2-(4-bromophenyl)-4-phenyl-1,2-dihydroquinazoline | 1522379-06-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 2-(4-bromophenyl)-4-phenyl-1,2-dihydroquinazoline
• 英文别名: 2-(4-Bromophenyl)-4-phenyl-1,2-dihydroquinazoline
• CAS: 1522379-06-1
• 化学式: C₂₀H₁₅BrN₂
• 分子量: 363.256
• InChiKey: RUXTWQUMUIHDBH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.41
• 重原子数：
  23.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  24.39
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  对溴苯甲醛 、 2-氨基二苯甲酮 在 4-二甲氨基吡啶 、 ammonium acetate 作用下， 以 乙醇 为溶剂， 反应 1.5h， 以80%的产率得到2-(4-bromophenyl)-4-phenyl-1,2-dihydroquinazoline
  参考文献：
  名称：

  DMAP催化的一锅三组分方案温和有效地合成1,2-二氢喹唑啉

  摘要：

  描述了一种有效且简单的方法，可在温和的条件下由易于获得的芳族或杂芳族醛，2-氨基二苯甲酮和乙酸铵催化4-（N，N-二甲基氨基）吡啶（DMAP）合成1,2-二氢喹唑啉。讨论了该方法的范围和局限性。

  DOI：

  10.1016/j.tetlet.2013.10.157

文献信息

• A DMAP-catalyzed mild and efficient synthesis of 1,2-dihydroquinazolines via a one-pot three-component protocol
  作者：Chamseddine Derabli、Raouf Boulcina、Gilbert Kirsch、Bertrand Carboni、Abdelmadjid Debache

  DOI：10.1016/j.tetlet.2013.10.157

  日期：2014.1

  An efficient and simple method for the synthesis of 1,2-dihydroquinazolines catalyzed by 4-(N,N-dimethylamino)pyridine (DMAP) from readily available aromatic or heteroaromatic aldehydes, 2-aminobenzophenone, and ammonium acetate under mild conditions is described. The scope and limitations of the method are discussed.

  描述了一种有效且简单的方法，可在温和的条件下由易于获得的芳族或杂芳族醛，2-氨基二苯甲酮和乙酸铵催化4-（N，N-二甲基氨基）吡啶（DMAP）合成1,2-二氢喹唑啉。讨论了该方法的范围和局限性。
• Catalyst-free, one pot and three-component synthesis of 4′-phenyl-1′H-spiro[indoline-3,2′-quinazolin]-2-ones and 2,4-diphenyl-1,2-dihydroquinazolines
  作者：Ahmed Kamal、Korrapati Suresh Babu、Cheemalamarri Chandrasekhar、Burri Nagaraju、K.N. Visweswara Sastry、C. Ganesh Kumar

  DOI：10.1016/j.tetlet.2015.09.125

  日期：2015.11

  A simple, green, efficient and three-component procedure has been developed for the synthesis of 4'-pheny1'H-spiro[indoline-3,2'-quinazolin]-2-ones (4a-m and 6a-g) and 2,4-diphenyl-1,2-dihydroquinazolines (8a-I) by the reaction of 2-aminobenzophenones, isatins or aromatic benzaldehydes and ammonium acetate in excellent yields under catalyst-free conditions using ethanol as a solvent. This method provides several advantages such as operational simplicity, higher yields, shorter reaction time and catalyst-free conditions with ethanol as a solvent makes the method eco-friendly as well as economical. All the 4'pheny1'H-spiro[indoline-3,2'-quinazolin]-2-ones were tested for antimicrobial activity against both Gram-positive and Gram-negative bacterial strains including a fungal strain Candida albicans MTCC 3017. Among these, the compounds 4f, 6a, 6c and 6g showed appreciable antibacterial activity with MIC values 7.8 mu g/ml selectively against Gram-positive bacteria, Micrococcus luteus MTCC 2470. On the other hand, compounds 4j, 4m, 6c and 6g showed good activity with MIC values ranging between 3.9 and 7.8 mu g/ml against Gram-negative bacteria, Klebsiella planticota MTCC 530. (C) 2015 Elsevier Ltd. All rights reserved.
• Putta, Chandra Shekar; Lonka, Madhava Reddy; Ch, Krishna Reddy, Indian Journal of Heterocyclic Chemistry, 2017, vol. 27, # 1, p. 71 - 75
  作者：Putta, Chandra Shekar、Lonka, Madhava Reddy、Ch, Krishna Reddy

  DOI：——

  日期：——
• Potentiating the intracellular killing of Staphylococcus aureus by dihydroquinazoline analogues as NorA efflux pump inhibitor
  作者：Banani Deka、Mrinaly Suri、Sangita Sarma、Moirangthem Veigyabati Devi、Anamika Bora、Tejosmita Sen、Anjum Dihingia、Pallab Pahari、Anil Kumar Singh

  DOI：10.1016/j.bmc.2021.116580

  日期：2022.1

  convoluted the treatment process. Among different resistance mechanisms, efflux pump proteins play a central role and has made itself a direct approach for therapeutic exploration. To demarcate the role of dihydroquinazoline analogues as NorA efflux pump inhibitor in S. aureus1199B (NorA over producing) strain total seventeen analogues were synthesized and tested for their modulatory effects on norfloxacin

  金黄色葡萄球菌是一种新兴的人类病原体，由于其对多种药物的高耐药性而变得难以治疗。耐药菌株的出现使治疗过程更加复杂。在不同的耐药机制中，外排泵蛋白发挥着核心作用，并使其成为治疗探索的直接方法。界定二氢喹唑啉类似物作为 NorA 外排泵抑制剂在金黄色葡萄球菌中的作用1199B（NorA 过度生产）菌株共合成了 17 种类似物，并测试了它们对诺氟沙星和 Etbr 抗性的调节作用。还进行了进一步的积累测定、细菌时间杀灭动力学、细胞毒性测定。使用 THP-1 单核细胞确定类似物的细胞内杀伤能力，如 EPI。还预测了类似物与 NorA 的结合相互作用。二氢喹唑啉类似物显着降低了金黄色葡萄球菌中诺氟沙星和 Etbr 的 MIC1199B。除了它们非常低的毒性外，它们还分别显示出高的 Etbr 和诺氟沙星积累。在这些类似物存在的情况下，随着时间的推移，细菌杀灭动力学的对数进一步有效降低证实了它们作为 NorA