Lawsone in organic synthesis

Jordão, Alessandro K.; Vargas, Maria D.; Pinto, Ângelo C.; Silva, Fernando de Carvalho da; Ferreira, Vı́tor F.

doi:10.1039/c5ra12785h

Cited by 81 publications

(45 citation statements)

References 286 publications

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“…The presence of waves III c and IV c is also unexpected. The II a band, which is related to the oxidation of the dianion (CQ 2− ), is broad and related to the expected isomerization of ortho / para ‐quinone caused by opening and recyclization of the dihydropyran ring (C) . Waves III c and IV c are related to the reduction of products generated herein and will not be considered further.…”

Section: Resultsmentioning

confidence: 75%

Reactive Oxygen Species Release, Alkylating Ability, and DNA Interactions of a Pterocarpanquinone: A Test Case for Electrochemistry

et al. 2016

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The electrochemistry of a redox‐based bioactive pterocarpanquinone, designated as LQB‐118, and its precursor chromenquinone (CQ) was investigated in protic and aprotic media with a focus on the reduction mechanism in both media, the reactivity with oxygen, and the interaction with biological targets, such as DNA. UV/Vis spectroelectrochemistry clarified the proposed mechanism. The appearance of bands at λ=331, 400, and 600 nm suggests the generation of transient quinonemethides (QM). Electrochemical experiments revealed homogeneous electron transfer to oxygen. LQB‐118 itself interacts with calf‐thymus DNA and ssDNA in solution. It, and its electrogenerated intermediates, have been shown to decrease the diagnostic oxidation peaks of guanosine and adenosine residues. These results, together with electrochemical evidence for the formation of QMs and the reductive addition of thiols, partly explain the reported cytotoxic and parasiticidal effects of this quinone. Overall, the electrochemical methods do well to predict the molecular mechanism of the biological activity of the present class of compounds. As an additional competitive advantage, electrochemistry allows reductive cleavage in situ, the characterization of the generated intermediate, the calculation of the number of transferred electrons, and positively mimics in vitro and in vivo experiments.

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Section: Resultsmentioning

confidence: 75%

Reactive Oxygen Species Release, Alkylating Ability, and DNA Interactions of a Pterocarpanquinone: A Test Case for Electrochemistry

et al. 2016

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“…Henna extracts are now commercialized for skin, wool and cotton dyeing purposes in Asia and Africa. Despite this broad spectrum of biological properties, the phytotoxicity of lawsone has not been fully studied . It is also well known that the position of the hydroxyl group in this family of compounds is crucial for their biological activities as it affects the redox potentials and pro‐oxidant activities …”

Section: Introductionmentioning

confidence: 99%

Structure‐activity relationship studies on naphthoquinone analogs. The search for new herbicides based on natural products

Durán

Chinchilla

Molinillo

et al. 2019

Pest Management Science

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BACKGROUND Allelopathy and bioassays constitute fundamental tools in the search for new herbicide templates. The work described here is a continuation of a previous study focused on the structure–activity relationships between transport phenomena and phytotoxic activity. Different modifications were made to the naphthoquinone backbone and two key factors were identified as being responsible for changes in activity: lipophilicity and the nature of the functional group. The study of other naturally occurring and semi‐synthetic naphthoquinones was also proposed. RESULTS A total of 12 5‐O‐acyl plumbagins and 18 analogs with unsaturated and aromatic substituents at positions 2 and 5 were synthesized. These compounds were evaluated in the wheat coleoptile bioassay and against Standard Target Species (STS) and three weeds, namely Echinochloa crus‐galli L., Lolium rigidum Gaud. and Lolium perenne L. A strong structure–function relationship was observed for the different naphthoquinones and root and shoot length were the parameters that were most affected. CONCLUSION Strong inhibitory effects were observed for the isomeric forms 23 and 33 and the derivatives with a free hydroxyl group, i.e. 24 and 30, gave values higher than 70% inhibition for root length in barnyardgrass and perennial ryegrass. These results highlight the potential of these compounds as models in the development of herbicides based on natural products. © 2019 Society of Chemical Industry

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“…Quinones are widely distributed in nature, and their derivatives are very important as synthetic and natural products in many diverse areas of chemistry and biochemistry. Because of a deep relationship between quinones and the biochemical processes of cells, these substances have been greatly explored in the synthesis of several bioactive compounds with valuable biological activities . For instance, 2‐hydroxy‐1,4‐naphthoquinone (lawsone) is one of the most useful and the simplest naturally occurring naphthoquinones.…”

Section: Introductionmentioning

confidence: 99%

An Efficient Synthesis of Benzo[g]thiazolo[2,3‐b]quinazolin‐4‐ium and Benzo[g]benzo[4,5]thiazolo[2,3‐b]quinazolin‐14‐ium Hydroxides by a One‐pot, Three‐component Reaction under Green Conditions

Nouri

Marjani

Khalafy

2019

Journal of Heterocyclic Chem

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A new series of benzo[g]thiazolo[2,3‐b]quinazolin‐4‐ium and benzo[g]benzo[4,5]thiazolo[2,3‐b]quinazolin‐14‐ium hydroxide derivatives have been synthesized by the one‐pot, three‐component reaction of aryl glyoxal monohydrates, 2‐hydroxy‐1,4‐naphthoquinone, and 2‐aminothiazole or 2‐aminobenzothiazole in the presence of triethylamine and p‐toluenesulfonic acid as organocatalysts in H2O/acetone (2:1) at room temperature. This method offers mild reaction conditions, excellent yields, easy workup, and readily accessible starting materials and catalysts.

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Lawsone in organic synthesis

Abstract: Lawsone has been used as the starting material for the synthesis of a variety of biologically active compounds and materials.

Cited by 81 publications

References 286 publications

Reactive Oxygen Species Release, Alkylating Ability, and DNA Interactions of a Pterocarpanquinone: A Test Case for Electrochemistry

Reactive Oxygen Species Release, Alkylating Ability, and DNA Interactions of a Pterocarpanquinone: A Test Case for Electrochemistry

Structure‐activity relationship studies on naphthoquinone analogs. The search for new herbicides based on natural products

An Efficient Synthesis of Benzo[g]thiazolo[2,3‐b]quinazolin‐4‐ium and Benzo[g]benzo[4,5]thiazolo[2,3‐b]quinazolin‐14‐ium Hydroxides by a One‐pot, Three‐component Reaction under Green Conditions

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