Promiscuous enzyme-catalyzed cascade reaction: Synthesis of xanthone derivatives

Fu, Yajie; Fan, Bing-Bing; Chen, Hongyue; Huang, He; Hu, Yi

doi:10.1016/j.bioorg.2018.06.034

Cited by 25 publications

(11 citation statements)

References 27 publications

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“…38,39 In 2018, our research group discovered a novel method for the synthesis of xanthones: lipase TLIM-catalyzed Knoevenagel-Michael cascade reactions of 1,3-diketones with aromatic aldehydes/heterocyclic aldehydes/aliphatic aldehydes in n-hexane (►Scheme 12). 40 The yield can be up to 80 to 97%. Target products of this reaction were usually ring-opened xanthone compounds, yet, ring-closed xanthones were formed when pyridine-2-carboxaldehyde/2,6-dichlorobenzaldehyde reacted with 1,3-cyclohexanedione under a high temperature or strong acid.…”

Section: Synthesis Of Six-membered Heterocyclic Compounds Containing Oxygenmentioning

confidence: 99%

Progress in the Synthesis of Heterocyclic Compounds Catalyzed by Lipases

Wang

Shen

et al. 2021

Pharmaceutical Fronts

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Heterocyclic compounds are representative of a larger class of organic compounds, and worthy of attention for many reasons, chief of which is the participation of heterocyclic scaffolds in the skeleton structure of many drugs. Lipases are enzymes with catalytic versatility, and play a key role in catalyzing the reaction of carbon–carbon bond formation, allowing the production of different compounds. This article reviewed the lipase-catalyzed aldol reaction, Knoevenagel reaction, Michael reaction, Mannich reaction, etc., in the synthesis of several classes of heterocyclic compounds with important physiological and pharmacological activities, and also prospected the research focus in lipase-catalyzed chemistry transformations in the future.

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Section: Synthesis Of Six-membered Heterocyclic Compounds Containing Oxygenmentioning

confidence: 99%

Progress in the Synthesis of Heterocyclic Compounds Catalyzed by Lipases

Wang

Shen

et al. 2021

Pharmaceutical Fronts

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“…Enzymes play an important catalytic role in various C -C bond forming, Mannich reaction, Henry reaction, Knoevenagel condensation, Michael addition, and BaylisÀ Hillman reactions, among others. In this sense, Fu et al [160] have reported the use of immobilized lipase TLIM as catalyst in the KnoevenagelÀ Michael cascade reactions of 1,3-diketones with aromatic aldehydes to synthesize xanthone derivatives. This provides several advantages, such as environmental appeal, simple work-up, excellent yields and potential for biocatalyst recycling.…”

Section: Synthetic Routesmentioning

confidence: 99%

Xanthones and Cancer: from Natural Sources to Mechanisms of Action

Klein‐Júnior

Campos

Niero

et al. 2020

Chemistry & Biodiversity

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Xanthones are a class of heterocyclic natural products that have been widely studied for their pharmacological potential. In fact, they have been serving as scaffolds for the design of derivatives focusing on drug development. One of the main study targets of xanthones is their anticancer activity. Several compounds belonging to this class have already demonstrated cytotoxic and antitumor effects, making it a promising group for further exploration. This review therefore focuses on recently published studies, emphasizing their natural and synthetic sources and describing the main mechanisms of action responsible for the anticancer effect of promising xanthones.

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“…Exploiting enzyme catalytic promiscuity can afford new synthesis pathways and lead to improvements in existing catalysts [2]. Lipases are the most frequently used enzymes in this area and bring about a range of promiscuous reactions, such as Michael addition, Knoevenagel reaction, Aldol addition, Morita–Baylis–Hillman reaction, perhydrolysis, and some cascade reactions [3‐13]. However, most of these reported enzyme promiscuous reactions suffer from various drawbacks such as poor stabilities of enzymes and difficulties in recovery and recycling for enzymes under nonnatural conditions.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of substituted 2H‐chromenes catalyzed by lipase immobilized on magnetic multiwalled carbon nanotubes

Liu

Zhao

Zhang

et al. 2020

Biotech and App Biochem

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Porcine pancreas lipase (PPL) was immobilized on magnetic multiwalled carbon nanotubes successfully for the synthesis of substituted 2H‐chromenes. The catalytic activity of immobilized PPL was much higher than that of free PPL. Effects of reaction medium, temperature, and enzyme dosage were also investigated. Under optimum reaction conditions (acetylacetone (1 mmol), salicylaldehyde (1 equivalent), methanol (10 equivalent), and immobilized PPL (protein content: 30 mg; 65 °C; DMF 5 mL; 5 H), the immobilized PPL showed an excellent catalytic performance on the synthesis of substituted 2H‐chromenes. Moreover, the immobilized PPL exhibited satisfactory thermostability, operational simplicity, and reusability in this reaction.

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Promiscuous enzyme-catalyzed cascade reaction: Synthesis of xanthone derivatives

Cited by 25 publications

References 27 publications

Progress in the Synthesis of Heterocyclic Compounds Catalyzed by Lipases

Progress in the Synthesis of Heterocyclic Compounds Catalyzed by Lipases

Xanthones and Cancer: from Natural Sources to Mechanisms of Action

Synthesis of substituted 2H‐chromenes catalyzed by lipase immobilized on magnetic multiwalled carbon nanotubes

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