2-(4-(benzyloxy)phenyl)-2,3-dihydroquinazolin-4(1H)-one | 359601-60-8

• 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-(benzyloxy)phenyl)-2,3-dihydroquinazolin-4(1H)-one
• 英文别名: 2-(4-phenylmethoxyphenyl)-2,3-dihydro-1H-quinazolin-4-one
• CAS: 359601-60-8
• 化学式: C₂₁H₁₈N₂O₂
• 分子量: 330.386
• InChiKey: QRWSPZKNYHKHPY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  50.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-苄氧基苯甲醛 、 2-氨基苯甲酰胺 在 2Nd⁽³⁺⁾*5H₂O*2C₁₇H₇O₉^(3-) 作用下， 以 乙腈 为溶剂， 以100%的产率得到2-(4-(benzyloxy)phenyl)-2,3-dihydroquinazolin-4(1H)-one
  参考文献：
  名称：

  三维金属钕有机骨架催化醛氰基甲硅烷基化及2,3-二氢喹唑啉-4(1H)-酮衍生物的合成

  摘要：

  在这项工作中，成功合成了一种新型3D镧系金属有机骨架（Ln-MOF）Nd-cdip（H 4 cdip = 5,5'-羰基二间苯二甲酸），可用作氰基甲硅烷基化的高效多相催化剂和2,3-二氢喹唑啉-4(1 H)的合成)-一种在室温下基于 MOF 通道中路易斯酸位点的衍生物。此外，Nd-cdip在无溶剂条件下催化氰基甲硅烷基化反应时具有优异的转化数（500）。Nd-cdip 可以在上述两个反应中重复使用至少五次，而收率不会显着下降。利用与Nd-cdip具有相同结构和功能的Tb-cdip的发光特性，研究了Nd-cdip催化氰基甲硅烷基化的可能机理。此外，Nd-cdip 催化的两个反应均符合零级动力学。

  DOI：

  10.1021/acs.inorgchem.3c01230

文献信息

• Synthesis of New 2-Aryl Substituted 2,3-Dihydroquinazoline-4(1<i>H</i>)-ones Under Solvent-Free Conditions, Using Molecular Iodine as a Mild and Efficient Catalyst
  作者：Shahnaz Rostamizadeh、Ali Mohammad Amani、Reza Aryan、Hamid Reza Ghaieni、Nasrin Shadjou

  DOI：10.1080/00397910802178427

  日期：2008.9.29

  Abstract A simple, inexpensive, and efficient one-pot synthesis of 2,3-dihydroquinazoline-4(1H)-one derivatives under solvent-free conditions using a catalytic amount of iodine with excellent product yields is reported. This methodology provides easy, quantitative access to various 2,3-dihydroquinazoline-4(1H)-one derivatives, using commercially available iodine as a catalyst.

  摘要报道了在无溶剂条件下使用催化量的碘以优异的产品收率简单、廉价、高效地一锅法合成 2,3-二氢喹唑啉-4(1H)-one 衍生物。该方法使用市售碘作为催化剂，可以轻松、定量地获取各种 2,3-二氢喹唑啉-4(1H)-one 衍生物。
• Synthesis of Some Novel 2-Aryl-Substituted 2,3-Dihydroquinazolin-4(1H)-ones under Solvent-Free Conditions Using MCM-41-SO3H as a Highly Efficient Sulfonic Acid
  作者：Shahnaz Rostamizadeh、Gholam Mahdavinia、Ali Amani、Hamid Sepehrian、Samira Ebrahimi

  DOI：10.1055/s-0029-1218676

  日期：2010.4

  ordered mesoporous silica material MCM-41 with covalently anchored sulfonic acid groups located inside the mesochannels, was used as an acid catalyst for the rapid and ‘green’ synthesis of 2,3-dihydroquinazolin-4(1H)-one derivatives under solvent-free condition. This novel synthetic method offers several advantages, such as excellent yields, simple procedure, short reaction times, and mild reaction

