Solution-phase Synthesis of a Combinatorial Library of 3-[4-(Coumarin-3-yl)-1,3-thiazol-2-ylcarbamoyl]propanoic acid Amides

Abstract

The parallel solution-phase synthesis of a new combinatorial library of 3-[4-(R1-coumarin-3-yl)-1,3-thiazol-2-ylcarbamoyl]propanoic acid amides 9 has been developed. The synthesis involves two steps: 1) the synthesis of core building blocks – 3- [4-(coumarin-3-yl)-1,3-thiazol-2-ylcarbamoyl]propanoic acids, 6 – by the reaction of 3-(ω-bromacetyl)coumarins 1 with 3-amino(thioxo)methylcarbamoylpropanoic acid (5); 2) the synthesis of the corresponding 3-[4-(coumarin-3-yl)-1,3-thiazol-2-yl- carbamoyl]propanoic acids amides 9 using 1,1’-carbonyldimidazole as a coupling reagent. The advantages of the method compared to existing ones are discussed.

Synthesis and biological evaluation of novel conjugated coumarin‐thiazole systems

“…In the last few years, researchers have renewed interest in 3‐(thiazol‐4‐yl)coumarins [1–6] for their industrial applications as fluorescent probes and laser dyes [7], for their biological activity as pharmaceutical agents [8–10] and because they could be useful for the construction of the diazepinone ring [11]. In addition, π‐conjugated systems are known to show interesting electronic, optical, and electric properties [12].…”

Synthesis, Reactions and Antimicrobial Activities of 8-Ethoxycoumarin Derivatives

“…Treatment of 3-ethoxysalicylaldehyde ( 1 ) with ethyl acetoacetate ( 2 ) in boiling ethanol containing few drops of piperidine afforded 3-acetyl-8-ethoxycoumarin ( 3 ) [ 29 ]. Bromination of 3 in acetic acidgave the corresponding ω -bromo-8-ethoxy-3-acetylcoumarin ( 4 ) [ 29 ] ( Scheme 1 ).…”

“…130–132 °C, lit. (135–7 °C) [ 29 ]; IR (KBr) υ (cm −1 ): 3,060, 2,976, 2,874 (CH stretching), 1,730, 1,678 (CO); 1 H-NMR (DMSO-d 6 ) δ: 1.40 (t, 3H, CH 3 , J = 7.2 Hz), 2.58 (s, 3H, COCH 3 ), 4.19 (q, 2H, CH 2 , J = 7.2 Hz), 7.31-7.65 (m, 3H, Ar-H), 8.59 (s, 1H, H-4); 13 C-NMR (DMSO-d 6 ) δ: 13.90 (CH 3 -ester), 25.72 (CH 3 -acetyl), 62.33 (CH 2 -ester), 115.40 (C-7), 118.21 (C-5), 120.11 (C-4a), 126.37 (C-6), 128.00 (C-3), 145.03 (C-4), 150.80 (C-8a), 154.12 (C-8), 160.04 (CO-lactone), 175.19 (CO-acetyl); Anal. calcd.…”

Synthesis and Biological Evaluation of Novel Thiazolyl-Coumarin Derivatives as Potent Histone Deacetylase Inhibitors with Antifibrotic Activity

“…The solution was allowed to cool to room temperature, filtered and the precipitate washed with three 10 mL portions of cold ethanol. All brominated derivatives were recrystallized from an 80:20 ethanol/chloroform mixture and characterized by their melting points, 1 H-NMR, 13 C-NMR, and FTIR [ 56 , 57 ].…”