Google Académico | Citações: 16429 | índice h: 32 | índice i10: 482
Síntesis y actividad antimicrobiana de la chalcona tiofénica y el derivado de pirazol
PDF (inglés)

Palabras clave

Chalcona
Derivado de pirazol
Actividad antimicrobiana
CMI

Cómo citar

Síntesis y actividad antimicrobiana de la chalcona tiofénica y el derivado de pirazol. (2025). Revista Eletrônica Acervo Saúde, 25(10), e21827. https://doi.org/10.25248/reas.e21827.2025

Copyright © | Todos los derechos reservados.

La revista posee los derechos de autor exclusivos para la publicación de este artículo en los términos de la ley brasileña 9610/98.

Reproducción parcial
El uso de partes de los textos, figuras y cuestionario del artículo es libre, siendo obligatoria la citación de los autores y revista.

Reproducción total
Está expresamente prohibido y debe ser autorizado por la revista.

Resumen

Objetivo: Analizar la actividad antimicrobiana de una chalcona tiofénica y un derivado de pirazol sintetizados a través de rutas químicas específicas. Métodos: Este es un estudio experimental in vitro. La chalcona tiofénica (GA-01) se sintetizó por condensación aldólica y su derivado de pirazol (GA-04) por ciclocondensación con tiosemicarbazida. Los compuestos se caracterizaron por RMN de ¹H y ¹³C. La actividad antimicrobiana se evaluó determinando la concentración mínima inhibitoria (CMI) contra Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus y Candida albicans, utilizando el método de microdilución en placa. Para investigar el mecanismo de acción, se realizó un ensayo con sorbitol 0,8 M, evaluando el impacto osmoprotector en la eficacia de los compuestos. Resultados: La chalcona GA-01 tuvo una CMI de 128 μg/mL para todas las cepas. El GA-04 mostró mayor actividad, con una CMI de 64 μg/mL para bacterias y 4 μg/mL para C. albicans. En el ensayo con sorbitol, se observó un aumento de la CMI para ambos compuestos, lo que sugiere una acción sobre la pared celular microbiana. Conclusión: Los compuestos sintetizados mostraron un potencial antimicrobiano prometedor, con énfasis en el nuevo derivado de pirazol (GA-04), que demostró una mayor eficacia. Los resultados indican que estos compuestos son prototipos para el desarrollo de nuevos agentes antimicrobianos.

PDF (inglés)

Referencias

ANSARI A, et al. Review: biologically active pyrazole derivatives. New journal of chemistry, 2017; 41(1): 16–41.

ARDIANSAH, B. Chalcones bearing N, O, and S-heterocycles: Recent notes on their biological significances. Journal of applied pharmaceutical science, 2019; 9(8): 117–129.

BERTOLDO JB, et al. Synthetic compounds from an in house library as inhibitors of falcipain-2 from Plasmodium falciparum. Journal of enzyme inhibition and medicinal chemistry, 2015; 30(2): 299–307.

BHAT MA, et al. Synthesis, anti-inflammatory and neuroprotective activity of pyrazole and pyrazolo[3,4-d]pyridazine bearing 3,4,5-trimethoxyphenyl. Medicinal chemistry research: an international journal for rapid communications on design and mechanisms of action of biologically active agents, 2017; 26(7): 1557–1566.

BORCHHARDT DM, et al. Biochemical evaluation of a series of synthetic chalcone and hydrazide derivatives as novel inhibitors of cruzain from Trypanosoma cruzi. Journal of the Brazilian Chemical Society, 2010; 21(1):142–150.

BOULEBD H. The role of benzylic-allylic hydrogen atoms on the antiradical activity of prenylated natural chalcones: a thermodynamic and kinetic study. Journal of biomolecular structure & dynamics, 2021; 39(6): 1955–1964.

CANO A, et al. State-of-the-art polymeric nanoparticles as promising therapeutic tools against human bacterial infections. Journal of nanobiotechnology, 2020; 18(1).

CHIARADIA LD, et al. Synthesis, biological evaluation, and molecular modeling of chalcone derivatives as potent inhibitors of Mycobacterium tuberculosis protein tyrosine phosphatases (PtpA and PtpB). Journal of medicinal chemistry, 2012; 55(1): 390–402.

DUARTE GD. Preparação e avaliação de atividade antimicrobiana de chalconasheterocíclicas. Dissertação de Mestrado - Universidade Federal da Paraíba, JoãoPessoa,2020; 87p.

FERREIRA NC, et al. Anti-prion activity of a panel of aromatic chemical compounds: In vitro and in silico approaches. PloS one, 2014; 9(1): e84531.

GOMES M, et al. Chalcone derivatives: Promising starting points for drug design. Molecules (Basel, Switzerland), 2017; 22(8): 1210.

HASSAN GS, et al. New pyrazole derivatives: Synthesis, anti-inflammatory activity, cycloxygenase inhibition assay and evaluation of mPGES. European journal of medicinal chemistry, 2019; 171(1): 332–342.

