The chemistry and biology of lapachol and related natural products α and β-lapachones

Ravelo, Ángel G.; Estévez‐Braun, Ana; Pérez-Sacau, Elisa

doi:10.1016/s1572-5995(03)80017-0

Cited by 23 publications

(19 citation statements)

References 134 publications

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“…Lapachol (1) was isolated by extraction of the powdered wood of Tabebuia impetiginosa (Bignoniaceae) with a cold soln. of Na 2 CO 3 1% [6]. b-Lapachone (2) was obtained by intramolecular cyclization of 1 with conc.…”

Section: Experimental Partmentioning

confidence: 99%

“…The toxicity and therapeutic activities of these compounds involve the formation of reactive oxygen species [5]. Among naturally occurring naphthoquinones, lapachol ( 2-hydroxy-3-(3-methylbut-2-enyl)naphthalene-1,4-dione; 1) and b-lapachone ( 3,4-dihydro-2,2-dimethyl-2H-naphtho [1,2-b]pyran-5,6-dione; 2), isolated from the heartwood of trees belonging to the Bignoniaceae family, stand out for the variety of biological activities, e.g., antitumor, bactericidal, fungicidal, virucidal, and trypanocidal [6].…”

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confidence: 99%

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Antiplasmodial Activity of Naphthoquinones Related to Lapachol andβ-Lapachone

Pérez-Sacau

Estévez‐Braun

Ravelo

et al. 2005

Chemistry & Biodiversity

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The in vitro antiplasmodial activity of 26 naphthoquinone derivatives related to the natural lapachol (1) and beta-lapachone (2) was tested. Ten of these derivatives are reported for the first time. The evaluation was performed on cultures of F32 strain of Plasmodium falciparum, and some derivatives displayed attractive in vitro activities (IC50 < 10 microM). Based on these results, some structure-activity relationships have been determined.

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Section: Experimental Partmentioning

confidence: 99%

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confidence: 99%

Antiplasmodial Activity of Naphthoquinones Related to Lapachol andβ-Lapachone

Pérez-Sacau

Estévez‐Braun

Ravelo

et al. 2005

Chemistry & Biodiversity

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“…1,4-Naphthoquinones are a class of compounds broadly studied in natural products chemistry and medicinal chemistry [4,5,6]. Within these studies, the antimalarial activity has been reported for several 1,4-naphthoquinones [7,8,9,10,11,12,13,14].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antiplasmodial Activity of 1,2,3-Triazole-Naphthoquinone Conjugates

et al. 2019

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A series of 34 1,2,3-triazole-naphthoquinone conjugates were synthesized via copper-catalyzed cycloaddition (CuAAC). They were evaluated for their in vitro antimalarial activity against chloroquine-sensitive strains of Plasmodium falciparum and against three different tumor cell lines (SKBr-3, MCF-7, HEL). The most active antimalarial compounds showed a low antiproliferative activity. Simplified analogues were also obtained and some structure–activity relationships were outlined. The best activity was obtained by compounds 3s and 3j, having IC50 of 0.8 and 1.2 μM, respectively. Molecular dockings were also carried on Plasmodium falciparum enzyme dihydroorotate dehydrogenase (PfDHODH) in order to rationalize the results.

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“…Naturally occurring naphthoquinones comprise an important class of natural products with a wide range of biological activity 1,2 arising from their ability to cause DNA modification via redox cycling of the quinone moiety and the generation of reactive oxygen species. 2c,3 In the structurally diverse naphthoquinone natural products, dihydropyranonaphthoquinones (a-and b-lapachones) have attracted special attention because of their promising antitumor ability, 4 among various other bioactivities. Heterocyclic naphthoquinones of the lapachone family are found as minor components in the stem bark of many trees of the Tabebuia genus in Central and South America.…”

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confidence: 99%

Synthesis of Siloxy-α-Lapachone Derivatives by Chemo- and Regioselective Diels-Alder Reactions of 3-Methylene-1,2,4-naphthotriones with Silyl Enol Ethers

Peng¹,

Liu²,

Lu³

et al. 2008

Synthesis

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o-Quinone methides, generated in situ from the Knoevenagel condensation of 2-hydroxy-1,4-naphthoquinone with aliphatic and aromatic aldehydes, take part in chemoselective hetero-Diels-Alder reactions with silyl enol ethers to give a series of siloxy-containing naphtho[2,3-b]pyran-5,10-dione (a-lapachone) derivatives in moderate to high yield. These reactions regioselectively gave a-lapachone derivatives with an acetal structure. This regioselectivity can be rationalized by considering the frontier molecular orbital interactions of the o-quinone methide with the silyl enol ether, and by taking into account the energetically more favorable pathway leading to a zwitterion-like transition state of lower energy in a Michael addition between the two reactants.Naturally occurring naphthoquinones comprise an important class of natural products with a wide range of biological activity 1,2 arising from their ability to cause DNA modification via redox cycling of the quinone moiety and the generation of reactive oxygen species. 2c,3 In the structurally diverse naphthoquinone natural products, dihydropyranonaphthoquinones (a-and b-lapachones) have attracted special attention because of their promising antitumor ability, 4 among various other bioactivities. Heterocyclic naphthoquinones of the lapachone family are found as minor components in the stem bark of many trees of the Tabebuia genus in Central and South America. 5 a-Lapachones have a wider distribution than b-lapachones, and are additionally found in Ekmanianthe longiflora in America 6 and in Capalta ovata trees in many east Asian countries. 7 Of these pyranonaphthoquinones, b-lapachone derivatives have so far received the most extensive investigations, mainly owing to their stronger antitumor activity. 8 However, more recent investigations have shown that a-lapachone is an effective DNA topoisomerase II inhibitor and is a potential lead compound for the development of drugs for the treatment of multidrug resistant cell lines with low expressions of topoisomerase II. 9 In addition, alapachone derivatives possess their own special biological activities ranging across antibacterial, 10 antipsoriatic, 11 antifungal 12 and trypanosidal 13 activity. Furthermore, in the recently rapidly developing research area of cancer chemoprevention as a promising tool in cancer control, 14 quinone compounds have proven to be one of the most important classes of potential cancer chemopreventing agents (antitumor promoters). 15 Extensive studies of a large variety of quinone compounds points to the 1,4-and 1,2-naphthoquinones, including a-and b-lapachones, as privileged structures, 16 with the 1,4-naphthoquinones having great cancer-preventing potential. 17 Structureactivity relationship studies in lapachones have shown that structural modification to the redox center (the quinone functionality) 13a and the C-ring, 13a,16b leads to significant changes in bioactivities and are important in the search for possible lead compounds with more potent pharmaceutical activity and less toxicity. L...

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The chemistry and biology of lapachol and related natural products α and β-lapachones

Cited by 23 publications

References 134 publications

Antiplasmodial Activity of Naphthoquinones Related to Lapachol andβ-Lapachone

Antiplasmodial Activity of Naphthoquinones Related to Lapachol andβ-Lapachone

Synthesis and Antiplasmodial Activity of 1,2,3-Triazole-Naphthoquinone Conjugates

Synthesis of Siloxy-α-Lapachone Derivatives by Chemo- and Regioselective Diels-Alder Reactions of 3-Methylene-1,2,4-naphthotriones with Silyl Enol Ethers

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