On the search for potential anti-Trypanosoma cruzi drugs: Synthesis and biological evaluation of 2-hydroxy-3-methylamino and 1,2,3-triazolic naphthoquinoidal compounds obtained by click chemistry reactions

Júnior, Eufrânio N. da Silva; Melo, Isadora M.M. de; Diogo, Emilay B. T.; Costa, Verenice A.; Filho, José Dias de Souza; Valença, Wagner O.; Câmara, Celso A.; Oliveira, Ronaldo N. de; Araújo, Alexandre Suman de; Emery, Flávio da Silva; Santos, Marcelo R. dos; Simone, C. A. De; Menna-Barreto, Rubem F.S.; Castro, Solange L. de

doi:10.1016/j.ejmech.2012.03.039

Cited by 62 publications

(12 citation statements)

References 42 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…IVS320 was even more active than the analogs originated from the insertion of 1,2,3-triazole in the 1,4-naphthoquinone structure, where they showed IC 50 that ranged from 10 to 17 µM [ 31 ]. In addition, IVS320 was the most effective among the 2-aminonaftoquinone derivatives in which, despite the increased time of exposure to the parasite, showed IC 50 values around 7.5 µM [ 32 ].…”

Section: Trypanocidal Activitymentioning

confidence: 99%

Characterization and Trypanocidal Activity of a Novel Pyranaphthoquinone

et al. 2017

View full text Add to dashboard Cite

Chagas disease is an endemic parasitic infection that occurs in 21 Latin American countries. New therapies for this disease are urgently needed, as the only two drugs available (nifurtimox and benznidazol) have high toxicity and variable efficacy in the disease’s chronic phase. Recently, a new chemical entity (NCE) named Pyranaphthoquinone (IVS320) was synthesized from lawsone. We report herein, a detailed study of the physicochemical properties and in vitro trypanocidal activity of IVS320. A series of assays were performed for characterization, where thermal, diffractometric, and morphological analysis were performed. In addition, the solubility, permeability, and hygroscopicity of IVS320 were determined. The results show that its poor solubility and low permeability may be due to its high degree of crystallinity (99.19%), which might require the use of proper techniques to increase the IVS320’s aqueous solubility and permeability. The trypanocidal activity study demonstrated that IVS320 is more potent than the reference drug benznidazole, with IC50/24 h of 1.49 ± 0.1 μM, which indicates that IVS320 has potential as a new drug candidate for the treatment of Chagas disease.

show abstract

Section: Trypanocidal Activitymentioning

confidence: 99%

Characterization and Trypanocidal Activity of a Novel Pyranaphthoquinone

et al. 2017

View full text Add to dashboard Cite

show abstract

“…1,2,3-Triazole represents a class of compounds that has awakened an interest in our research group by the synthesis of new heterocyclic derivatives and their biological evaluation [12–14]. In this work the synthesis and anti-inflammatory activity of six compounds based on 1,2,3-triazoles it were performed.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Anti-Inflammatory Activity of New Alkyl-Substituted Phthalimide 1H-1,2,3-Triazole Derivatives

Assis

Silva

Oliveira

et al. 2012

The Scientific World Journal

View full text Add to dashboard Cite

Four new 1,2,3-triazole phthalimide derivatives with a potent anti-inflammatory activity have been synthesized in the good yields by the 1,3-dipolar cycloaddition reaction from N-(azido-alkyl)phthalimides and terminal alkynes. The anti-inflammatory activity was determined by injecting carrageenan through the plantar tissue of the right hind paw of Swiss white mice to produce inflammation. All the compounds 3a–c and 5a–c exhibited an important anti-inflammatory activity; the best activity was found for the compounds 3b and 5c, which showed to be able to decrease by 69% and 56.2% carrageenan-induced edema in mice. These compounds may also offer a future promise as a new anti-inflammatory agent.

show abstract

“…Among the known biological activities of compounds with a quinone structure, these substances stand out for their antiprotozoal activity. For example, three synthesized naphthofuranquinone C-allyl lawsone derivatives were active against Trypanosoma cruzi trypomastigotes [8]. When used as therapeutic agents, quinonoidal ligand cytotoxic activity operates through various mechanisms, such as redox cycling, intercalation, inducing DNA strand breaks, arylation, alkylation via quinone methide formation and free radical generation [20].…”

Section: Resultsmentioning

confidence: 99%

“…Quinones are a well-known class of compounds with a broad natural distribution; they exhibit a diverse spectra of biological activities, including antitumor [1,2], molluscicidal [3], leishmanicidal [4,5], bactericidal, fungicidal [6,7] and trypanocidal functions [8], and they act as inhibitors of the reverse transcriptase enzyme of HIV-1 [9] and human topoisomerase II [10]. The conjugated 1,4-dicarbonyl or 1,2-dicarbonyl moiety in the most well-known para - and ortho -quinone molecular structures confers specific properties and a reactivity that facilitates participation in redox processes, which are likely related to these substances’ mechanisms of action [11,12].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Leishmanicidal Activity and Theoretical Evaluations of a Series of Substituted bis-2-Hydroxy-1,4-Naphthoquinones

et al. 2014

View full text Add to dashboard Cite

A series of eight substituted bis-2-hydroxy-1,4-naphthoquinone derivatives was synthesized through lawsone condensation with various aromatic and aliphatic aldehydes under mild acidic conditions. The title compounds were evaluated for antileishmanial activity in vitro against Leishmania amazonensis and Leishmania braziliensis promastigotes; six compounds showed good activity without significant toxic effects. The compound with the highest activity was used for an in vivo assay with Leishmania amazonensis.

show abstract

On the search for potential anti-Trypanosoma cruzi drugs: Synthesis and biological evaluation of 2-hydroxy-3-methylamino and 1,2,3-triazolic naphthoquinoidal compounds obtained by click chemistry reactions

Cited by 62 publications

References 42 publications

Characterization and Trypanocidal Activity of a Novel Pyranaphthoquinone

Characterization and Trypanocidal Activity of a Novel Pyranaphthoquinone

Synthesis and Anti-Inflammatory Activity of New Alkyl-Substituted Phthalimide 1H-1,2,3-Triazole Derivatives

Synthesis, Leishmanicidal Activity and Theoretical Evaluations of a Series of Substituted bis-2-Hydroxy-1,4-Naphthoquinones

Contact Info

Product

Resources

About