HASSAN MM, FAROUK O. Synthesis and antimicrobial evaluation of some functionalized heterocycles derived from novel quinolinyl chalcone. Journal of heterocyclic chemistry, 2017; 54(6): 3133–3142.

HELMY YA, et al. Antimicrobial resistance and recent alternatives to antibiotics for the control of bacterial pathogens with an emphasis on foodborne pathogens. Antibiotics (Basel, Switzerland), 2023; 12(2): 274.

HORLEY NJ, et al. (E)-3-(3,4,5-Trimethoxyphenyl)-1-(pyridin-4-yl)prop-2-en-1-one, a heterocyclic chalcone is a potent and selective CYP1A1 inhibitor and cancer chemopreventive agent. Bioorganic & medicinal chemistry letters, 2017; 27(24): 5409–5414.

INSUASTY B, et al. Synthesis of 1‐substituted 3‐aryl‐5‐aryl(hetaryl)‐2‐pyrazolines and study of their antitumor activity. Archiv der Pharmazie, 2012; 345(4): 275–286.

JORDA A, ZEITLINGER M. Preclinical pharmacokinetic/pharmacodynamic studies and clinical trials in the drug development process of EMA-approved antibacterial agents: A review. Clinical pharmacokinetics, 2020; 59(9): 1071–1084.

KHAN SA, et al. Microwave assisted synthesis of chalcone and its polycyclic heterocyclic analogues as promising antibacterial agents: In vitro, in silico and DFT studies. Journal of molecular structure, 2019; 1190(1): 77–85.

KRISHNAMURTHIVR, et al. A new analysis method for evaluating bacterial growth with microplate readers. PloS one, 2021; 16(1): e0245205.

LAGU SB, et al. Design, synthesis, and antibacterial and antifungal activities of novel trifluoromethyl and trifluoromethoxy substituted chalcone derivatives. Pharmaceuticals (Basel, Switzerland), 2020; 13(11): 375.

LAL K, et al. Design, synthesis, characterization, antimicrobial evaluation and molecular modeling studies of some dehydroacetic acid-chalcone-1,2,3-triazole hybrids. Bioorganic chemistry, 2018; 77(1): 236–244.

MACHADO C. et al. Heterocyclic chalcone derivatives: Synthesis and biological activity evaluation: PS207. Porto biomedical journal, 2017; 2(5): 225.

MAO Z. et al. Concise synthesis and biological evaluation of chalcone derivatives bearing n-heterocyclic moieties. Heterocycles, 2019; 92(6).

OLIVEIRA JWA, et al. Bactérias gram-negativas multirresistentes: revisão sobre os desafios e demais discussões. Caderno de Publicações Univag, 2021; 0(11).

PAN T, et al. Biotoxicity and bioavailability of hydrophobic organic compounds solubilized in nonionic surfactant micelle phase and cloud point system. Environmental science and pollution research international, 2017; 24(17): 14795–14801.

PRABHUDEVA MG, et al. Amberlyst-15 catalyzed synthesis of novel thiophene–pyrazoline derivatives: spectral and crystallographic characterization and anti-inflammatory and antimicrobial evaluation. Research on chemical intermediates, 2018; 44(11): 6453–6468.

ROA BM, et al. Avaliação do uso da resazurina em teste de suscetibilidade in vitro frente a Sporothrix brasiliensis. VITTALLE - Revista de Ciências da Saúde, 2019; 31(2): 32–37.

SAYED GH, et al. Pyrazole, pyrazolone and enaminonitrile pyrazole derivatives: Synthesis, characterization and potential in corrosion inhibition and antimicrobial applications. Journal of molecular liquids, 2018; 252(1): 329–338.

SHANKARAIAH N, et al. Synthesis of different heterocycles-linked chalcone conjugates as cytotoxic agents and tubulin polymerization inhibitors. Bioorganic & medicinal chemistry, 2017; 25(17): 4805–4816.

TAKATE SJ, et al. Thiazolyl-pyrazole derivatives as potential antimycobacterial agents. Bioorganic & medicinal chemistry letters, 2019; 29(10): 1199–1202.

TANG X, et al. Novel chalcone derivatives containing a 1,2,4-triazine moiety: design, synthesis, antibacterial and antiviral activities. RSC advances, 2019; 9(11): 6011–6020.

VANANGAMUDI G, et al. Synthesis, spectral linearity, antimicrobial, antioxidant and insect antifeedant activities of some 2,5-dimethyl-3-thienyl chalcones. Arabian journal of chemistry, 2017; 10(1): S1254–S1266.

XUE Y. et al. Antiradical activity and mechanism of coumarin–chalcone hybrids: Theoretical insights. The journal of physical chemistry. A, 2018; 122(43): 8520–8529.

ZHAO C, et al. Nitrogen-doped carbon quantum dots as an antimicrobial agent against Staphylococcus for the treatment of infected wounds. Colloids and surfaces. B, Biointerfaces, 2019; 179(1): 17–27.

ŻYSZKA B, et al. Highly effective, regiospecific reduction of chalcone by cyanobacteria leads to the formation of dihydrochalcone: two steps towards natural sweetness. Microbial cell factories, 2017; 16(1).