2-(2,5-dimethoxyphenyl)-2,3-dihydroquinazolin-4(1H)-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: 2-(2,5-dimethoxyphenyl)-2,3-dihydroquinazolin-4(1H)-one
• 英文别名: 2-(2,5-dimethoxyphenyl)-2,3-dihydro-1H-quinazolin-4-one
• 化学式: C₁₆H₁₆N₂O₃
• 分子量: 284.315
• InChiKey: YPOYKSUHSTWRFF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  59.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2,5-dimethoxyphenyl)-2,3-dihydroquinazolin-4(1H)-one 在 potassium permanganate 作用下， 以 丙酮 为溶剂， 生成 2-(2,5-Dimethoxy-phenyl)-3H-quinazolin-4-one
  参考文献：
  名称：

  具有不饱和/饱和连接子的喹唑啉酮-苯基喹喔啉杂合物作为新型抗增殖剂。

  摘要：

  通过3-烯丙基-2-甲基喹唑啉-4（3H）-一（5a-n）与溴苯基）喹喔啉（8）的反应，以高收率高效合成了一系列新的新颖的喹唑啉酮与烯丙基苯基喹喔啉杂化物9a-n。 Pd催化了Heck交叉偶联，并评估了其对四种癌细胞系（例如HeLa（宫颈），MIAPACA（胰腺），MDA-MB-231（乳腺）和IMR32（神经母细胞瘤））的抗增殖活性。化合物9a，9e，9g和9h表现出有希望的抗增殖活性，对四种细胞系的GI50值为0.06至0.2μM，而化合物9e和9k对HeLa和MIAPACA细胞系以及化合物9b，9d，9h和9b表现出显着活性。图9j显示了针对IMR32和MDA-MB-231细胞系的选择性效力。这是关于E-2-（4-取代）-3-（3-（4-（喹喔啉-2-基）苯基）烯丙基）喹唑啉-4（3H）的合成和体外抗增殖评估的第一份报告）-个（9a-n）。对接结果表明实验活性与计算的结合亲和力（对接

  DOI：

  10.1016/j.bmcl.2016.05.021
• 作为产物：
  描述：

  2,5-二甲氧基苯甲醛 、 高邻苯二甲酸酐 在 ammonium acetate 作用下， 反应 0.17h， 以94%的产率得到2-(2,5-dimethoxyphenyl)-2,3-dihydroquinazolin-4(1H)-one
  参考文献：
  名称：

  在无催化剂和无溶剂条件下有效合成2,3-二氢喹唑啉-4（1H）-one衍生物

  摘要：

  据报道，在无溶剂和无催化剂的条件下，通过芳族醛，isatoic酸酐和乙酸铵的反应，一个简单，高效，方便的一锅合成2,3-dihydroquinazolin-4（1 H）-one衍生物。该方案的优点包括反应时间短，反应条件温和，后处理容易，收率高和环境友好。J.杂环化​​学。（2011）。

  DOI：

  10.1002/jhet.592

文献信息

• Probing the catalytic activity of highly efficient sulfonic acid fabricated cobalt ferrite magnetic nanoparticles for the clean and scalable synthesis of dihydro, spiro and bis quinazolinones
  作者：Priyanka Yadav、Satish K. Awasthi

  DOI：10.1039/d1nj01149a

  日期：——

  An exceptionally productive, rapid, simple, and eco-friendly approach for the synthesis of 2,3-dihydroquinazolin-4(1H)-one has been developed utilizing acidic magnetically retrievable cobalt ferrite nanoparticles (CFNP@SO₃H).

  一个异常高效、快速、简单且环保的方法已经开发出来，用于合成2,3-二氢喹唑啉-4(1H)-酮，利用了酸性可磁回收的钴铁氧化物纳米颗粒（CFNP@SO3H）。
• Silica Sulfuric Acid-coated Fe3O4 Nanoparticles as a Highly Efficient and Reusable Solid Acid Catalyst for the Green Synthesis of 2,3- Dihydroquinazolin-4(1H)-ones under Solvent-free Conditions
  作者：Monire Beyki、Mehdi Fallah-Mehrjardi

  DOI：10.2174/1570178614666170711144740

  日期：2017.12.11

  An efficient and eco-friendly procedure for the synthesis of 2,3-dihydroquinazolin-4(1H)- ones and spiroquinazolinones in the presence of sulfuric acid functionalized silica-coated magnetite nanoparticles under solvent-free conditions has been described. The reactions are completed in short times, and the products are obtained in high isolated yields without any undesirable side reaction. This method

