2403-30-7Relevant articles and documents
On the investigation of hybrid quinones: Synthesis, electrochemical studies and evaluation of trypanocidal activity
Jardim, Guilherme A. M.,Reis, Wallace J.,Ribeiro, Matheus F.,Ottoni, Flaviano M.,Alves, Ricardo J.,Silva, Thaissa L.,Goulart, Marilia O. F.,Braga, Antonio L.,Menna-Barreto, Rubem F. S.,Salom?o, Kelly,De Castro, Solange L.,Da Silva Júnior, Eufranio N.
, p. 78047 - 78060 (2015)
In our continued search for novel trypanocidal compounds, arylamine, chalcone, triazolic, triazole-carbohydrate and chalcogenium derivatives containing a naphthoquinone scaffold were prepared; in addition to electrochemical studies, these compounds were evaluated against the infective bloodstream form of Trypanosoma cruzi, the etiological agent of Chagas disease. Among the thirty-eight compounds herein evaluated, six were found to be more potent against trypomastigotes than the standard drug benznidazole, with IC50/24 h values between 52.9 and 89.5 μM.
Anti-Trichomonas vaginalis activity of chalcone and amino-analogues
Trein, Márcia Rodrigues,Rodrigues e Oliveira, Lígia,Rigo, Graziela Vargas,Garcia, Mayara Aparecida Rocha,Petro-Silveira, Brenda,da Silva Trentin, Danielle,Macedo, Alexandre José,Regasini, Luis Octávio,Tasca, Tiana
, p. 607 - 615 (2019)
Trichomoniasis is the most common non-viral sexually transmitted disease worldwide and can lead to serious consequences in reproductive health, cancer, and HIV acquisition. The current approved treatment present adverse effects and drug resistance data on this neglected parasitic infection is underestimated. Chalcones are a family of molecules that present biological applications, such as activity against many pathogenic organisms including protozoan pathogens. Chalcone (1) and three amino-analogues (2–4) were synthesized by Claisen–Schmidt condensation reaction and had their activity evaluated against the parasitic protozoan Trichomonas vaginalis. This bioassay indicated the presence and position of the amino group on ring A was crucial for anti-T. vaginalis activity. Among these, 3′-aminochalcone (3) presented the most potent effect and showed high cytotoxicity against human vaginal cells. On the other hand, 3 was not able to exhibit toxicity against Galleria mellonella larvae, as well as the hemolytic effect on human erythrocytes. Trophozoites of T. vaginalis were treated with 3, and did not present significant reactive oxygen species (ROS) accumulation, but induced a significantly higher ROS accumulation in human neutrophils after co-incubation. T. vaginalis pyruvate:ferredoxin oxidoreductase (PFOR) and β-tubulin gene expression was not affected by 3.
Design and synthesis of novel anti-inflammatory/anti-ulcer hybrid molecules with antioxidant activity
Balaini, Ajitesh,Bali, Alka,Chaudhari, Bhim Bahadur
, p. 994 - 1006 (2021/11/30)
Background: NSAIDs are the most widely prescribed medications worldwide for their anti-inflammatory, antipyretic, and analgesic effects. However, their chronic use can lead to several adverse drug events including GI toxicity. The selective COX-2 inhibitors developed as gastro-sparing NSAIDs also suffer from serious adverse effects which limit their efficacy. Objective: Local generation of reactive oxygen species is implicated in NSAID-mediated gastric ul-ceration and their combination with H2 antagonists like famotidine reduces the risk of ulcers. The objective of this work was to design and synthesize novel methanesulphonamido isoxazole derivatives by hybridizing the structural features of NSAIDs with those of antiulcer drugs (ranitidine, fa-motidine, etc.) to utilize a dual combination of anti-inflammatory activity and reducing (antioxidant) potential. Methods: The designing process utilized three dimensional similarity studies and utilized an isoxa-zole core having a potential for anti-inflammatory as well as radical scavenging antioxidant activity. The compounds were assayed for their anti-inflammatory activity in established in vivo models. The in vitro antioxidant activity was assessed in potassium ferricyanide reducing power (PFRAP) assay employing ascorbic acid as the standard drug. Results: Compounds 5, 6, 9 and 10 showed anti-inflammatory activity comparable to the standard drugs and were also found to be non-ulcerogenic at the test doses. Compounds 6-10 exhibited good antioxidant effect in the concentration range of 1.0-50.0 μmol/ml. The test compounds were also found to comply with the Lipinski rule suggesting good oral absorption. Conclusion: A new series of isoxazole based compounds is being reported with good anti-inflammatory activity coupled with antioxidant potential as gastro-sparing anti-inflammatory agents.
