Evaluation of Biodegradable Glucose Based Surfactants as a Promoting Medium for the Synthesis of Peptidomimetics with the Coumarin Scaffold

Abstract

6‐O‐Glucose‐4‐phenylbutyrate was used successfully as promoting aqueous reaction medium for the synthesis of fourteen different α‐acyloxy carboxamides with the biologically relevant coumarin scaffold. Two different one‐pot protocols; chemical and chemoenzymatic, based on the usage of biodegradable surfactants for the synthesis of target products were developed. The chemoenzymatic method consists of 3‐steps in which the first step is oxidation catalyzed by Trametes versicolor laccase/O2, followed by spontaneous condensation reaction, and finally multicomponent Passerini reaction. All transformations occurred at room temperature in the same reaction vials without isolation of the reaction intermediates. The influence of the reaction conditions including substrate structure on the reaction course was studied. The application of an aqueous solution of 6‐O‐glucose 4‐phenylbutyrate as the reaction medium had the pivotal impact of the reaction rate providing target α‐acyloxy carboxamides with the yields up to 65 %. Obtained peptidomimetics were characterized by UV‐VIS and fluorescence spectroscopy.

Pyridine Derivatives—A New Class of Compounds That Are Toxic to E. coli K12, R2–R4 Strains

“…), and thiols in the presence of a catalyst [ 17 , 18 ]. Various catalysts have been reported to effect MCR, including nano-crystalline magnesium oxide, [ 19 ] silica nanoparticles [ 20 ], ZnCl 2 [ 21 ], piperidine/microwave [ 22 ] and Cd(II) metal–organic frameworks [ 23 ], refluxed in basic alumina [ 24 ]. Although the reported methods are efficient to provide the desired 2-amino-4-aryl-3,5-dicarbonitrile-6-sulfanylpyridines, there are still some drawbacks regarding these protocols, such as their longer reaction time, limited substrate scope, and complicated work-up processes, as well as the application of expensive, highly toxic and carcinogenic transition metal catalysts.…”

“…All bacterial strains were received and statistically analysed, as described in [ 5 , 6 , 7 , 8 , 9 , 10 , 11 , 12 , 13 , 14 , 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 , 37 , 38 , 39 , 40 , 41 , 42 , 43 , 44 , 45 , 46 , 47 , 48 , 49 , 50 , 51 , 52 , 53 , 54 , 55 ].…”

Multicomponent synthesis of chromophores – The one-pot approach to functional π-systems

“…The three steps of the sequence starting from salicylic alcohol derivatives include a Trametes versicolor laccase catalyzed aerobical oxidation, aldol condensation and 6-O-glucose ester promoted Passerini MCR. By modification of alcohols, aldehydes, or isocyanides, α-acyloxy carboxamides containing a coumarin scaffold 44 are obtained in variable yields (Scheme 12A) (Paprocki et al, 2020). The synthesis can also be started with the third step employing coumarin-3carboxylic acids as starting materials in the terminal Passerini reaction.…”

“…Components 50 also possess anticancer activity. SCHEME 12 (A) Three-step one-pot synthesis of α-acyloxy carboxamides 44 (Paprocki et al, 2020). (B) Biginelli reaction to synthesize 3,4-dihydropyrimidin-2(1H)-one/thiones 47 in the sense of the scaffold concept (Vitório et al, 2015).…”