Microwave-assisted synthesis of base modified Furo[3,2-c]quinolone nucleosides and insights into their photophysical properties

IF 4.2 3区工程技术 Q2 CHEMISTRY, APPLIED Dyes and Pigments Pub Date : 2025-09-01 Epub Date: 2025-04-12 DOI:10.1016/j.dyepig.2025.112826

Sumit Kumar , Aditi Arora , Gautam Deo , Mrityunjay K. Tiwari , Jyotirmoy Maity , Brajendra K. Singh

引用次数: 0

Abstract

A green, catalyst free, one-pot, gram scale microwave-assisted synthesis of fluorescent furo [3,2-c]quinolone nucleoside analogues has been successfully developed using 2-Me-THF as a greener solvent. This method, employing 3′,5′-di-O-acetyl-5-formyl-2′-deoxyuridine, alkyl isocyanides, and differently substituted 4-hydroxyquinolones, achieved product yield up to 92 %, which offers high atom economy, reduced reaction time and simple work-up procedure. The products were fully characterized by spectroscopic techniques and single crystal X-ray analysis with DFT analysis conforming the electronic structures. Fluorescence studies revealed strong emission (∼450 nm), large Stokes shifts (59–98 nm), and high quantum yields (0.053–0.595). Solvatochromism studies highlighted their environmental sensitivity, indicating potential applications in nucleic acid research and bio-imaging.

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微波辅助合成碱修饰呋喃[3,2-c]喹诺酮类核苷及其光物理性质研究

利用 2-Me-THF 作为绿色溶剂，成功开发了一种绿色、无催化剂、单锅、克级规模的荧光呋喃 [3,2-c]喹诺酮核苷类似物微波辅助合成方法。该方法采用 3′,5′-二-O-乙酰基-5-甲酰基-2′-脱氧尿苷、烷基异氰酸酯和不同取代的 4-羟基喹诺酮，产品收率高达 92%，具有原子经济性高、反应时间短和操作步骤简单等优点。通过光谱技术和单晶 X 射线分析以及符合电子结构的 DFT 分析，对产品进行了全面表征。荧光研究显示了强发射（450 纳米）、大斯托克斯位移（59-98 纳米）和高量子产率（0.053-0.595）。溶解变色研究强调了它们对环境的敏感性，这表明它们在核酸研究和生物成像方面具有潜在的应用价值。

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来源期刊

Dyes and Pigments 工程技术-材料科学：纺织

CiteScore

8.20

自引率

13.30%

发文量

933

审稿时长

33 days

期刊介绍： Dyes and Pigments covers the scientific and technical aspects of the chemistry and physics of dyes, pigments and their intermediates. Emphasis is placed on the properties of the colouring matters themselves rather than on their applications or the system in which they may be applied. Thus the journal accepts research and review papers on the synthesis of dyes, pigments and intermediates, their physical or chemical properties, e.g. spectroscopic, surface, solution or solid state characteristics, the physical aspects of their preparation, e.g. precipitation, nucleation and growth, crystal formation, liquid crystalline characteristics, their photochemical, ecological or biological properties and the relationship between colour and chemical constitution. However, papers are considered which deal with the more fundamental aspects of colourant application and of the interactions of colourants with substrates or media. The journal will interest a wide variety of workers in a range of disciplines whose work involves dyes, pigments and their intermediates, and provides a platform for investigators with common interests but diverse fields of activity such as cosmetics, reprographics, dye and pigment synthesis, medical research, polymers, etc.