Synthesis, Antituberculosis Activity and Molecular Docking Studies for Novel Naphthoquinone Derivatives

Paengsri, W; Lee, Vannajan Sanghiran; Chong, Wei Lim; Wahab, Habibah A.; Baramee, Apiwat

doi:10.3923/ijbc.2012.69.88

Cited by 12 publications

(9 citation statements)

References 8 publications

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“…It was found that compound 10a showed the high activity anti-tuberculosis among other compounds, although cytotoxicity issues have been observed when evaluated on Verocells for further concerns. 39 The synthesis of two new PPI-G1 dendrimers containing lowsone 11 as pharmacophoer is reported by Ndiaye and coworkers. The compounds were synthesized in course of Mannich reaction involving lawsone (2), the commercial PPI-G1(polypropyleneimine-G1) dendrimer with functional amino groups on the exterior and acetaldehyde or benzaldehyde in 4 : 1 : 4 molar ratio in absolute EtOH at room temperature for overnight in the dark (Scheme 7).…”

Section: Uncatalyzed Reactionsmentioning

confidence: 99%

Mannich bases derived from lawsone and their metal complexes: synthetic strategies and biological properties

2020

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Section: Uncatalyzed Reactionsmentioning

confidence: 99%

Mannich bases derived from lawsone and their metal complexes: synthetic strategies and biological properties

2020

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“…[11][12][13][14] Within these studies, the 1,4-naphthoquinone analogues have been found to possess not only antimalarial activity but also a diverse range of biological activities, such as antioxidant, antibacterial, antitumor, antituberculosis activities. [14][15][16][17][18] Aminonaphthoquinone belongs to the quinone family which possesses an interesting scaffold conveying potential for a range of pharmacological applications. 19,20) Previously published literature reported that incorporation of amino groups or N-containing fragments into the 1,4-naphthoquinone skeleton resulted in increased levels of antiplasmodial activity, [20][21][22] as well as many other significantly beneficial biological properties such as antitumor, antifungal, antibacterial, antiplatelet, anti-allergic and anti-inflammatory activities.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Evaluation of 2-Hydroxy-1,4-naphthoquinone Derivatives as Potent Antimalarial Agents

Paengsri

Promsawan

Baramee

2021

CHEMICAL & PHARMACEUTICAL BULLETIN

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A series of 3-substituted-2-hydroxy-1,4-naphthoquinone derivatives with a variety of side chains were successfully synthesized by Mannich reaction of 2-hydroxy-1,4-naphthoquinone (lawsone) with selected amines and aldehydes. All substances (1-16) were evaluated for in-vitro antimalarial activity against strains of Plasmodium falciparum by microculture radioisotope technique. Bioassay data revealed that ten derivatives (1-8,11 and 13) displayed significantly good activity with values of IC 50 ranging from 0.77 to 4.05 g/mL. The best biological profile (IC 50 = 0.77 g/mL) was observed in compound 1, possessing a n-butyl substituted aminomethyl group. Experimental results support the potential use of our active Mannich components as promising antimalarial agents in the fight against malaria infections and multidrug resistance problems.

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“…The chemical modification of lawsone has led to compounds with activity against tumor cells and fungi . Lawsone Mannich bases have shown particularly promising activities against cancer cells and parasites including Trypanosoma brucei brucei and Entamoeba histolytica . We have previously found that longer alkyl chains attached to the naphthoquinone scaffold as in compound 1b led to enhanced bioactivities (Figure ) .…”

Section: Introductionmentioning

confidence: 99%

Antiparasitic activities of new lawsone Mannich bases

Nasr

Jentzsch

Winter

et al. 2019

Archiv der Pharmazie

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A series of new lawsone Mannich bases derived from salicylaldehydes or nitrofurfural were prepared and tested for their activities against Leishmania major, Toxoplasma gondii, and Trypanosoma brucei brucei parasites. The hydrochloride salts 5a and 6a of the Mannich bases 2a and 3a, derived from unsubstituted salicylaldehyde and longchained alkyl amines, were selectively and strongly active against T. gondii cells and appear to be new promising drug candidates against this parasite. Compound 6ashowed an even higher activity against T. gondii than the known lawsone Mannich base 1b. Compound 4a, derived from salicylaldehyde and 2-methylaminopyridine, was also distinctly active against T. gondii cells. The derivatives 3a (salicyl derivative), 3b(3,5-dichloro-2-hydroxyphenyl derivative), and 3d (5-nitrofuranyl derivative) as well as the hydrochlorides 6a and 6b were also efficacious against T. b. brucei cells with compounds 3a and 3b being more selective for T. b. brucei over Vero cells when compared with the known control compound 1b. The derivatives 5a, 5c, 6a, and 6c proved to be up to five times more active than 1b against L. major promastigotes and up to four times more efficacious against L. major amastigotes. K E Y W O R D Santiparasitic drugs, lawsone, Mannich base, neglected tropical diseases, salicyl derivatives

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Synthesis, Antituberculosis Activity and Molecular Docking Studies for Novel Naphthoquinone Derivatives

Cited by 12 publications

References 8 publications

Mannich bases derived from lawsone and their metal complexes: synthetic strategies and biological properties

Mannich bases derived from lawsone and their metal complexes: synthetic strategies and biological properties

Synthesis and Evaluation of 2-Hydroxy-1,4-naphthoquinone Derivatives as Potent Antimalarial Agents

Antiparasitic activities of new lawsone Mannich bases

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