2875-22-1Relevant academic research and scientific papers
Thallium(III) p-tosylate-mediated oxidative [1,2] rearrangement of 2-naphthyl and 2-heteroarylchromanones
Kurapati, Chidvilas,Muthukrishnan, Murugan,Singh, Om V.,Gundla, Rambabu
supporting information, p. 172 - 177 (2021/10/29)
A practical and effective approach towards the synthesis of 3-heteroaryl-4H-chromen-4-ones by the oxidative [1,2] rearrangement of the respective 2-heteroaryl chroman-4-ones using thallium(III) p-tosylate is presented. The oxidative rearrangement of α- an
Design, synthesis and structural confirmation of a series of 2-(thiophen-2-yl)- 4h-chromen-3-yl-sulfonate derivatives and preliminary investigation of their antioxidant and anticancer potentials
Bu, Ming,Han, Lu,Lv, Zhen,Yang, Jifang,Zang, Jialin
, p. 1780 - 1788 (2021/08/05)
A series of novel 2-(thiophen-2-yl)-4H-chromen-3-yl-sulfonate derivatives (4a-4n) were synthesized and investigated for their in vitro free radical scavenging potential as well as cytotoxic efficacies against selected cancer cell lines. The cytotoxicity of the 4H-chromene derivatives (4a-4n) was evaluated according to three human cancer cell lines (HepG2, A549, HeLa) by utilizing a 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. Accordingly, part of the results exhibited better cytotoxic activities than that of the positive controls (4H-chromen-4-one and apigenin). Among them, compounds 4c-4g exhibited better training to the positive control against the three human cancer cell lines (half maximal inhibitory concentration (IC50) = 3.87 ± 0.12 to 21.38 ± 0.52 μM). Moreover, the extract of the 4H-chromene derivatives (4a-4n) showed better activity against 2,2-diphenyl-1-picrylhydrazyl (DPPH) and 2,2'-azino-bis-3-ethylbenzothiazoline- 6-sulfonic acid (ABTS) in antioxidant assays compared to that of the positive control ascorbic acid (IC50 = 12.72 ± 0.27, 5.09 ± 0.21 μg mL-1). Thus, it can be confirmed from the bioassay results that the overall structural design, as well as proper substitution, is crucial in delivering anticipated biological effects. In this regard, spectroscopic techniques such as 1H nuclear magnetic resonance (NMR), 13C NMR, and high-resolution mass spectrometry (HRMS) were also carried out to confirm the final structures.
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.
Structural and spectroscopic analysis and evaluation of cytotoxic activity of 2-hydroxychalcones against human cancer cell lines
Almeida-Neto, Francisco W. Q.,Bandeira, Paulo N.,Barreto, Ant?nio C. H.,Barros-Nepomuceno, Francisco W. A.,Juli?o, Murilo S. S.,Leal, Antonio L. A. B.,Marinho, Emmanuel S.,Pessoa, Claudia,Pinheiro, Daniel P.,Teixeira, Alexandre M. R.,da Silva, Priscila T.,de Lima-Neto, Pedro,de Paiva, Aldeneide S.,dos Santos, Hélcio S.
, (2021/07/28)
Chalcones and their derivatives exhibit a broad spectrum of pharmacological activities, including antiproliferative activities. Accordingly, they are deemed robust anticancer candidates for cytotoxicity assays. Herein, we synthesized and characterized fou
Antischistosomal properties of aurone derivatives against juvenile and adult worms of Schistosoma mansoni
Pereira, Vinicius R.D.,da Silveira, Lígia S.,Mengarda, Ana C.,Alves Júnior, Ismael J.,da Silva, Ohana Oliveira Zuza,Miguel, Fábio Balbino,Silva, Marcos P.,Almeida, Ayla das C.,Torres, Daniel da Silva,Pinto, Priscila de F.,Coimbra, Elaine S.,de Moraes, Josué,Couri, Mara R.C.,da Silva Filho, Ademar A.
