127089-57-0Relevant academic research and scientific papers
Spectroscopic analysis by NMR, FT-Raman, ATR-FTIR, and UV-Vis, evaluation of antimicrobial activity, and in silico studies of chalcones derived from 2-hydroxyacetophenone
Xavier, Jayze da Cunha,de Almeida-Neto, Francisco W.Q.,Rocha, Janaína E.,Freitas, Thiago S.,Freitas, Priscila R.,de Araújo, Ana C.J.,da Silva, Priscila T.,Nogueira, Carlos E.S.,Bandeira, Paulo N.,Marinho, Márcia M.,Marinho, Emmanuel S.,Kumar, Nitin,Barreto, Ant?nio C.H.,Coutinho, Henrique D.M.,Juli?o, Murilo S.S.,dos Santos, Hélcio S.,Teixeira, Alexandre M.R.
, (2021)
Six 2’-hydroxychalcones were synthesized and characterized by NMR, FT-Raman, ATR-FTIR, and UV-Vis. These chalcones alone and in combination with the ciprofloxacin, penicillin, and erythromycin antibiotics were tested against multiresistant strains of Staphylococcus aureus. It was also verified by in vitro and in silico studeis the capacity of these chalcones to inhibit the NorA efflux pump. The MICs values of ciprofloxacin were reduced in the presence of all tested chalcones. For norfloxacin antibiotic, the chalcones A1, A4, A5 and A6 promoted the reduced in the MIC values. The A2 chalcone was the only one to reduce the MIC values when associated with penicillin. Any chalcones were not able to reduce MIC values when associated with erythromycin. These results indicate that the synergistic effects demonstrated for the synthesized chalcones were influenced by the introduction of a furanic ring (A1), a chlorine atom and a methoxy group at the C4 position (A2 and A4), a second double bond (A5), and a fluorine atom at the C2 position (A6). The ADMET analysis predicts that the chalcones A2, A3, A5 and A6 have easier cell permeation. The nucleophilic region makes the A5 chalcone capable of covalently bonding with plasma proteins, and the presence of oxygenated aromatic substitutions makes the chalcones A1 and A4 more water-soluble and consequently easier to excrete. On the other hand, the substitution of the methoxy group of the A4 chalcone makes it more susceptible to O-demethylation reactions by the CYP3A4 isoenzyme. The molecular docking revealed that all six chalcones could hinder the binding of norfloxacin to the NorA efflux pump.
Effect of solvent polarity on the photophysical properties of chalcone derivatives
Kumari, Rekha,Varghese, Anitha,George, Louis,Sudhakar
, p. 24204 - 24214 (2017)
The absorption and fluorescence characteristics of (E)-3-(furan-2-yl)-1-(4-nitrophenyl)prop-2-en-1-one (FNPO), (E)-1-(4-aminophenyl)-3-(furan-2-yl)prop-2-en-1-one (AFPO) and (E)-3-(furan-2-yl)-1-(2-hydroxyphenyl)prop-2-en-1-one (FHPO) were recorded in eig
A facile one pot microwave- assisted solid phase synthesis of 2-amino-4,6-diaryl pyrimidines and their antibacterial activity
Jhala, Yajuvendra S.,Gahlot,Dulawat, Shiv S.,Verma
, p. 253 - 258 (2006)
An environmentally benign, manipulatively simple & rapid method for the synthesis of 2-amino-4, 6-diaryl pyrimidines (4a-f) from corresponding chalcones (3a-f) & guanidine nitrate using basic alumina under solvent free dry condition and microwave irradiat
Convenient synthesis of flavanone derivatives via oxa-Michael addition using catalytic amount of aqueous cesium fluoride
Miura, Motofumi,Shigematsu, Karin,Toriyama, Masaharu,Motohashi, Shigeyasu
supporting information, (2021/10/25)
A total of 36 flavanones, which included polycyclic aromatic and heterocyclic rings, were readily synthesized via oxa-Michael addition from the corresponding hydroxychalcones with a catalytic amount of aqueous cesium fluoride solution under mild conditions. This method could be applied to the scalable synthesis of eriodictyol as a known potent inhibitor of the SARS-CoV-2 spike protein.
