6-(2-hydroxyethyl)-6,6a-dihydroisoindolo[2,1-a]quinazoline-5,11-dione | 1308660-40-3

• 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-(2-hydroxyethyl)-6,6a-dihydroisoindolo[2,1-a]quinazoline-5,11-dione
• 英文别名: 6-(2-hydroxyethyl)-6aH-isoindolo[2,3-a]quinazoline-5,11-dione
• CAS: 1308660-40-3
• 化学式: C₁₇H₁₄N₂O₃
• 分子量: 294.31
• InChiKey: CWGIHUKKVIGOGZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  60.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  靛红酸酐 、 C.I.酸性橙108 、 邻羧基苯甲醛 在 Montmorillonite K₁₀ 作用下， 以 乙醇 为溶剂， 反应 8.0h， 以95%的产率得到6-(2-hydroxyethyl)-6,6a-dihydroisoindolo[2,1-a]quinazoline-5,11-dione
  参考文献：
  名称：

  一种新的三组分反应：绿色合成新型异吲哚并[2,1-a]喹唑啉衍生物作为TNF-α的有效抑制剂。

  摘要：

  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。

  DOI：

  10.1039/c1cc10715a

文献信息

• 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.
• Saccharomyces cerevisiae catalyzed one pot synthesis of isoindolo[2,1-a]quinazoline performed under ultrasonication
  作者：Jemin R. Avalani、Devji S. Patel、Dipak K. Raval

  DOI：10.1016/j.molcatb.2013.01.024

  日期：2013.6

  An efficient and simple one pot method has been developed for the synthesis of isoindolo[2,1-a]quinazolines using Saccharomyces cerevisiae (baker's yeast) as a whole cell biocatalyst at room temperature. The synergetic effect of baker's yeast and ultrasound irradiation has been discussed. (C) 2013 Elsevier B.V. All rights reserved.
• 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。