, (2020/11/17)
Schistosomiasis is a neglected disease caused by helminth flatworms of the genus Schistosoma, affecting over 240 million people in more than 70 countries. The treatment relies on a single drug, praziquantel, making urgent the discovery of new compounds. A
Exploring 3-hydroxyflavone scaffolds as mushroom tyrosinase inhibitors: synthesis, X-ray crystallography, antimicrobial, fluorescence behaviour, structure-activity relationship and molecular modelling studies
Ashraf, Jamshaid,Mughal, Ehsan Ullah,Sadiq, Amina,Bibi, Maryam,Naeem, Nafeesa,Ali, Anser,Massadaq, Anam,Fatima, Nighat,Javid, Asif,Zafar, Muhammad Naveed,Khan, Bilal Ahmad,Nazar, Muhammad Faizan,Mumtaz, Amara,Tahir, Muhammad Nawaz,Mirzaei, Masoud
, p. 7107 - 7122 (2020/08/21)
To explore new scaffolds as tyrosinase enzyme inhibitors remain an interesting goal in the drug discovery and development. In due course and our approach to synthesize bioactive compounds, a series of varyingly substituted 3-hydroxyflavone derivatives (1-23) were synthesized in one-pot reaction and screened for in?vitro against mushroom tyrosinase enzyme. The structures of newly synthesized compounds were unambiguously corroborated by usual spectroscopic techniques (FTIR, UV-Vis, 1H-, 13C-NMR) and mass spectrometry (EI-MS). The structure of compound 15 was also characterized by X-ray diffraction analysis. Furthermore, the synthesized compounds (1-23) were evaluated for their antimicrobial potential. Biological studies exhibit pretty good activity against most of the bacterial-fungal strains and their activity is comparable to those of commercially available antibiotics i.e. Cefixime and Clotrimazole. Amongst the series, the compounds 2, 4, 5, 6, 7, 10, 11, 14 and 22 exhibited excellent inhibitory activity against tyrosinase, even better than standard compound. Remarkably, the compound 2 (IC50 = 0.280 ± 0.010 μg/ml) was found almost sixfold and derivative 5 (IC50 = 0.230 ± 0.020 μg/ml) about sevenfold more active as compared to standard Kojic acid (IC50 =1.79 ± 0.6 μg/ml). Moreover, these synthetic compounds (1-23) displayed good to moderate activities against tested bacterial and fungal strains. Their emission behavior was also investigated in order to know their potential as fluorescent probes. The molecular modelling simulations were also performed to explore their binding interactions with active sites of the tyrosinase enzyme. Limited structure-activity relationship was established to design and develop new tyrosinase inhibitors by employing 2-arylchromone as a structural core in the future. Communicated by Ramaswamy H. Sarma.
Substituent-Controlled Divergent Cascade Cycloaddition Reactions of Chalcones and Arylalkynols: Access to Spiroketals and Oxa-Bridged Fused Heterocycles
Chang, Weixing,Kong, Jingyang,Li, Jing,Liu, Lingyan,Wang, Hongkai,Zeng, Tianlong
supporting information, p. 4024 - 4032 (2021/07/12)
Herein, we report substituent-controlled divergent cascade cycloaddition reactions of chalcones and arylalkynols in the presence of PtI2. Depending on the substituent on the chalcone, either spiroketals or oxa-bridged fused heterocycles could be obtained in the ranges of 86–97% and 87–95% yields under identical reaction conditions. Control experiments were carried out to elucidate the origin of the high chemoselectivity. These provide a method for the synthesis of a diverse array of structurally complex oxygen-containing heterocycles. (Figure presented.).
Glycolytic inhibition and antidiabetic activity on synthesized flavanone scaffolds with computer aided drug designing tools
Kiruthiga, Natarajan,Saravanan, Govindaraj,Selvinthanuja, Chellappa,Sivakumar, Thangavel,Srinivasan, Kulandaivel
, p. 574 - 592 (2021/09/30)
Background: Diabetes mellitus is a challengeable metabolic disorder that leads to a group of complications when the HbA1c level is not maintained. Most of the existing drugs avail-able in the market in long-term use may lead to serious adverse effects. He
A novel one-pot synthesis of flavones
Chang, Meng-Yang,Tsai, Min-Chen,Lin, Chun-Yi
, p. 11655 - 11662 (2021/03/31)
In this paper, a one-pot facile route for the BiCl3/RuCl3-mediated synthesis of functionalized flavones is described, including: (i) intermolecularortho-acylation of substituted phenols with cinnamoyl chlorides, and (ii) intramolecular cyclodehydrogenation of the resultingo-hydroxychalcones. The reaction conditions are discussed herein.
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).
