Efficient synthesis and antioxidant activities of N-heterocyclyl substituted Coenzyme Q analogues

Wang, Jin; Xia, Fei; Jin, Wenbin; Guan, Jin-Yan; Zhao, Hang

doi:10.1016/j.bioorg.2016.08.008

Cited by 9 publications

(9 citation statements)

References 34 publications

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“…The results (Table 3 ) showed that all the derivatives ( 1 – 19 ) presented higher IC 50 than eugenol, that is, the structural modifications resulted in substances with lower antioxidant effects. All derivatives ( 1 – 11, 13, 15, 17, 20 and 21 ) produced by the esterification reaction on the hydroxyl group showed a strong reduction in antioxidant activity, as expected [ 27 , 37 , 38 ].…”

Section: Resultssupporting

confidence: 71%

Eugenol derivatives: synthesis, characterization, and evaluation of antibacterial and antioxidant activities

Silva

Monte

Lemos

et al. 2018

Chemistry Central Journal

104

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Eugenol is the major component of clove essential oil and has demonstrated relevant biological potential with well-known antimicrobial and antioxidant action. Therefore, this work carried out the synthesis, purification, characterization, and evaluation of the antioxidant and antibacterial potential of 19 eugenol derivatives. The derivatives were produced by esterification reactions in the hydroxyl group (−OH) of eugenol with different carboxylic acids and also by addition reactions in the double bond of the allyl group. The derivatives had a promising antibacterial potential, including a lower minimum inhibitory concentration of 500 μg/mL than eugenol (1000 μg/mL). In addition, the derivatives were active against bacterial strains (Escherichia coli, Staphylococcus aureus) that eugenol itself showed no activity, thus increasing the spectrum of antibacterial action. As for the antioxidant activity, it was observed that the derivatives that involved esterification reactions in the hydroxyl group (−OH) of the eugenol molecule’s phenol resulted in a significant reduction of the antioxidant action (IC50 > 100 μg/mL) when compared with the eugenol precursor molecule (IC50 = 4.38 μg/mL). On the other hand, the structural changes located in the double bond affected much more smoothly the capacity of capturing radicals than the starting molecule, also being obtained derivatives with proximal antioxidant capacity (IC50 = 19.30 μg/mL) to commercial standards such as Trolox (IC50 = 16.00 μg/mL).Electronic supplementary materialThe online version of this article (10.1186/s13065-018-0407-4) contains supplementary material, which is available to authorized users.

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Section: Resultssupporting

confidence: 71%

Eugenol derivatives: synthesis, characterization, and evaluation of antibacterial and antioxidant activities

Silva

Monte

Lemos

et al. 2018

Chemistry Central Journal

104

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“…The protonation of piperazine is employed as a simple way of protection of the secondary nitrogen atom resulting in the suppression of a competitive reaction leading to disubstituted derivatives. Although the principle of a protonated piperazine was rarely mentioned in literature [26][27][28]32], it was not applied in a broader scale for the synthesis of other monosubstituted piperazines. Nonetheless, our long-time research has shown that the principle is applicable to the synthesis of a wide range of monosubstituted piperazines.…”

Section: One-step Synthesis Of Monosubstituted Piperazine Derivativesmentioning

confidence: 99%

“…In case of some benzyl-and substituted benzyl derivatives, especially fluorinated, above-mentioned issues were suppressed and monosubstituted products were obtained in very high yields [20,[26][27][28][29][30][31][32]. However, the same reaction scheme does not usually work sufficiently well in the case of other substituted benzyl derivatives (yields are usually significantly decreased).…”

Section: Introductionmentioning

confidence: 99%

Simplified Procedure for General Synthesis of Monosubstituted Piperazines—From a Batch Reaction Vessel to a Flow (Microwave) Reactor

et al. 2020

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We reported a novel simplified synthetic procedure for the preparation of monosubstituted piperazine derivatives which can now be easily prepared in a one-pot-one-step way from a protonated piperazine with no need of introduction of a protecting group. Reactions, proceeding either at room or higher temperatures in common solvents, involve heterogeneous catalysis by metal ions supported on commercial polymeric resins. A general synthetic scheme was successfully applied to afford a wide range of monosubstituted piperazines. Furthermore, we picked up a set of piperazine derivatives and studied the possibilities of microwave acceleration of given synthetic reactions to make them even more efficient. Our research proceeded from a simple batch technique to the construction of a flow microwave reactor prototype and resulted in promising findings which are summarized and discussed in the article.

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“…However, none of these reagent is suitable for industrial production due to drawbacks like high cost, toxic substance, complex work-up, etc. [9] In recent years, the demand for 1-amino anthraquinone (2) in the dye industry has increased rapidly. Hence, it is important to developed an efficient and scalable method for synthesis of 1-amino anthraquinone [1].…”

Section: Introductionmentioning

confidence: 99%

A Green and Scalable Synthesis of 1-Amino Anthraquinone

Lü

Yan

Qiu

et al. 2019

AJACR

Self Cite

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1-amino anthraquinone (2) is the most important intermediate in the synthesis of acid dyes. This paper presents a new method for the preparation of title compound (2) in a highly chemo- and regioselective reduction of 1-nitro anthraquinone (1) by NaHS in water under mild conditions. This protocol is clean, operationally simple, easy work-up and could be applied in the industrial production. Graphical_Abstract

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Efficient synthesis and antioxidant activities of N-heterocyclyl substituted Coenzyme Q analogues

Cited by 9 publications

References 34 publications

Eugenol derivatives: synthesis, characterization, and evaluation of antibacterial and antioxidant activities

Eugenol derivatives: synthesis, characterization, and evaluation of antibacterial and antioxidant activities

Simplified Procedure for General Synthesis of Monosubstituted Piperazines—From a Batch Reaction Vessel to a Flow (Microwave) Reactor

A Green and Scalable Synthesis of 1-Amino Anthraquinone

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