Lipase‐Catalyzed Synthesis of Anthrone Functionalized Benzylic Amines via a Multicomponent Reaction in Supercritical Carbon Dioxide

Li, Fengxi; Wang, Ciduo; Xu, Yaning; Gao, Xiaojun; Xu, Yuelin; Xie, Hanqing; Chen, Peng; Wang, Lei

doi:10.1002/slct.202104517

Cited by 5 publications

(5 citation statements)

References 47 publications

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“…Therefore, the possibility of using the biocatalytic approach in the synthesis of target β-phosphonates should be considered. The use of hydrolases as catalysts in various variants of the Michael addition of different nucleophilic partners has been widely discussed in the literature [ 44 , 45 , 46 ]. Recently, it was also shown that lipases catalyze aldol and Knoevenagel condensations [ 47 ].…”

Section: Resultsmentioning

confidence: 99%

Promiscuous Lipase-Catalyzed Knoevenagel–Phospha–Michael Reaction for the Synthesis of Antimicrobial β-Phosphono Malonates

Samsonowicz-Górski

Koszelewski

Kowalczyk

et al. 2022

IJMS

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An enzymatic route for phosphorous–carbon bond formation was developed by discovering new promiscuous activity of lipase. We reported a new metal-free biocatalytic method for the synthesis of pharmacologically relevant β-phosphonomalononitriles via a lipase-catalyzed one-pot Knoevenagel–phospha–Michael reaction. We carefully analyzed the best conditions for the given reaction: the type of enzyme, temperature, and type of solvent. A series of target compounds was synthesized, with yields ranging from 43% to 93% by enzymatic reaction with Candida cylindracea (CcL) lipase as recyclable and, a few times, reusable catalyst. The advantages of this protocol are excellent yields, mild reaction conditions, low costs, and sustainability. The applicability of the same catalyst in the synthesis of β-phosphononitriles is also described. Further, the obtained compounds were validated as new potential antimicrobial agents with characteristic E. coli bacterial strains. The pivotal role of such a group of phosphonate derivatives on inhibitory activity against selected pathogenic E. coli strains was revealed. The observed results are especially important in the case of the increasing resistance of bacteria to various drugs and antibiotics. The impact of the β-phosphono malonate chemical structure on antimicrobial activity was demonstrated. The crucial role of the substituents attached to the aromatic ring on the inhibitory action against selected pathogenic E. coli strains was revealed. Among tested compounds, four β-phosphonate derivatives showed an antimicrobial activity profile similar to that obtained with currently used antibiotics such as ciprofloxacin, bleomycin, and cloxacillin. In addition, the obtained compounds constitute a convenient platform for further chemical functionalization, allowing for a convenient change in their biological activity profile. It should also be noted that the cost of the compounds obtained is low, which may be an attractive alternative to the currently used antimicrobial agents. The observed results are especially important because of the increasing resistance of bacteria to various drugs and antibiotics.

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Section: Resultsmentioning

confidence: 99%

Promiscuous Lipase-Catalyzed Knoevenagel–Phospha–Michael Reaction for the Synthesis of Antimicrobial β-Phosphono Malonates

Samsonowicz-Górski

Koszelewski

Kowalczyk

et al. 2022

IJMS

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“…Lipases have successfully catalyzed chemical reactions such as the Michael addition [27], Knoevenagel reaction [28], Aldol reaction [29], Mannich reaction [30], and oxidation reactions [31]. Our group conducted a number of studies on lipase-catalyzed unnatural reactions in various solvents, including organic solvents [32], ionic liquids [33], and supercritical carbon dioxide [34]. The results fully illustrated the feasibility and strong potential of lipase-catalyzed organic synthesis.…”

Section: Effect Of Lipase Sourcementioning

confidence: 88%

Efficient Synthesis of Pyrrole Disulfides Catalyzed by Lipase in Ethanol

Wen,

Xu,

et al. 2023

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Disulfides, as fundamental scaffolds, are widely present in peptides, natural products, and pharmaceutical molecules. However, traditional synthesis of disulfides often involves the utilization of toxic reagents or environmentally unfriendly reaction conditions. In this work, a green and efficient method was developed for synthesizing pyrrole disulfides using β-ketothioamides and ethyl cyanoacetate as substrates, with lipase serving as a catalyst. Under the optimal conditions (β-Ketothioamides (1 mmol), ethyl cyanoacetate (1 mmol), PPL (200 U), and EtOH (5 mL)), lipase leads to the formation of pyrrole disulfides in yields of up to 88% at 40 °C. The related mechanism is also speculated in this paper. This approach not only presents a new application of lipase in enzyme catalytic promiscuity, but also offers a significant advancement in the synthetic pathway for pyrrole disulfides and aligns with the current mainstream research direction of green chemistry, contributing to the further development of environmentally friendly biocatalytic processes.