A combined experimental and DFT investigation of mono azo thiobarbituric acid based chalcone disperse dyes
El-Sadany, Samir K.,El-atawy, Mohamed A.,Hamed, Ezzat A.,Mahmoud, Mona N.,Omar, Alaa Z.
, (2020/10/08)
A number of monoazo dyes were synthesized by the reaction of 4-aminoacetophenone with different substituted benzaldehydes to give a new series of chalcone derivatives. The diazonium salts of these chalcones then allowed to react with thiobarbituric acid to produce the appropriate azo dye. The structures of the newly synthesized dyes were assigned by IR, NMR spectral data. IR study confirmed the existence of azo-dioxothioxo tautomer in the solid phase while 1H NMR study indicated the predominance of azoenol-oxothioxo or hydrazo-dioxothioxo tautomers. The geometries of the azo and hydrazo tautomeric forms and their electronic absorption of the dyes were optimized at B3LYP/6-311G level of theory. All the azo compounds were evaluated for their dyeing performance on polyester fibers, and PET. All the synthesized dyes gave moderate to excellent fastness properties on PET fiber. The effects of the nature of the substituents on the color and dyeing properties of these dyes have been evaluated. The mechanism of dyeing polyester fiber was discussed.
Design, synthesis and antibacterial activity of chalcones against MSSA and MRSA planktonic cells and biofilms
Garcia, Mayara A.R.,Theodoro, Reinaldo S.,Sardi, Janaina C.O.,Santos, Mariana B.,Ayusso, Gabriela M.,Pavan, Fernando R.,Costa, Alan R.,Santa Cruz, Lucas M.,Rosalen, Pedro L.,Regasini, Luis O.
, (2021/09/14)
Staphylococcus aureus is the one of the most successful modern pathogens. The same bacterium that lives as a skin and mucosal commensal can be transmitted in health-care and community-settings and causes severe infections. Thus, there is a great challenge for a discovery of novel anti-Staphylococcus aureus compounds, which should act against resistant strains. Herein, we designed and synthesized a series of 17 chalcones, substituted by amino group on ring A, which were evaluated against methicillin-susceptible S. aureus (MSSA) and methicillin-resistant S. aureus MRSA planktonic cells. The antibacterial potency was improved by substituents on ring B, which were designed according to Topliss’ manual method. 4-bromo-3′-aminochalcone (5f) was the most active, demonstrating minimum inhibitory concentration (MIC) values of 1.9 μg mL?1 and 7.8 μg mL?1 against MSSA and MRSA, respectively. The association of 5f with vancomycin demonstrated synergistic effect against MSSA and MRSA, with Fractional Inhibitory Concentration Index (FICI) values of 0.4 and 0.3, respectively. Subinhibitory concentration of 5f inhibited the MSSA and MRSA adhesion to human keratinocytes. Chalcone 5f was able to reduce MSSA and MRSA biofilm formation, as well as acts on preformed biofilm in concentration-dependent mode. Scanning electron microscopy analyses confirmed severe perturbations caused by 5f on MSSA and MRSA biofilm architecture. The acute toxicity assay, using Galleria mellonella larvae, indicated a low toxic effect of 5f after 72 h, displaying lethality of 20% and 30% at 7.8 μg mL?1 and 78.0 μg mL?1, respectively. In addition, the antibacterial activity spectrum of 5f indicated action against planktonic cells of Enterococcus faecalis (MIC = 7.8 μg mL?1), Acinetobacter baumannii (MIC = 15.6 μg mL?1) and Mycobacterium tuberculosis (MIC = 5.7 μg mL?1). Altogether, these results open new avenues for 5f as an anti-Staphylococcus aureus agent, with potential applications as antibacterial drug, adjunct of antibiotics and medical devices coating.
