Review on Natural Coumarin Lead Compounds for Their Pharmacological Activity

Venugopala, Katharigatta N.; Rashmi, V.; Odhav, Bharti

doi:10.1155/2013/963248

Cited by 717 publications

(529 citation statements)

References 78 publications

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“…1928 third process was the hetero Diels-Alder of o-QMs with several styrenes, forming α-and β-pyranaphthoquinones 11a and 11b. 28 Xanthenes fused with ortho-quinone or para-quinone (12)(13)(14)(15)(16) have been reported in the literature (Figure 2). [29][30][31][32][33][34][35][36][37] More recently, our research group became interested in the synthesis of 6H-dibenzo[b,h]xanthenes (16) that contain the two asymmetrical naphthoquinone moieties, which were prepared selectively under solvent-free conditions.…”

Section: Introductionmentioning

confidence: 99%

“…13 This family of compounds presents a wide variety of biological activities, including anti-inflammatory, antibacterial, antifungal, antiviral and anticancer. 14,15 In Figure 1, we highlight the following important natural and synthetic naphthoquinones that match this profile: lawsone (1), β-lapachone (2), α-lapachone (3), urdamycinone B (4), estreptonigrin (5), 4-hydroxycoumarin (6), calanolide A (7) and osthole (8). [16][17][18][19] Because of the importance of these naphthoquinones and coumarins, the search for new, simple and efficient methods of preparation of structurally related compounds remains of great interest.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of New Xanthenes Based on Lawsone and Coumarin via a Tandem Three‑Component Reaction

Cardoso¹,

Forezi²,

Cavalcante³

et al. 2017

J. Braz. Chem. Soc.

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The synthesis of several new xanthenes based on the 1,3-dicarbonyl scaffolds lawsone and coumarin was developed using tandem three-component reactions involving the reagents ortho-hydroxybenzaldehyde, as bifunctional reagent, and an appropriate thiol. These reactions generated two series of para-and ortho-naphthoxanthenes that are structurally related to α-and β-pyranaphthoquinones and one series of coumarin-xanthene derivatives.Keywords: 2-hydroxy-1,4-naphthoquinone, coumarin, multi-component reactions, organocatalysis, ortho-quinone methide IntroductionXanthenes are a class of heterocyclic compounds that are extensively found in natural products and have many biological applications and several applications in materials science. [1][2][3] Xanthenes are prepared by several synthetic methods and structurally possess carbocyclic or heterocyclic substituents fused to a central pyran ring. In general, the most commonly used methods for their preparation involve a cycloaddition reaction of a 1,3-dicarbonyl compound with aldehydes to form an adduct, a reactive α,β-unsaturated intermediate, which reacts with an appropriate nucleophile in the second step. [4][5][6] Lawsone (1) and 4-hydroxycoumarin (6) are two 1,3-dicarbonyl compounds that have been extensively used by synthetic organic chemists because of their peculiar chemical structures and their relationships with biologically important natural products. 7 Indeed, these natural products have a large variety of biological activity that has been studied in recent decades and stimulated the synthesis of a large number of synthetic analogues. [8][9][10][11] Naphthoquinones play vital roles in several biological processes and are considered to be of great importance in medicinal chemistry. Naphthoquinones are often associated with various biological activities, including anticancer, antibacterial, antimalarial, trypanocidal, tuberculostatic and fungicidal activities. 12 Some natural coumarins are found as secondary metabolites from plants, bacteria and fungi. 13 This family of compounds presents a wide variety of biological activities, including anti-inflammatory, antibacterial, antifungal, antiviral and anticancer. 14,15 In Figure 1, we highlight the following important natural and synthetic naphthoquinones that match this profile: lawsone (1), β-lapachone (2), α-lapachone (3), urdamycinone B (4), estreptonigrin (5), 4-hydroxycoumarin (6), calanolide A (7) and osthole (8). [16][17][18][19] Because of the importance of these naphthoquinones and coumarins, the search for new, simple and efficient methods of preparation of structurally related compounds remains of great interest.Tandem multi-component reactions (MCR) are convergent syntheses that begin with three or more reactants and, preferably, end with only one formed product that contains all of the starting atoms. 20 Usually, these types of reactions have a high atom economy and a high possibility of diversifying the structures of the final products. MCRs are important in industrial applications 21 and the devel...

