Design and synthesis of a novel colorimetric fluorescent probe for the selective detection of sulfur dioxide in SH-SY5Y neuroblastoma cells and its applications in traditional Chinese medicines

Abstract

A fast response time, low limit of detection and high fluorescence quantum yield probe DTCC was designed and synthesized to detect SO2 derivatives based on coumarin-thiophene dye which was fused with a coumarin moiety and 2-thiophenecarboxaldehyde.

l-Proline-Catalyzed Three-Component Reaction of 4-Chloro-3-formylcoumarin, Sodium Sulfide, and α-Halo Ketones: A Direct Approach to Thieno[3,2-c]coumarins

“…42 Thieno[3,2-c]coumarins have also been prepared by the reaction of 4-chloro-3-formylcoumarin with a thioglycolate and 1,4-dithiane-2,5-diol or a combination of sodium sulfide and chloroacetaldehyde. [43][44][45][46][47][48] In following the second approach (the construction of the pyrone), the palladium-catalyzed carbonylation of 2-(3-thienyl)phenol leads to the formation of thieno[3,2-c]coumarins. 49,50 The target coumarins have also been prepared by the cyclization of alkyl (2-methoxy)aryl-2-thienylcarboxylates and -3thienylcarboxylates in the presence of BBr 3 and t-BuOK.…”

“…The reaction of 4-chloro-3-formylcoumarin (1) with a sulfide source and phenacyl bromide (4a) was selected as a model reaction (Table 1). Inspired by an earlier work, 48 we combined 4-chloro-3-formylcoumarin (1; 1.0 mmol) with Na 2 S•9H 2 O (1.0 mmol) in DMF and then stirred the mixture at 60 °C for two hours with subsequent addition of phenacyl bromide (4a; 1.1 mmol) and K 2 CO 3 (1.1 mmol). After a further two hours of stirring at 60 °C, the reaction was quenched and the crude product was purified by column chromatography, giving the desired product 5a in 23% yield, together with a considerable amount of an uncharacterized white solid, with no involvement of phenacyl bromide (Table 1, entry 1).…”

From Blue to Green Photoluminescence: Design, Synthesis, and DFT Calculations of Heterocyclic Compounds Containing Chromenothienopyrimidine Moiety

“…[18] Thiophene-fused coumarins, such as thieno [3,2c]coumarin, have also been utilized in medicinal chemistry and materials science. Some thieno[3,2-c]coumarins, for example, have antibacterial, [19] anti-inflammatory, [20] cytostatic activity, [21] and fluorescent probes for the selective detection of sulfur dioxide [22] and hypochlorite anion. [23] It was discovered that merging coumarin and pyrimidine nuclei may significantly enhance both the biological photophysical properties of these hybrid structures, maximizing their potential applications.…”