6-(4-methoxybenzyl)-6,6a-dihydroisoindolo[2,1-a]quinazoline-5,11-dione | 1308660-42-5

• 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: 6-(4-methoxybenzyl)-6,6a-dihydroisoindolo[2,1-a]quinazoline-5,11-dione
• 英文别名: 6-[(4-methoxyphenyl)methyl]-6aH-isoindolo[2,3-a]quinazoline-5,11-dione
• CAS: 1308660-42-5
• 化学式: C₂₃H₁₈N₂O₃
• 分子量: 370.408
• InChiKey: PZVXUIVCVYMLQK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  49.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-amino-N-(4-methoxybenzyl)benzamide 、 邻羧基苯甲醛 在 碘 作用下， 反应 3.0h， 以93%的产率得到6-(4-methoxybenzyl)-6,6a-dihydroisoindolo[2,1-a]quinazoline-5,11-dione
  参考文献：
  名称：

  碘催化的离子液体中异吲哚并[2,1-a]喹唑啉衍生物的合成

  摘要：

  对6,6的合成温和，绿色和简便方法一个-dihydroisoindolo [2,1-一个]喹唑啉-5,11-二酮衍生物以高产率使用离子液体作为绿色媒体进行说明。该方法涉及2-氨基苯甲酰胺与碘催化的2-甲酰基苯甲酸的反应，并提供了具有生物活性筛选潜力的新生物碱文库。

  DOI：

  10.1002/jhet.1696

文献信息

• Wang-OSO3H catalyzed green synthesis of bioactive isoindolo[2,1-a]quinazoline-5,11‑dione derivatives: An unexpected observation
  作者：G Dhananjaya、Rapolu Venkateshwarlu、Naresh Kumar Reddy Dinne、Avula Mahesh Kumar、Ramamohan Mekala、Venkateswara Rao Anna、Ravikumar Kapavarapu、Manojit Pal

  DOI：10.1016/j.molstruc.2021.131922

  日期：2022.2

  acidic catalyst for the synthesis of isoindolo[2,1-a]quinazoline-5,11-dione derivatives under green conditions. Thus the Wang-OSO3H catalyzed MCR of isatoic anhydride, 2-formylbenzoic acid and various amines in pure water afforded a range of desired product in good to excellent (86-94%) yield. The methodology can be performed under open air and is amenable for scale-up synthesis. The catalyst can be recovered

  磺酸官能化的 Wang 树脂 (Wang-OSO 3 H) 被探索作为一种聚合和可回收的酸性催化剂，用于在绿色条件下合成异吲哚并 [ 2,1- a ] 喹唑啉-5,11-二酮衍生物。因此，Wang-OSO 3H 催化的靛红酸酐、2-甲酰基苯甲酸和各种胺在纯水中的 MCR 以良好至极好的 (86-94%) 产率提供了一系列所需产物。该方法可以在露天下进行，并且适合放大合成。催化剂可多次回收和循环使用，其催化活性没有明显损失。在一种情况下观察到的 2-(1-羟基-3-氧代异吲哚啉-2-基)苯甲酰胺衍生物的意外形成可能允许通过使用适当的胺从相同的 MCR 获得此类杂环。计算机评估表明，已知的 TNF-α 抑制剂化合物4j可能是 SARS-CoV-2 的潜在配体，它通过其 OMe 和两个 C=O 基团与其形成 H 键。
• A new three-component reaction: green synthesis of novel isoindolo[2,1-a]quinazoline derivatives as potent inhibitors of TNF-α
  作者：K. Siva Kumar、P. Mahesh Kumar、K. Anil Kumar、M. Sreenivasulu、Ahamed A. Jafar、D. Rambabu、G. Rama Krishna、C. Malla Reddy、Ravikumar Kapavarapu、K. Shivakumar、K. Krishna Priya、Kishore V. L. Parsa、Manojit Pal

  DOI：10.1039/c1cc10715a

  日期：——

  Concurrent construction of five and six membered fused N-heretocyclic ring was achieved via a conceptually new three-component reaction affording 6,6a-dihydroisoindolo[2,1-a]quinazoline-5,11-diones as novel inhibitors of TNF-alphain vitro. This represents one of the few examples of direct TNF-alpha inhibition by small molecules.

  通过概念上新的三组分反应，实现了五元和六元稠合N-杂环的并发构建，从而提供了6,6a-二氢异吲哚并[2,1-a]喹唑啉-5,11-二酮类化合物作为体外TNF-α的新型抑制剂。这代表了小分子直接抑制TNF-α的少数几个例子之一。
• Studies on Novel Synthetic Methodologies, Part XII: An Efficient One-Pot Access to 6,6a-Dihydroisoindolo[2,1-a]quinazoline-5,11-diones and 5-Phenylisoindolo[2,1-a]quinazolin-11(6aH)-ones
  作者：Koneni Sashidhara、Gopala Palnati、Ranga Dodda、Srinivasa Avula、Priyanka Swami

  DOI：10.1055/s-0032-1317761

  日期：——

  A simple and efficient procedure for the construction of 6,6a-dihydroisoindolo[2,1-a]quinazoline-5,11-dione and 5-phenylisoindolo[2,1-a]quinazolin-11(6aH)-one derivatives in acetic acid under catalyst-free conditions is described. Attractive features of this methodology are its versatility, ready availability of starting materials and the efficiency in creating a complex core in a single operation.
• β-Cyclodextrin mediated MCR in water: synthesis of dihydroisoindolo[2,1-a]quinazoline-5,11-dione derivatives under microwave irradiation
  作者：G. Rajeshwar Reddy、T. Ram Reddy、R. Gangadhara Chary、Suju C. Joseph、Soumita Mukherjee、Manojit Pal

  DOI：10.1016/j.tetlet.2013.09.138

  日期：2013.12

  We report a faster and greener approach for the synthesis of dihydroisoindolo[2,1-a]quinazoline-5,11-dione derivatives of potential pharmacological interest via a beta-CD mediated MCR in water under microwave irradiation. (C) 2013 Elsevier Ltd. All rights reserved.
• Metal–Catalyst-Free Green and efficient synthesis of five and six membered fused N-heterocyclic quinazoline derivatives
  作者：M.V. Madhubabu、R. Shankar、G. Rajeshwar Reddy、T. Srinivasa Rao、Mandava V. Basaveswara Rao、Raghunadh Akula

  DOI：10.1016/j.tetlet.2016.09.094

  日期：2016.11

  An efficient and green approach has been developed for the construction of Tetracyclic nitrogen-bridgehead compounds were designed and synthesized in good yields. The reaction of easily prepared 3-bromoisobenzofuran-1(3H)-one with isatoic anhydride and amines gave the desired isoindoloquinazolinone derivatives in moderate to good yields. It is also amenable for scale-up. (C) 2016 Elsevier Ltd. All rights reserved.