Synthesis, Molecular Engineering, and Photophysical Properties of Fluorescent Thieno[3,2-b]pyridine-5(4H)-ones

Abstract

We describe a synthetic approach for a set of fluorescent thieno­[3,2-b]­pyridine-5­(4H)-one derivatives and their photophysical properties. These fluorophores are prepared by a series of reactions employing the Suzuki–Miyaura cross-coupling reaction and a regioselective aza-[3 + 3] cycloaddition of 3-aminothiophenes with α,β-unsaturated carboxylic acids. Our findings revealed that the photophysical properties are chemically tunable by an appropriate choice of functional group on the thieno­[3,2-b]­pyridine-5­(4H)-one scaffold.

Development of Human Serum Albumin Selective Fluorescent Probe Using Thieno[3,2-b]pyridine-5(4H)-one Fluorophore Derivatives

“…General synthetic procedure for KF derivatives can be found in our previous report [38]. The detailed synthetic procedures of KF 1 – 12 were previously reported and that of KF 13 and KF 14 were described in Supplementary Material.…”

“…To develop a novel fluorescent probe having high sensitivity and selectivity for HSA, we utilized the fluorescence-based, high-throughput screening of a set of novel fluorophore derivatives against plasma proteins (Scheme 1). Recently, we have reported novel fluorophore scaffolds: thieno[3,2- b ]pyridine-5( 4H )-one derivatives [hereafter, collectively referred to as KIOST-Fluor (KF)], synthesized via a series of reactions including the Suzuki-Miyaura cross-coupling reaction and a regioselective aza-[3+3] cycloaddition of 3-aminothiophenes with α,β-unsaturated carboxylic acids [38]. By varying the functional group on the KF scaffold, the fluorophore showed different photophysical properties; in particular, they exhibited remarkable environmental sensitivities.…”

A Fluorescent Probe for Selective Facile Detection of H2S in Serum Based on an Albumin-Binding Fluorophore and Effective Masking Reagent

“…The key intermediate compound 5a was synthesized according to the modified method from the previously reported methods. 45 Synthesis of Methyl 5-(4-(Diethylamino)phenyl)-3-(methylamino)thiophene-2-carboxylate (3a). To a solution of 2a (1.04 g, 4.14 mmol, 1.0 equiv.)…”

“…1 H NMR (600 MHz, CDCl 3 ) δ 7.50 (d, J = 9.0 Hz, 2H), 6.70 (s, 1H), 6.65 (d, J = 9.0 Hz, 2H), 3.81 (s, 3H), 3.33 (q, J = 7.0 Hz, 4H), 3.02 (d, J = 4.8 Hz, 3H), 1.19 (t, J = 7.2 Hz, 6H); 13 C{ 1 H} NMR (150 MHz, CDCl 3 ) δ 165.3, 158.0, 151.4, 148.3, 127.3, 120.5, 111.4, 108.7, 94.9, 50.9, 44.4, 31.6, 12.6; Data are consistent with those reported in the literature. 45 Synthesis of 6-Bromo-2-(4-(diethylamino)phenyl)-7-(4methoxyphenyl)-4-methylthieno[3,2-b]pyridin-5(4H)-one (7a). To a solution of 5a (150 mg, 0.5760 mmol, 1.0 equiv.)…”

Domino Synthetic Strategy for Tetrahydrothiopyran Derivatives from Benzaldehydes, 2-Acetylfuran/2-Acetylthiophene, and Sodium Sulfide

“…Sulfur-containing compounds are widely applied as pesticides, medicines, and synthons playing irreplaceable roles in academic and industrial communities. − Tetrahydrothiopyran (THTP) derivatives have been testified to exhibit many pharmaceutical properties such as antibacterial, anticancer, anti-inflammatory, and antiviral activities. − In the past decades, some convenient methods for the synthesis of THTP derivatives have been developed. However, most of them suffer from a number of drawbacks such as the introduction of expensive or toxic metal catalysts, long synthesis routes, limited substrate scopes, and low yields. − These problems greatly limited their practical application.…”