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氢键辅助的三组分串联反应构建 - 烷基-4-喹诺酮。

Hydrogen Bond Assisted Three-Component Tandem Reactions to Access -Alkyl-4-Quinolones.

机构信息

State Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Medical University, Guiyang 550014, China.

The Key Laboratory of Chemistry for Natural Products of Guizhou Province and Chinese Academy of Sciences, Guiyang 550014, China.

出版信息

Molecules. 2023 Mar 2;28(5):2304. doi: 10.3390/molecules28052304.

DOI:10.3390/molecules28052304
PMID:36903552
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10005641/
Abstract

Hydrogen-bonding catalytic reactions have gained great interest. Herein, a hydrogen-bond-assisted three-component tandem reaction for the efficient synthesis of -alkyl-4-quinolones is described. This novel strategy features the first proof of polyphosphate ester (PPE) as a dual hydrogen-bonding catalyst and the use of readily available starting materials for the preparation of -alkyl-4-quinolones. The method provides a diversity of -alkyl-4-quinolones in moderate to good yields. The compound demonstrated good neuroprotective activity against -methyl-ᴅ-aspartate (NMDA)-induced excitotoxicity in PC12 cells.

摘要

氢键催化反应引起了广泛关注。在此,我们描述了一种氢键辅助的三组分串联反应,用于高效合成 -烷基-4-喹诺酮。该新策略的特点是首次证明多磷酸酯(PPE)作为双氢键催化剂,并使用易得的起始原料制备 -烷基-4-喹诺酮。该方法以中等至良好的收率提供了多种 -烷基-4-喹诺酮。化合物 对 PC12 细胞中 -甲基-D-天冬氨酸(NMDA)诱导的兴奋性毒性具有良好的神经保护活性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0b12/10005641/c35a7fd8fb40/molecules-28-02304-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0b12/10005641/6a81d4e0bd33/molecules-28-02304-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0b12/10005641/98f1d8a9ae77/molecules-28-02304-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0b12/10005641/c3adad432821/molecules-28-02304-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0b12/10005641/1e39766eced6/molecules-28-02304-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0b12/10005641/c35a7fd8fb40/molecules-28-02304-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0b12/10005641/6a81d4e0bd33/molecules-28-02304-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0b12/10005641/98f1d8a9ae77/molecules-28-02304-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0b12/10005641/c3adad432821/molecules-28-02304-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0b12/10005641/1e39766eced6/molecules-28-02304-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0b12/10005641/c35a7fd8fb40/molecules-28-02304-g002.jpg

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