bromophenyl)-8-[(4-bromophenyl)methylidene]-6,7-dihydro-5H-quinazolin-2-amine
• CAS: 1322199-52-9
• 化学式: C₂₁H₁₇Br₂N₃
• 分子量: 471.194
• InChiKey: BHDKXNMJOUEKDL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.13
• 重原子数：
  26.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  51.8
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  环己酮 、 对溴苯甲醛 在 sodium hydride 、 potassium hydroxide 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 8-(4-bromo-benzylidene)-4-(4bromophenyl)-5,6,7,8-tetrahydroquinazolin-2-ylamine
  参考文献：
  名称：

  Synthesis, molecular modeling and bio-evaluation of cycloalkyl fused 2-aminopyrimidines as antitubercular and antidiabetic agents

  摘要：

  An economical and efficient one step synthesis of a series of 8-(arylidene)-4-(aryl)-5,6,7,8-tetrahydroquinazolin-2-ylamines and 9-(arylidene)-4-(aryl)-6,7,8,9-tetrahydro-5H-cycloheptapyrimidin-2-ylamines by the reaction of bis-benzylidene cycloalkanones and guanidine hydrochloride in presence of NaH has been developed. All the synthesized compounds were evaluated against Mycobacterium tuberculosis H(37)Rv strain and the a-glucosidase and glycogen phosphorylase enzymes. Few of the compounds have shown interesting in vitro activity with MIC up to 3.12 mu g/mL against M. tuberculosis and very good inhibition of a-glucosidase and glycogen phosphorylase enzymes. The most potent non toxic compound 40 exhibited about 58% ex vivo activity at MIC of 3.12 mu g/mL. The present study opens a new gate to synthesize antitubercular agents for diabetic TB patients. In silico docking studies indicate that mycobacterial dihydrofolate reductase is the possible target of these compounds. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.06.040

文献信息

• Eco-safe and expeditious approaches for synthesis of quinazoline and pyrimidine-2-amine derivatives using ionic liquids aided with ultrasound or microwave irradiation
  作者：Masoumeh Zakeri、Mohamed M. Nasef、Ebrahim Abouzari-Lotf

  DOI：10.1016/j.molliq.2014.09.018

  日期：2014.11

  Green approaches for efficient synthesis of quinazoline- and pyrimidine-2-amine derivatives were established based on the one-pot and three-component condensation of guanidine carbonate, cyclic ketones and aldehydes. These approaches involve the evaluation of the activity of several acidic ionic liquids (ILs) as organocatalysts under solvent-free medium in the microwave and as solvents and catalysts

  基于碳酸胍，环状酮和醛的一锅和三组分缩合，建立了高效合成喹唑啉和嘧啶-2-胺衍生物的绿色方法。这些方法涉及评估几种酸性离子液体（ILs）在微波中在无溶剂的情况下作为有机催化剂的活性以及在超声辐射中作为溶剂和催化剂的活性。根据包括IL的类型和数量，反应温度和时间在内的参数变化，评估反应中的取代醛和环酮的数量。与超声方法相比，发现微波中的无溶剂程序在化学收率和反应时间方面都更加有效。催化剂的可回收性，简便性，
• Synthesis, molecular modeling and bio-evaluation of cycloalkyl fused 2-aminopyrimidines as antitubercular and antidiabetic agents
  作者：Nimisha Singh、Sarvesh Kumar Pandey、Namrata Anand、Richa Dwivedi、Shyam Singh、Sudhir Kumar Sinha、Vinita Chaturvedi、Natasa Jaiswal、Arvind Kumar Srivastava、Priyanka Shah、M. Imran Siddiqui、Rama Pati Tripathi

  DOI：10.1016/j.bmcl.2011.06.040

  日期：2011.8

  An economical and efficient one step synthesis of a series of 8-(arylidene)-4-(aryl)-5,6,7,8-tetrahydroquinazolin-2-ylamines and 9-(arylidene)-4-(aryl)-6,7,8,9-tetrahydro-5H-cycloheptapyrimidin-2-ylamines by the reaction of bis-benzylidene cycloalkanones and guanidine hydrochloride in presence of NaH has been developed. All the synthesized compounds were evaluated against Mycobacterium tuberculosis H(37)Rv strain and the a-glucosidase and glycogen phosphorylase enzymes. Few of the compounds have shown interesting in vitro activity with MIC up to 3.12 mu g/mL against M. tuberculosis and very good inhibition of a-glucosidase and glycogen phosphorylase enzymes. The most potent non toxic compound 40 exhibited about 58% ex vivo activity at MIC of 3.12 mu g/mL. The present study opens a new gate to synthesize antitubercular agents for diabetic TB patients. In silico docking studies indicate that mycobacterial dihydrofolate reductase is the possible target of these compounds. (C) 2011 Elsevier Ltd. All rights reserved.