3-benzyl-2-(4-chlorophenyl)quinazolin-4(3H)-one

• 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: 3-benzyl-2-(4-chlorophenyl)quinazolin-4(3H)-one
• 英文别名: 3-Benzyl-2-(4-chlorophenyl)quinazolin-4-one
• 化学式: C₂₁H₁₅ClN₂O
• 分子量: 346.816
• InChiKey: VHZYQXHDTPHBKU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  32.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-benzyl-2-(4-chlorophenyl)quinazolin-4(3H)-one 在 aluminum (III) chloride 作用下， 以 甲苯 为溶剂， 反应 0.5h， 以92%的产率得到2-(4-chlorophenyl)-4(3H)-quinazolinone
  参考文献：
  名称：

  Ligand-Free Pd-Catalyzed and Copper-Assisted C–H Arylation of Quinazolin-4-ones with Aryl Iodides under Microwave Heating

  摘要：

  A microwave-assisted method for the palladium-catalyzed direct arylation of quinazolin-4-one has been developed under copper-assistance. This method is applicable to a wide range of aryl iodides and substituted (2H)-quinazolin-4-ones. This protocol provides a simple and efficient way to synthesize biologically relevant 2-arylquinazolin-4-one backbones.

  DOI：

  10.1021/acs.orglett.5b00467
• 作为产物：
  描述：

  3-benzyl-2-(4-chlorophenyl)-2,3-dihydroquinazolin-4(1H)-one 在 100 U laccase from Trametes versicolor 、 氧气 、 1-羟基苯并三唑 作用下， 以 aq. buffer 为溶剂， 反应 10.0h， 以74%的产率得到3-benzyl-2-(4-chlorophenyl)quinazolin-4(3H)-one
  参考文献：
  名称：

  漆酶介导的串联氧化法从醇类合成喹唑啉酮

  摘要：

  本文描述了在温和条件下使用漆酶-介体系统通过串联反应合成喹唑啉酮的方法。该程序涉及漆酶催化的醇氧化为相应的醛，然后与等酸酐和多种胺进行环缩合，得到2,3-二氢喹唑啉-4（1 H）-酮，将其进一步氧化为有用的喹唑啉酮。产量。使用酶作为催化剂，使用O 2作为环境友好型氧化剂，使用柠檬酸盐缓冲液作为绿色溶剂，代表了一种新颖高效的一锅合成喹唑啉酮的方法。

  DOI：

  10.1002/adsc.201400103

文献信息

• Cu/Pd-Catalyzed C-2-H Arylation of ­Quinazolin-4(3<i>H</i>)-ones with (Hetero)aryl Halides
  作者：Julien Godeau、Marine Harari、Sylvain Laclef、Emmanuel Deau、Corinne Fruit、Thierry Besson

  DOI：10.1002/ejoc.201501129

  日期：2015.12

  The regiospecific C-2–H arylation of N-3-substituted quinazolin-4(3H)-ones with a wide range of aryl or (hetero)aryl halides under microwave irradiation was studied. A ligand-dependent palladium/copper bicatalytic system was developed and allowed direct cross-coupling with a variety of (hetero)aryl halides. This useful and scalable procedure promotes the construction of C(sp2)–C(sp2) bonds from arenes

  研究了在微波辐射下，N-3-取代的喹唑啉-4（3H）-酮与多种芳基或（杂）芳基卤化物的区域特异性C-2-H芳基化。开发了一种依赖于配体的钯/铜双催化系统，并允许与各种（杂）芳基卤化物直接交叉偶联。这种有用且可扩展的过程促进了从芳烃或（杂）芳烃和芳基或（杂）芳基溴化物和氯化物以一种省时的策略构建 C(sp2)–C(sp2) 键。还研究了使用碘苯将反应扩展到各种 N-3-取代的喹唑啉-4(3H)-酮以及该方法的范围和局限性。
• Synthesis, Anti-microbial and Molecular Docking Studies of Quinazolin-4(3H)-one Derivatives
  作者：Yahia Mabkhot、Munirah Al-Har、Assem Barakat、Fahad Aldawsari、Ali Aldalbahi、Zaheer Ul-Haq

  DOI：10.3390/molecules19078725

  日期：——

  In this work, synthesis, antimicrobial activities and molecular docking studies of some new series of substituted quinazolinone 2a–h and 3a–d were described. Starting form 2-aminobenzamide derivatives 1, a new series of quinazolinone derivatives has been synthesized, in high yields, assisted by microwave and classical methods. Some of these substituted quinazolinones were tested for their antimicrobial activity against Gram-negative bacteria (Pseudomonas aeruginosa and Esherichia coli) and Gram-positive bacteria (Staphylococcus aureus, and Bacillus subtilis), and anti-fungal activity against (Aspergillus fumigatus, Saccharomyces cervevisiae, and Candida albicans) using agar well diffusion method. Among the prepared products, 3-benzyl-2-(4-chlorophenyl)quinazolin-4(3H)-one (3a) was found to exhibits the most potent in vitro anti-microbial activity with MICs of 25.6 ± 0.5, 24.3 ± 0.4, 30.1 ± 0.6, and 25.1 ± 0.5 µg/mL against Staphylococcus aureus, Bacillus subtilis, Pseudomonas aeruginosa and Esherichia coli, respectively. Compound 3a was found to exhibits the most potent in vitro anti-fungal activity with MICs of 18.3 ± 0.6, 23.1 ± 0.4, and 26.1 ± 0. 5 µg/mL against Aspergillus fumigatus, Saccharomyces cervevisiae, and Candidaal bicans, respectively.

