Design and synthesis of new 1,2,3-triazoles derived from eugenol and analogues with in vitro and in vivo activity against Trypanosoma cruzi

Reis, Rúbia Castro Fernandes Melo; Santos, Elda Gonçalves dos; Benedetti, Monique Dias; Reis, Adriana Cotta Cardoso; Brandão, Geraldo Célio; Silva, Glenda Nicioli da; Diniz, Lucas Abreu; Ferreira, Rafaela Salgado; Caldas, Ivo Santana; Braga, Saulo Fehelberg Pinto; Souza, Thiago Belarmino de

doi:10.1016/j.ejmech.2023.115622

Cited by 4 publications

(3 citation statements)

References 36 publications

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“…[159] Building on this progress, Reis et al (2023) synthesized 1,2,3-triazole analogs from eugenol, revealing that compound 16 outperformed BZN with an IC 50 of 7.3 μM for epimastigotes and 8.41 μM for trypomastigotes, using H9c2 cells. [160] Conceicao et al (2023) extended the exploration to pyridyl-thiazolidinones analogs, with compound 17 emerging as a standout candidate, demonstrating an IC 50 value of 0.64 μM for amastigotes and 0.9 μM for the trypomastigote form of T. cruzi. [161] All the compounds effectively surpassing the standard drug BZN.…”

Section: Synthesized Derivatives For the Treatment Of Chagas Diseasementioning

confidence: 99%

Alternative Approaches for the Treatment of Chagas Disease

Chaudhary,

Rajge,

Khandale

et al. 2024

ChemistrySelect

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Chagas disease (CD), or American trypanosomiasis, caused by the parasitic protozoa Trypanosoma cruzi, is a substantial global health burden. This comprehensive review explored the multifaceted landscape of CD treatment, providing a historical perspective on the development and discontinuation of benznidazole (BNZ) and nifurtimox (NF), the primary medications. Efforts towards a pediatric version of BZN in Brazil address demographic‐specific treatments, while concerns over drug resistance prompt the exploration of alternative medications like Amiodarone, Allopurinol, Posaconazole, Ravuconazole, and Fexinidazole, which were clinically tested as antichagasic drugs. In recent years, some of the synthesized derivative (1,3‐thiazoles, 4‐thiazolidinones, 2‐styrylquinolines, imidazole‐containing nitrophthalazine, and some others) were found to better activity as compared to standard drug. Traditional herbal alternatives (Resveratrol, curcumin, 1,8‐cineole, β‐pinene, and some others) rooted in traditional practices show promise, with various plant extracts exhibiting anti‐parasitic properties. The frontier of nanomedicine unfolds with studies on solid nanomedicines, PLA‐nanoparticles, ZIF‐8, BNZ carriers, and PLGA nanoparticles, showcasing improved drug delivery systems and controlled release mechanisms. The absence of a definitive vaccine accentuates ongoing research in recombinant antigens, peptide‐based vaccines, and nanoparticle formulations, with notable candidates like TcG1, TcG2, TcG4, MASPpep‐KLH, adenovirus vectors, Tc24 protein, and integrin activators. A novel strategy combining a recombinant protein vaccine with low dose BZN treatment presents promising results in a mouse model, emphasizing the urgency for further research and potential advancements in CD therapeutics.

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Section: Synthesized Derivatives For the Treatment Of Chagas Diseasementioning

confidence: 99%

Alternative Approaches for the Treatment of Chagas Disease

Chaudhary,

Rajge,

Khandale

et al. 2024

ChemistrySelect

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“…13 Since molecular modification of the structures of bioactive natural molecules is a widely used approach to obtain drug candidates with improved efficacy and reduced toxicity, eugenol has been used as a target molecule for the preparation of novel semi-synthetic bioactive compounds. [14][15][16][17][18] Recently, some of us have reported the synthesis and biological activity of a series of racemic mixtures of eugenol derivatives obtained by structural modifications of eugenol at the allyl group. 19 In particular, compound 1, whose structure is shown in Figure 1, showed in vitro antimicrobial activity.…”

Section: Introductionmentioning

confidence: 99%

Enantioselective high‐performance liquid chromatography combined with spectroscopic methods and theoretical calculations: A valid strategy to determine the absolute configuration of eugenol derivatives

Manetto,

Mazzoccanti,

Pulitelli

et al. 2024

Chirality

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The absolute configuration of three chiral eugenol derivatives was assigned by a multi‐step methodology based on enantioselective HPLC combined with spectroscopic and theoretical calculations. Milligram amounts of enantiopure forms used for stereochemical characterization were isolated by HPLC on the immobilized amylose‐based chiral stationary phase Chiralpak IG using normal phase elution conditions. The absolute configuration was indirectly determined for one of the three compounds by 1H NMR via methoxy‐α‐trifluoromethyl‐α‐phenylacetic acid derivatization (Mosher's acid). Comparison of the experimental and predicted electronic circular dichroism spectra confirmed the stereochemical assignment by Mosher's method and extended the absolute configuration assignment to two other chiral compounds.

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“…Although it is abundant in cloves ( Syzygium aromaticum ), it can also be found in various plants, giving them its typical pleasant odor and taste. The high value of this compound and its derivatives in the medicinal chemistry field is justified by its multifaceted activities, including its broad-spectrum antibacterial [ 7 , 8 ], antioxidant [ 9 , 10 ], antifungal [ 11 , 12 , 13 ], antiviral [ 14 , 15 , 16 ] and antiprotozoal [ 17 ] properties, among its many others [ 18 , 19 , 20 ].…”

Section: Introductionmentioning

confidence: 99%

Nature-Inspired Compounds: Synthesis and Antibacterial Susceptibility Testing of Eugenol Derivatives against H. pylori Strains

Carradori,

Ammazzalorso,

Niccolai

et al. 2023

Pharmaceuticals

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The antimicrobial properties of one of the most important secondary metabolites, Eugenol (EU), inspired us to design and synthesize three different series of derivatives enhancing its parent compound’s anti-Helicobacter pylori activity. Thus, we prepared semisynthetic derivatives through (A) diazo aryl functionalization, (B) derivatization of the hydroxy group of EU, and (C) elongation of the allyl radical by incorporating a chalcogen atom. The antibacterial evaluation was performed on the reference NCTC 11637 strain and on three drug-resistant clinical isolates and the minimal inhibitory and bactericidal concentrations (MICs and MBCs) highlight the role of chalcogens in enhancing the antimicrobial activity (less than 4 µg/mL for some compounds) of the EU scaffold (32–64 µg/mL).

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Design and synthesis of new 1,2,3-triazoles derived from eugenol and analogues with in vitro and in vivo activity against Trypanosoma cruzi

Cited by 4 publications

References 36 publications

Alternative Approaches for the Treatment of Chagas Disease

Alternative Approaches for the Treatment of Chagas Disease

Enantioselective high‐performance liquid chromatography combined with spectroscopic methods and theoretical calculations: A valid strategy to determine the absolute configuration of eugenol derivatives

Nature-Inspired Compounds: Synthesis and Antibacterial Susceptibility Testing of Eugenol Derivatives against H. pylori Strains

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