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“…[1] It is a very powerful tool to produce highly and diverse structures in one step and mostly over a short reaction time, that save energy and cost. [2][3][4][5] The synthesis of 1,8-Dioxohexahydroacridine is the noteworthy sample of these MCRs. Acridine derivatives are one of the most important and attractive classes of bioactive compounds that have occupied a unique position in medicinal chemistry.…”

Section: Introductionmentioning

confidence: 99%

“…In recent years, multicomponent reactions (MCRs), have gained remarkable interest to access complex structurally diverse bioactive heterocyclic compounds [1] . It is a very powerful tool to produce highly and diverse structures in one step and mostly over a short reaction time, that save energy and cost [2–5] …”

Section: Introductionmentioning

confidence: 99%

Preparation of Core/Shell Fe₃O₄@SiO₂ ⋅ DIL as a Magnetically Separable Catalyst for the Synthesis of 1, 8‐Dioxodecahydroacridine

Ebadi,

Vadie,

Shojaei

2024

ChemistrySelect

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In this research, design and synthesis of the magnetic nanoparticle, coated by a silica shell and modified with dicationic ionic liquid are described. The characterization of Fe3O4@SiO2 ⋅ DIL was done by means of techniques such as XRD, FTIR, SEM, EDX, TEM, and TGA. The catalytic activity of Fe3O4@SiO2 ⋅ DIL as a new nanocatalyst was tested in the one‐pot tree‐component synthesis of 1,8‐dioxodecahydroacridines. To achieve higher yield of products, factors such as reaction temperature, reaction time, the amount of nanocatalyst and solvent were studied, and the optimized conditions were investigated. The results indicated that the reaction time for aromatic aldehydes bearing substituent at para position is shorter and higher yields of products were obtained with these substrates. Short reaction time, high yield of products, easy purification and easy recoverable catalyst without significantly loss of its activity are the main advantages of the process presented. The results clearly showed that the existing catalytic system could be eco‐friendly and economical to carry out this reaction.

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Lipase‐Catalyzed Synthesis of Anthrone Functionalized Benzylic Amines via a Multicomponent Reaction in Supercritical Carbon Dioxide

Cited by 5 publications

References 47 publications

Promiscuous Lipase-Catalyzed Knoevenagel–Phospha–Michael Reaction for the Synthesis of Antimicrobial β-Phosphono Malonates

Promiscuous Lipase-Catalyzed Knoevenagel–Phospha–Michael Reaction for the Synthesis of Antimicrobial β-Phosphono Malonates

Efficient Synthesis of Pyrrole Disulfides Catalyzed by Lipase in Ethanol

Preparation of Core/Shell Fe₃O₄@SiO₂ ⋅ DIL as a Magnetically Separable Catalyst for the Synthesis of 1, 8‐Dioxodecahydroacridine

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Lipase‐Catalyzed Synthesis of Anthrone Functionalized Benzylic Amines via a Multicomponent Reaction in Supercritical Carbon Dioxide

Cited by 5 publications

References 47 publications

Promiscuous Lipase-Catalyzed Knoevenagel–Phospha–Michael Reaction for the Synthesis of Antimicrobial β-Phosphono Malonates

Promiscuous Lipase-Catalyzed Knoevenagel–Phospha–Michael Reaction for the Synthesis of Antimicrobial β-Phosphono Malonates

Efficient Synthesis of Pyrrole Disulfides Catalyzed by Lipase in Ethanol

Preparation of Core/Shell Fe3O4@SiO2 ⋅ DIL as a Magnetically Separable Catalyst for the Synthesis of 1, 8‐Dioxodecahydroacridine

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Preparation of Core/Shell Fe₃O₄@SiO₂ ⋅ DIL as a Magnetically Separable Catalyst for the Synthesis of 1, 8‐Dioxodecahydroacridine