  在这项工作中，描述了一些新的取代喹唑啉酮2a–h和3a–d的合成、抗微生物活性及分子对接研究。从2-氨基苯甲酰胺衍生物1出发，通过微波辅助和经典方法，高效合成了一系列喹唑啉酮衍生物。其中一些取代喹唑啉酮通过琼脂孔扩散法测试了它们对革兰氏阴性菌（铜绿假单胞菌和大肠杆菌）和革兰氏阳性菌（金黄色葡萄球菌和枯草芽孢杆菌）以及抗真菌活性（烟曲霉、酿酒酵母和白色念珠菌）的抗微生物活性。在制备的产品中，3-苄基-2-(4-氯苯基)喹唑啉-4(3H)-酮（3a）表现出最强的体外抗微生物活性，对金黄色葡萄球菌、枯草芽孢杆菌、铜绿假单胞菌和大肠杆菌的MIC值分别为25.6 ± 0.5、24.3 ± 0.4、30.1 ± 0.6和25.1 ± 0.5 µg/mL。化合物3a还表现出最强的体外抗真菌活性，对烟曲霉、酿酒酵母和白色念珠菌的MIC值分别为18.3 ± 0.6、23.1 ± 0.4和26.1 ± 0.5 µg/mL。
• Efficient one-pot tandem synthesis and cytotoxicity evaluation of 2,3-disubstituted quinazolin-4(3H)-one derivatives
  作者：Hue Thi Buu Bui、Kiep Minh Do、Huy Tran Duc Nguyen、Hieu Van Mai、Thanh La Duc Danh、De Quang Tran、Hiroyuki Morita

  DOI：10.1016/j.tet.2021.132426

  日期：2021.10

  moderate to good yields (25–82%). Their syntheses were based on a one pot tandem ring opening procedure followed by iodine-catalyzed oxidative cyclization of isatoic anhydride with aldehydes, using water as the only solvent under both classical and microwave irradiation conditions. Cytotoxicity assays of the prepared compounds against three human cancer cell lines (HeLa, MCF-7, and A549) indicated that 2

  20 种 2,3-二取代喹唑啉-4(3 H )-one 衍生物1 – 20以中等至良好的产率 (25–82%) 成功合成。他们的合成基于一锅串联开环程序，然后是碘催化的靛红酸酐与醛的氧化环化，在经典和微波辐射条件下使用水作为唯一溶剂。针对三种人癌细胞系（HeLa细胞，MCF-7，和A549）制备的化合物的细胞毒性测定法表明，2，3，和20具有适度的活动对MCF-7细胞（IC 50 = 47.2 μM、43.9 μM 和 44.9 μM，分别）。针对 A549 细胞的良好细胞毒活性观察到3和8，IC 50值分别为 30.7 μM 和 29.8 μM，与阳性对照 5-氟尿嘧啶（5-FU，IC 50  = 27.9 μM）相当。此外，化合物4 对 A549 细胞系表现出比阳性对照 5-FU稍强的活性 (IC 50 = 23.6 μM)。
• Rhodium(II)-Catalyzed Carbenoid Insertion of<i>N</i>-Tosylhydrazones into Amide NH Bonds: An Efficient Approach to<i>N</i>³-Benzyl/Alkyl-2-arylquinazolinones
  作者：Rajaka Lingayya、Mari Vellakkaran、Kommu Nagaiah、Jagadeesh Babu Nanubolu

  DOI：10.1002/adsc.201500678

  日期：2016.1.7

  Dirhodium(II) acetate‐catalyzed reactions of N‐tosylhydrazones with dihydroquinazolinones bearing different types of NH bonds that give N3‐benzyl/alkyl‐2‐arylquinazolin‐4(3H)‐ones through Csp3N bond formation by oxidative dehydrogenation and insertion of rhodium‐carbenoid into amide NH bond are reported for the first time. This method features good to excellent yields, good functional group tolerance

  二铑（II），乙酸催化的反应Ñ与dihydroquinazolinones轴承不同类型的N个-tosylhydrazones  H键，给Ñ 3 -苄基/烷基-2- arylquinazolin-4（3 ħ） -酮至C SP 3  N键形成通过氧化脱氢和铑卡宾插入酰胺ñ  H键报道首次。该方法具有良好至优异的产率，良好的官能团耐受性，高区域选择性和易于获得的起始原料的特征。
• One Pot Synthesis of 4(3<i>H</i>)‐Quinazolinones
  作者：Bashir A. Bhat、Devi P. Sahu

  DOI：10.1081/scc-120038496

  日期：2004.12.31

  Anthranilamides undergo cyclocondensation with aldehydes in presence of iodine in a single-pot reaction to afford 2-substituted 4(3H)-quinazolinones in moderate to excellent yield (40-95%). 2,3-Substituted 4(3H)-quinazolinones are synthesized in moderate to good yield by three-component condensation of isotoic anhydride, amine, and aldehyde in presence of iodine.