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新型取代色烯并[4,3-c]吡唑-4-酮的合成及其抗氧化活性。

Synthesis of new substituted chromen[4,3-c]pyrazol-4-ones and their antioxidant activities.

机构信息

College of Science and Arts at Ar-Rass, Qassim University, P.O. Box 53, Saudi Arabia.

出版信息

Molecules. 2011 Dec 12;16(12):10292-302. doi: 10.3390/molecules161210292.

DOI:10.3390/molecules161210292
PMID:22158652
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6264664/
Abstract

A series of new coumarin derivatives 4 containing a 4-arylbut-3-en-2-one moiety were synthesized by condensation of 3-acetylcoumarin 1 with aryl aldehydes 2 in chloroform in the presence of piperidine. The interactions of 3-formyl-4-chlorocoumarin (3) with nitrogen-containg nucleophiles leading to the corresponding substituted chromen-[4,3-c]pyrazol-4-ones 5 are described. The structures of the obtained compounds were established on the basis of 1D NMR, 2D NMR and IR and further the compounds were evaluated for possible antioxidant activities. The coumarinic chalcone 4a has been found to be the most active (IC₅₀ = 2.07 μM) in this study.

摘要

一系列含有 4-芳基丁-3-烯-2-酮部分的新型香豆素衍生物 4 通过 3-乙酰基香豆素 1 与氯仿中的芳醛 2 在哌啶存在下缩合合成。描述了 3-甲酰基-4-氯香豆素(3)与含氮亲核试剂的相互作用,导致相应取代的色烯-[4,3-c]吡唑-4-酮 5。根据 1D NMR、2D NMR 和 IR,确定了所得化合物的结构,并进一步评估了它们可能的抗氧化活性。在这项研究中,香豆素查耳酮 4a 被发现是最活跃的(IC₅₀ = 2.07 μM)。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e748/6264664/ce2ccdf75aac/molecules-16-10292-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e748/6264664/2d42133c957f/molecules-16-10292-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e748/6264664/1bcd10983c7f/molecules-16-10292-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e748/6264664/9f812cb2c00b/molecules-16-10292-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e748/6264664/bf359bddc412/molecules-16-10292-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e748/6264664/ce2ccdf75aac/molecules-16-10292-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e748/6264664/2d42133c957f/molecules-16-10292-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e748/6264664/1bcd10983c7f/molecules-16-10292-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e748/6264664/9f812cb2c00b/molecules-16-10292-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e748/6264664/bf359bddc412/molecules-16-10292-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e748/6264664/ce2ccdf75aac/molecules-16-10292-g005.jpg

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