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis of New Xanthenes Based on Lawsone and Coumarin via a Tandem Three‑Component Reaction

Cardoso¹,

Forezi²,

Cavalcante³

et al. 2017

J. Braz. Chem. Soc.

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“…A cumarina apresenta ações biológicas tradicionalmente conhecidas para o tratamento de doenças respiratórias, devido às ações broncodilatadora, expectorante, antiinflamatória e antialérgica, tornando o guaco um potente fitoterápico contra asma e bronquite 1 . Há mais de 1300 tipos de cumarinas identificadas, distribuídas em mais de 30 famílias, totalizando sua presença em cerca de 150 espécies na natureza 10 . Estruturalmente as cumarinas são lactonas do ácido o-hidróxi-cinâmico, sendo o representante mais simples a cumarina (1,2-benzopirona).…”

Section: Introductionunclassified

Solubilização Da Cumarina Em Meio Aquoso E Determinação Da Sua Atividade Antibacteriana

et al. 2016

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A pesquisa teve como objetivo estabelecer o menor grau etanólico para a solubilização da cumarina em meio aquoso e avaliar a sua atividade antibacteriana. Avaliou-se a solubilidade em água destilada e soluções etanólicas 10%, 30%, 50% e 70%, sendo estabelecida a solução etanólica a 30%, como solvente. As concentrações 1. 024, 512, 256, 128, 64, 32, 16, 8, 4 e 2µg/mL (p/v) Maria, v. 42, n.2, p. 195-201, jul./dez. 2016 SOLUBILIZAÇÃO DA CUMARINA EM MEIO AQUOSO E DETERMINAÇÃO DA SUA ATIVIDADE ANTIBACTERIANA COUMARIN SOLUBILIZATION IN AQUEOUS MEDIUM AND DETERMINATION OF THE ITS ACTIVITY ANTIBACTERIAL ABSTRACTThe research aimed to establish the lowest degree ethanolic to solubilize the coumarin in aqueous and to evaluate its antibacterial activity. It was evaluated the solubility in distilled water and solutions ethanolic 10%, 30%, 50% and 70%, it is set at 30% ethanolic solution as a solvent.. The concentrations of 1.024, 512, 256, 128, 64, 32, 16, 8, 4, and 2µg/mL (w/v) of coumarin were tested by the microdilution method against bacteria Staphylococcus aureus (ATCC 14458), Staphylococcus epidermidis (ATCC 12228), Bacillus cereus (ATCC 11778), Listeria monocytogenes (ATCC 7644), Escherichia coli (ATCC 11229), Salmonella enterica subsp. enterica sorovar. Typhimurium (ATCC 13311), Salmonella enterica subsp. enterica sorovar. Typhi (ATCC 19214) e Shigella flexneri (ATCC 12022). The ethanolic solution at 30% of coumarin has significant inhibitory effect on Gram positive bacteria, showing MIC <2µg/mL for S. epidermidis, B. cereus and L. monocytogenes.

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“…treatment of chronic diseases [12]. In this sense, the modulation of the coumarin ring, specifically when introducing a heteroaromatic ring (i.e.…”

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<strong>QSAR Model: Prediction of the Clastogenic Potential of 3-Arylcoumarins</strong>

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León

et al. 2017

Proceedings of 3rd International Electronic Conference on Medicinal Chemistry

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Abstract. Drug discovery is a challenging task for researchers due to the complexity of biomolecules involved in pathologic processes. Design and development of efficient drugs is still urgent for several diseases.Cheminformatics tools are useful to better understand the interaction between new chemical entities and their targets. We studied a selected series of 3-arylcoumarins with antioxidant potential, and how their chemical features can contribute for the clastogenic activity. A virtual screening, based on the TOPSMODE approach, using a clastogenic model, was performed. The results suggest that the presence and position of hydroxyl groups in the scaffold is important for the activity. This communication is focused on cheminformatics, and its applications in drug effectiveness and safety.

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Review on Natural Coumarin Lead Compounds for Their Pharmacological Activity

Cited by 717 publications

References 78 publications

Synthesis of New Xanthenes Based on Lawsone and Coumarin via a Tandem Three‑Component Reaction

Synthesis of New Xanthenes Based on Lawsone and Coumarin via a Tandem Three‑Component Reaction

Solubilização Da Cumarina Em Meio Aquoso E Determinação Da Sua Atividade Antibacteriana

<strong>QSAR Model: Prediction of the Clastogenic Potential of 3-Arylcoumarins</strong>

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