Promiscuous enzyme-catalyzed cascade reaction in water: Synthesis of dicoumarol derivatives

Fu, Yajie; Lu, Zeping; Fang, Ke; He, Xinyi; Huang, He; Hu, Yi

doi:10.1016/j.bmcl.2019.03.007

Cited by 22 publications

(12 citation statements)

References 34 publications

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“…Yet, a recent work was published using this type of catalysts. Hu and coworkers reported the use of the enzyme lipase from fungus Rhizomucor miehei (lipase RMIM) as a biocatalyst in the Knoevenagel–Michael cascade reaction of 4-hydroxycoumarin with aromatic, heterocyclic or aliphatic aldehydes to synthesize dicoumarol derivatives in water with excellent yields (81–98%) (Scheme 9 ) [ 80 ]. The mild reaction conditions, pure aqueous reaction system, broad substrate scope, recyclability of the catalyst, and operational simplicity make this an environmentally friendly process for dicoumarols’ synthesis.…”

Section: General Characterization Of Dicoumarolmentioning

confidence: 99%

Dicoumarol: from chemistry to antitumor benefits

et al. 2022

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Dicoumarol, a coumarin-like compound, is known for its anticoagulant properties associated with the ability to inhibit vitamin K, being prescribed as a drug for several decades. The pharmaceutical value of dicoumarol turned it into a focus of chemists’ attention, aiming its synthesis and of dicoumarol derivatives, bringing to light new methodologies. In recent years, several other bioactive effects have been claimed for dicoumarol and its derivatives, including anti-inflammatory, antimicrobial, antifungal, and anticancer, although the mechanisms of action underlying them are mostly not disclosed and additional research is needed to unravel them. This review presents a state of the art on the chemistry of dicoumarols, and their potential anticancer characteristics, highlighting the mechanisms of action elucidated so far. In parallel, we draw attention to the lack of in vivo studies and clinical trials to assess the safety and efficacy as drugs for later application.

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Section: General Characterization Of Dicoumarolmentioning

confidence: 99%

Dicoumarol: from chemistry to antitumor benefits

et al. 2022

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“…42 In 2019, Fu et al for the first time reported immobilized lipase RMIM (from Rhizomucor miehei)-catalyzed Knoevenagel-Michael cascade reaction, which was used to generate dicoumarol derivatives (►Scheme 13). 43 The method tolerates the reaction of 4-hydroxycoumarin with various aldehydes (aromatic aldehydes/heterocyclic aldehydes/aliphatic aldehydes) in a pure water with a yield of 81 to 98%. Circular dichroism spectroscopy revealed that the secondary structure of RMIM was changed after five times of repeated use of the enzyme.…”

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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“…Knoevenagel-Michael addition reaction is highly significant in organic chemistry for the formation of C-C bonds and most commonly used for the synthesis of biscoumarins and bisdimedones. In this context, many practical procedures using several catalysts such as HAP/Fe 3 O 4 NPs [41], lipase RMIM enzyme [42], Fe 3 O 4 @ SiO 2 -silylcyclopropyldimethylglyoxime-Ni superparamagnetic NPs [43], Fe 3 O 4 @ SiO 2 @Ni-Zn-Fe LDH [44], Bi(NO 3 ) [46], P4VPy [47], Fe(SD) 3 [48], taurine [49], HY zeolite [50], CuFe 2 O 4 @SiO 2 @PTMS@ Tu@Ni(II) [51] and Fe 3 O 4 @sulfosalicylic acid MNPs [52] have been reported by the researchers for the synthesis of biscoumarins. Moreover, bisdimedone derivatives have been synthesized using several catalysts, viz.…”

Section: Introductionmentioning

confidence: 99%

Black yet green: A heterogenous carbon-based acid catalyst for the synthesis of biscyclic derivatives under eco-friendly conditions

Teli¹,

Sethiya²,

Agarwal³

2021

Res Chem Intermed

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In this study, a simple, cost-efficient and green protocol has been described for the synthesis of biscoumarin and bisdimedone derivatives via one-pot Knoevenagel-Michael reaction of aromatic aldehydes with 4-hydroxycoumarin and dimedone, respectively. This approach has defined a new way of synthesizing products (4a-i and 5a-i) in high yields using carbon sulfonic acid as a heterogeneous solid acid catalyst. All the reactions have been executed in a greener medium in short reaction times with high-to-excellent yields. This organic synthesis adheres to the principles of green chemistry as the catalyst is cheap, gentle toward environment, easy to handle and reusable up to six cycles, easily separable through filtration, green reaction media and high yield of derivatives in short reaction time. The structure of the synthesized compounds was established by spectral analysis.

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Promiscuous enzyme-catalyzed cascade reaction in water: Synthesis of dicoumarol derivatives

Cited by 22 publications

References 34 publications

Dicoumarol: from chemistry to antitumor benefits

Dicoumarol: from chemistry to antitumor benefits

Progress in the Synthesis of Heterocyclic Compounds Catalyzed by Lipases

Black yet green: A heterogenous carbon-based acid catalyst for the synthesis of biscyclic derivatives under eco-friendly conditions

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