  已经描述了在无溶剂条件下在硫酸官能化的二氧化硅包被的磁铁矿纳米粒子存在下合成2,3-二氢喹唑啉-4（1H）-和螺喹唑啉酮的有效且环保的方法。反应在短时间内完成，并且以高分离产率获得产物，而没有任何不希望的副反应。该方法具有几个优点，包括反应时间短，操作简便，后处理容易，环境友好的反应条件，高分离产率和催化剂的可重复使用性。可以容易地通过外部磁体将催化剂从反应混合物中分离和回收，并在随后的反应中重新使用而活性没有明显损失。
• Green Protocol for the Synthesis of 2-Aryl-2,3-dihydroquinazoline-4(1H)-ones Using Indion Ina 225H Resin
  作者：K. Satish Reddy、T. Parthasarathy、K. Santosh Kumar、Apuri Satyender

  DOI：10.14233/ajchem.2015.18362

  日期：——

  Synthesis of 2-aryl-2,3-dihydroquinazoline-4(1H)-ones is described by using new and novel heterogeneous catalyst, Indion Ina 225H resin. Anthranilamide was reacted with a series of aromatic aldehydes in presence of resin to afford various 2-aryl substituted 2,3-dihydroquinazoline-4(1H)-ones. The resin employed in these reactions can be recovered and reused.

  使用新型异相催化剂 Indion Ina 225H 树脂合成了 2-芳基-2,3-二氢喹唑啉-4(1H)-酮。在树脂存在下，蒽酰胺与一系列芳香醛发生反应，生成各种 2-芳基取代的 2,3-二氢喹唑啉-4(1H)-酮。在这些反应中使用的树脂可以回收和重复使用。
• 6-Alkylamino- and 2,3-Dihydro-3‘-methoxy-2-phenyl-4-quinazolinones and Related Compounds:  Their Synthesis, Cytotoxicity, and Inhibition of Tubulin Polymerization
  作者：Mann-Jen Hour、Li-Jiau Huang、Sheng-Chu Kuo、Yi Xia、Kenneth Bastow、Yuka Nakanishi、Ernest Hamel、Kuo-Hsiung Lee

  DOI：10.1021/jm000151c

  日期：2000.11.1

  As part of our continuing search for potential anticancer candidates among 2-phenyl-4-quinolones and 2-phenyl-4-quinazolinones, two series of 6,7,2',3',4',5'-substituted 2-phenyl-4-quinazolinones and 6,2',3',4',5'-substituted 2,3-dihydro-2-phenyl-4-quinazolinones were synthesized and evaluated for cytotoxicity and as inhibitors of tubulin polymerization. In general, a good correlation was found between the two activities. Five of the 6-substituted heterocyclic 2-phenyl-4-quinozolinones (37-51) showed significant cytotoxicity against a panel of human tumor cell lines with EC50 values in the low micromolar to nanomolar concentration ranges. Compound 38 was the most potent of these compounds, as well as the most potent inhibitor of tubulin polymerization in this series. The activity of 38 was in the same range as those of the antimitotic natural products, colchicine, podophyllotoxin, and combretastatin A-4. Substituted 2-phenyl-4-quinazolinones and 2,3-dihydro-2-phenyl-4-quinazolinones also displayed highly selective cytotoxicity against the ovarian cancer 1A9 and P-gp resistant KB-VIN cell lines.
• A Brønsted Acid Ionic Liquid Immobilized on Fe3O4@SiO2 Nanoparticles as an Efficient and Reusable Solid Acid Catalyst for the Synthesis of 2,3-Dihydroquinazolin-4(1H)-ones
  作者：M. Fallah-Mehrjardi、S. Kalantari

  DOI：10.1134/s1070428020020207

  日期：2020.2

  In the present study, an efficient and magnetically recoverable Bronsted acid ionic liquid, 1-methyl-3-[3-(triethoxysilyl)propyl]-1H-imidazol-3-ium hydrogen sulfate, immobilized on the surface of Fe3O4@SiO2 magnetic nanoparticles (Fe3O4@SiO2-ImHSO(4)) has been used for a high-yield synthesis of 2,3-dihydroquinazolin-4(1H)-ones through the condensation of anthranilamide with aldehydes and ketones in EtOH at room temperature or under reflux. The significant features of the present protocol are short reaction times, high yields of products, ecofriendly reaction conditions, simple work-up, and reusability of the catalyst. The catalyst can be simply magnetically recovered and reused at least five times without considerable loss of its catalytic activity.