Synthetic Aurones: New Features for Schistosoma mansoni Therapy
Alves da Silva Filho, Ademar,Alves de Oliveira, Bruna,Azevedo Alves, Lara,Fortini Grenfell e Queiroz, Rafaella,Gomes Vasconcelos, Eveline,Paulo da Silva, Marcos,Silva Torres, Daniel,Vanessa Zabala Capriles Goliatt, Priscila,de Faria Pinto, Priscila,Carius de Souza, Vinícius,Martins Parreiras, Patrícia,Moraes, Josué,Rúbia Costa Couri, Mara,Roberto Silva, Márcio,Rodrigues Dur?es Pereira, Vinícius,Souza d Silveira, Lígia
, (2021/10/23)
In this work, two synthetic aurones revealed moderate schistosomicidal potential in in vitro and in vivo assays. Aurones (1) and (2) promoted changes in tegument integrity and motor activity, leading to death of adult Schistosoma mansoni worms in in vitro
Biocatalytic green alternative to existing hazardous reaction media: Synthesis of chalcone and flavone derivatives via the Claisen-Schmidt reaction at room temperature
Tamuli, Kashyap J.,Sahoo, Ranjan K.,Bordoloi, Manobjyoti
supporting information, p. 20956 - 20965 (2020/12/31)
Owing to the increasing amount of waste materials around the globe, the conversion of waste or secondary by-products to value-added products for various applications has gained significant interest. Herein, two novel agro-food waste products, Musa sp. 'Malbhog' peel ash (MMPA) and Musa Champa Hort. ex Hook. F. peel ash (MCPA) are used as catalysts to promote an inexpensive, efficient and eco-friendly carbon-carbon bond forming crossed aldol reaction at room temperature in solvent free conditions. Furthermore, the resulting products were subjected to reactions with these promoters in an oxygen atmosphere and led to the formation of novel flavone derivatives. Moreover, the used catalysts were properly characterized using different sophisticated analytical techniques such as Fourier-transform infrared spectroscopy (FT-IR), X-ray diffractometry (XRD), Brunauer-Emmett-Teller analysis (BET), Raman spectroscopy, scanning electron microscopy energy dispersive X-ray spectroscopy (SEM-EDS), transition electron microscopy (TEM), X-ray photoelectron spectroscopy (XPS) and thermogravimetric analysis (TGA) along with element detection using atomic absorption spectroscopy and ion chromatographic methods. These two approaches are metal free, as well as being devoid of any extra additives, co-catalysts, harsh conditions, the use of column chromatography for purification and result in a higher yield of the product within a short space of time. The catalytic abilities of the promoter were also examined to synthesize important bioactive molecules such as butein and apigenin at room temperature. With gram scale synthesis of the chalcone derivatives, the used catalysts (MMPA and MCPA) were further reused for five cycles and did not demonstrate any loss in catalytic activity.
Synthesis and antibacterial activity of chalcone derivatives containing thioether triazole
Chen, Mei,Chen, Ying,He, Jun,He, Ming,Li, Pu,Su, Shijun,Wang, Hua,Xue, Wei
, (2020/01/22)
The infection of Xanthomonas oryzae pv. Oryzae (Xoo), Ralstonia solanacearum (Rs), and Xanthomonas axonopodis pv. Citri (Xac) has become a major problem in agricultural production. In this study, a series of novel chalcone derivatives containing thioether triazoles were designed and synthesized. The structures of the novel compounds were systematically characterized via 1H-NMR, 13C-NMR, and HRMS. Moreover, the antibacterial activity results showed that E10, E11, E15, and E16 have adequate antibacterial activities against Xoo, Rs, and Xac. Among the different compounds, E15 exhibited remarkable inhibitory effect against Xac with an EC50 of 9.1 μg.mL-1, which was better than that of commercial agent bismerthiazol (54.9 μg.mL-1). In addition, the possible antibacterial mechanism of the target compound E15 against Xac was studied via scanning electron microscopy (SEM).