  MCM-41-SO 3 H（有序介孔二氧化硅材料MCM-41，其介孔内具有共价锚定的磺酸基团）被用作酸催化剂，用于快速和“绿色”合成2,3-二氢喹唑啉-4（1在无溶剂条件下为H）一衍生物。这种新颖的合成方法具有许多优点，例如产率高，操作简单，反应时间短和反应条件温和。 MCM-41-SO 3 H-纳米催化剂-2,3-二氢喹唑啉酮-多组分反应-无溶剂条件
• An efficient one-pot solvent-free synthesis of 2,3-dihydroquinazoline-4(1H)-ones via Al/Al2O3 nanoparticles
  作者：M. Z. Kassaee、Shahnaz Rostamizadeh、Nasrin Shadjou、Elahe Motamedi、Maryam Esmaeelzadeh

  DOI：10.1002/jhet.506

  日期：2010.11

  An efficient one‐pot, solvent‐free method is reported for the synthesis of 2‐phenyl‐2,3‐dihydroquinazoline‐4(1H)‐one as well as its o‐Cl, o‐OMe, m‐Br, m‐NO2, p‐OH, p‐NO2, p‐CN, p‐PhCH2O, p‐Cl, p‐F, p‐Br, p‐Me, and o,m‐dichloro derivatives, using our “as‐prepared” arc discharge fabricated Al/Al2O3 nanoparticles. Compared with our previous report and other known methods, this route gives higher yields

  一个有效的单罐，无溶剂的方法被报告用于合成2-苯基-2,3-二氢喹唑啉-4（1H） -酮，以及其直径： -Cl，ø -OMe，米-Br，米- NO 2，p -OH，p -NO 2，p -CN，p -PhCH 2 O，p -Cl，p -F，p -Br，p -Me和邻，间-二氯衍生物，使用我们的“作为准备好的“电弧放电”制造的Al / Al 2 O 3纳米粒子。与我们之前的报告和其他已知方法相比，该方法在较短的反应时间下具有较高的收率，而其绿色催化剂在可调节的条件下，至少可循环使用四次，而催化活性略有下降。J.杂环化​​学。（2010）。
• Click Reaction: Highly Efficient Synthesis of 2,3-Dihydroquinazolin-4(1<i>H</i>)-ones
  作者：Ahmad Shaabani、Ali Maleki、Hamid Mofakham

  DOI：10.1080/00397910802213802

  日期：2008.10.22

  In this work, condensation reaction of 2-aminobenzamide with various alkyl, aryl, and alicyclic aldehydes or ketones to 2,3-dihydroquinazolin-4(1H)-one derivatives in the presence of a catalytic amount of ammonium chloride in ethanol at room temperature is described. This reaction can be classified as a click chemical synthesis because of its high yields, short reaction times, and green and efficient reaction medium.
• Discovery of potent and selective nonplanar tankyrase inhibiting nicotinamide mimics
  作者：Yves Nkizinkiko、B.V.S. Suneel Kumar、Variam Ullas Jeankumar、Teemu Haikarainen、Jarkko Koivunen、Chanduri Madhuri、Perumal Yogeeswari、Harikanth Venkannagari、Ezeogo Obaji、Taina Pihlajaniemi、Dharmarajan Sriram、Lari Lehtiö

  DOI：10.1016/j.bmc.2015.06.063

  日期：2015.8

  Diphtheria toxin-like ADP-ribosyltransferases catalyse a posttranslational modification, ADP-ribosylation and form a protein family of 17 members in humans. Two of the family members, tankyrases 1 and 2, are involved in several cellular processes including mitosis and Wnt/beta-catenin signalling pathway. They are often over-expressed in cancer cells and have been linked with the survival of cancer cells making them potential therapeutic targets. In this study, we identified nine tankyrase inhibitors through virtual and in vitro screening. Crystal structures of tankyrase 2 with the compounds showed that they bind to the nicotinamide binding site of the catalytic domain. Based on the co-crystal structures we designed and synthesized a series of tetrahydroquinazolin-4-one and pyridopyrimidin-4-one analogs and were subsequently able to improve the potency of a hit compound almost 100-fold (from 11 mu M to 150 nM). The most potent compounds were selective towards tankyrases over a panel of other human ARTD enzymes. They also inhibited Wnt/beta-catenin pathway in a cell-based reporter assay demonstrating the potential usefulness of the identified new scaffolds for further development. (C) 2015 Elsevier Ltd. All rights reserved.