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一种高效、无催化剂且以乙醇水溶液介导的5-((2-氨基噻唑-5-基)(苯基)甲基)-6-羟基嘧啶-2,4(1,3)-二酮衍生物的合成及其抗氧化活性。

An efficient, catalyst-free and aqueous ethanol-mediated synthesis of 5-((2-aminothiazol-5-yl)(phenyl)methyl)-6-hydroxypyrimidine-2,4(1,3)-dione derivatives and their antioxidant activity.

作者信息

Patel Paras J, Patel Subham G, Upadhyay Dipti B, Ravi Logeswari, Dhanasekaran Anuradha, Patel Hitendra M

机构信息

Department of Chemistry, Sardar Patel University, Vallabh Vidyanagar 388120 Gujarat India

Centre for Biotechnology, Anna University Chennai Tamil Nadu India.

出版信息

RSC Adv. 2023 Aug 16;13(35):24466-24473. doi: 10.1039/d3ra03998f. eCollection 2023 Aug 11.

DOI:10.1039/d3ra03998f
PMID:37593670
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10427891/
Abstract

In this study, we effectively developed a catalyst-free multicomponent synthesis of 5-((2-aminothiazol-5-yl)(phenyl)methyl)-6-hydroxypyrimidine-2,4(1,3)-dione derivatives employing 2-aminothiazole, ','-dimethyl barbituric acid/barbituric acid and different aldehydes at 80 °C in an aqueous ethanol medium (1 : 1) using group-assisted purification (GAP) chemistry. The essential characteristics of this methodology include superior green credential parameters, metal-free multicomponent synthesis, faster reaction times, greater product yields, simple product purification without column chromatography and higher product yields. All of the synthesized compounds were analyzed against the HepG2 cell line. Compounds 4j and 4k shows good anti-proliferative effects on HepG2 cells. Furthermore, the ABTS and DPPH scavenging assays were used to determine the antioxidant activity of all compounds (4a-r). In both ABTS and DPPH radical scavenging assays, compounds 4e, 4i, 4j, 4o and 4r exhibit excellent potency compared to the standard ascorbic acid.

摘要

在本研究中,我们利用基团辅助纯化(GAP)化学方法,在80℃的乙醇水溶液(1∶1)介质中,以2-氨基噻唑、','-二甲基巴比妥酸/巴比妥酸和不同醛为原料,有效地开发了一种无催化剂的多组分合成5-((2-氨基噻唑-5-基)(苯基)甲基)-6-羟基嘧啶-2,4(1,3)-二酮衍生物的方法。该方法的主要特点包括卓越的绿色化学参数、无金属多组分合成、更快的反应时间、更高的产物收率、无需柱色谱的简单产物纯化以及更高的产物收率。对所有合成化合物针对肝癌细胞系(HepG2)进行了分析。化合物4j和4k对HepG2细胞显示出良好的抗增殖作用。此外,采用ABTS和DPPH清除试验来测定所有化合物(4a - r)的抗氧化活性。在ABTS和DPPH自由基清除试验中,与标准抗坏血酸相比,化合物4e、4i、4j、4o和4r表现出优异的活性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fbc6/10427891/37ceb3b021a6/d3ra03998f-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fbc6/10427891/93158da87ef6/d3ra03998f-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fbc6/10427891/c72ec6a1c537/d3ra03998f-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fbc6/10427891/37ceb3b021a6/d3ra03998f-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fbc6/10427891/93158da87ef6/d3ra03998f-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fbc6/10427891/c72ec6a1c537/d3ra03998f-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fbc6/10427891/37ceb3b021a6/d3ra03998f-f2.jpg

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