Novel chalcone and flavone derivatives as selective and dual inhibitors of the transport proteins ABCB1 and ABCG2
Silbermann, Katja,Shah, Chetan P.,Sahu, Niteshkumar U.,Juvale, Kapil,Stefan, Sven Marcel,Kharkar, Prashant S.,Wiese, Michael
, p. 193 - 213 (2019/01/03)
During cancer chemotherapy, certain cancers may become cross-resistant to structurally diverse antineoplastic agents. This so-called multidrug resistance (MDR) is highly associated with the overexpression of ATP-binding cassette (ABC) transport proteins. These membrane-bound efflux pumps export a broad range of structurally diverse endo- and xenobiotics, including chemically unrelated anticancer agents. This translocation of drugs from the inside to the outside of cancer cells is mediated at the expense of ATP. In the last 40 years, three ABC transporters – ABCB1 (P-gp), ABCC1 (MRP1), and ABCG2 (BCRP) – have mainly been attributed to the occurrence of MDR in cancer cells. One of the strategies to overcome MDR is to inhibit the efflux transporter function by small-molecule inhibitors. In this work, we investigated new chalcone- and flavone-based compounds for selective as well as broad-spectrum inhibition of the stated transport proteins. These include substituted chalcones with variations at rings A and B, and flavones with acetamido linker at position 3. The synthesized molecules were evaluated for their inhibitory potential against ABCB1, ABCC1, and ABCG2 in calcein AM and pheophorbide A assays. In further investigations with the most promising candidates from each class, we proved that ABCB1- and ABCG2-mediated MDR could be reversed by the compounds. Moreover, their intrinsic toxicity was found to be negligible in most cases. Altogether, our findings contribute to the understanding of ABC transport proteins and reveal new compounds for ongoing evaluation in the field of ABC transporter-mediated MDR.
Design, synthesis, and biological evaluation of Helicobacter pylori inosine 5′-monophosphate dehydrogenase (HpIMPDH) inhibitors
Sahu, Niteshkumar U.,Purushothaman, Gayathri,Thiruvenkatam, Vijay,Kharkar, Prashant S.
, p. 125 - 132 (2018/11/06)
Inosine 5′-monophosphate dehydrogenase (IMPDH) catalyzes a crucial step in the biosynthesis of guanine nucleotides. Being a validated target for immunosuppressive, antiviral, and anticancer drug development, lately it has been exploited as a promising target for antimicrobial therapy. Extending our previous work on Mycobacterium tuberculosis IMPDH, GuaB2, inhibitor development, we screened a set of 23 new chemical entities (NCEs) with substituted flavone (Series 1) and 1,2,3-triazole (Series 2) core structures for their in vitro Helicobacter pylori IMPDH (HpIMPDH) and human IMPDH2 (hIMPDH2) inhibitory activities. All the NCEs possessed acceptable molecular, physicochemical, and toxicity property profiles. The ranges for HpIMPDH and hIMPDH2 inhibition were 9–99.9% and 16–57%, respectively, at 10 μM concentration. The most potent HpIMPDH inhibitor, 25c, exhibited IC50 value of 1.27 μM with no hIMPDH2 inhibitory activity. The moderately potent, structurally novel hit molecule, 25c, may serve as a lead for further design and development of highly potent HpIMPDH inhibitors.
Synthesis of a series of chalcones and related flavones and evaluation of their antibacterial and antifungal activities
Benouda, Hind,Bouchal, Btissam,Challioui, Allal,Oulmidi, Abdelkader,Harit, Tarik,Malek, Fouad,Riahi, Abdelkhalek,Bellaoui, Mohammed,Bouammali, Boufelja
, p. 93 - 100 (2019/01/04)
Background: A series of chalcones and flavones were synthesized from 2’-hydroxyacetophenone and substituted aromatic aldehydes via Simmons-Schmidt condensation followed by oxidative cyclization. Methods: Characterization of the obtained structures was established on the basis of their spectroscopic data. The synthesized compounds were screened for their antimicrobial activities against five bacterial strains (Citrobacter freundii, Staphylococcus aureus, Listeria monocytogenes, Salmonella braenderup, Escherichia coli.) and two fungal strains (Candida albicans, Candida krusei). Results: The in vitro bioassay results indicated that some target compounds displayed moderate (4d, 4e) to high (4a) antifungal activity against the pathogenic fungi C. albicans and C. krusei. Conclusion: For the antibacterial activity, only products 3d and 4d showed a weak antibacterial activity. These compounds can lead to the design of new drugs with specific antifungal activity.
