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2,3-二氢喹唑啉-4(1H)-酮:可见光介导的合成、溶剂变色和生物活性。

2,3-Dihydroquinazolin-4(1H)-ones: visible light mediated synthesis, solvatochromism and biological activity.

机构信息

Organic Chemistry Division, School of Advanced Sciences, VIT University, Vellore 632 014, Tamil Nadu, India.

Organic Chemistry Division, School of Advanced Sciences, VIT University, Vellore 632 014, Tamil Nadu, India.

出版信息

J Photochem Photobiol B. 2015 Feb;143:139-47. doi: 10.1016/j.jphotobiol.2014.12.028. Epub 2015 Jan 13.

DOI:10.1016/j.jphotobiol.2014.12.028
PMID:25625562
Abstract

The photochemical synthesis of a series of 2,3-dihydroquinazolin-4(1H)-ones were evaluated under the irradiation of visible light (>390nm). The effect of the visible light mediated synthesis was carried out in the presence/absence of solvent. The effect of solvent plays a key role in the synthesis was evidenced through the formation of product in short duration. The solvatochromic effects of the fluorescent compounds (3a-k) were studied with respect to the solvents of increasing polarity (DCM<methanol<DMF<DMSO). The determination of in vitro anti-inflammatory activity of the compounds (3a-k) by the inhibition of bovine serum albumin (BSA) denaturation and 2,2-di(4-t-octylphenyl)-1-picrylhydrazyl (DOPPH) radical scavenging consequence of the compounds (3a-k) were determined by spectroscopic technique. The compound 3j in DMSO exhibited extreme high quantum yield. The compound 3i was found to be superior both in the efficiency of the anti-inflammatory activity and radical scavenging ability.

摘要

可见光(>390nm)照射下,评价了一系列 2,3-二氢喹唑啉-4(1H)-酮的光化学合成。在有无溶剂的情况下进行了可见光介导的合成效果。溶剂的作用对合成有显著影响,通过在短时间内形成产物得到证明。研究了荧光化合物(3a-k)的溶剂化效应与极性增加的溶剂(DCM<甲醇<DMF<DMSO)之间的关系。通过抑制牛血清白蛋白(BSA)变性和化合物(3a-k)清除 2,2-二(4-叔辛基苯基)-1-吡咯基氢过氧化物(DOPPH)自由基,用光谱技术测定了化合物(3a-k)的体外抗炎活性。在 DMSO 中,化合物 3j 表现出极高的量子产率。发现化合物 3i 在抗炎活性和自由基清除能力方面都具有优势。

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