Novel chalcone derivatives containing a 1,2,4-triazine moiety: design, synthesis, antibacterial and antiviral activities

Xu, Tao; Su, Shijun; Chen, Mei; He, Jun; Xia, Rongjiao; Guo, Tao; Chen, Ying; Zhang, Cheng; Wang, Jun

doi:10.1039/c9ra00618d

Cited by 68 publications

(53 citation statements)

References 43 publications

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“…According to previously reported methods (Chen et al, 2019;Tang et al, 2019;Gan et al, 2017), intermediates 1 and 2 could be obtained. Using benzyl, biacetyl and thio-semicarbazide as the initial materials in acetic acid and water was stirred at 100−110 • C for 6-8 h to obtain the intermediate 3 (Tang et al, 2019). (10 mmol) and K 2 CO 3 (30 mmol) in dimethylformamide and stirred at room temperature for 6-8 h. After the reaction was completed (monitored by TLC), the mixture was extracted with ethyl acetate (30 mL × 3).…”

Section: Instruments and Chemicalsmentioning

confidence: 90%

“…citri (Xac), Xanthomonas oryzaepv. oryzae (Xoo) and Ralstonia solanacearum (R.s) were evaluated at 100 µg/mL using a turbidimeter (Tang et al, 2019;Zhang et al, 2018). This test method is provided in the Supplemental Information.…”

Section: Antibacterial Activity In Vitromentioning

confidence: 99%

“…Using N. tabacun L. leaves under the same age as that of test subjects, the curative, protective and inactivation activities against TMV (in vivo) at a concentration of 500 µg/mL were evaluated by the half-leaf blight spot method (Chen et al, 2019).This test method is provided in the Supplemental Information.…”

Section: Antiviral Activities In Vivomentioning

confidence: 99%

“…The antibacterial activities of target compounds have been evaluated by the turbidimeter test (Zhang et al, 2018;Tang et al, 2019). Results in Table 1 indicated that some of synthesized compounds exhibited appreciable antibacterial activities against Xoo, R.s and Xac at the concentrates of 100 µg/mL.…”

Section: Antibacterial Activities In Vitromentioning

confidence: 99%

“…In addition, triazine scaffold has been associated with diversified pharmacological activities (Irannejad et al, 2010), such as antioxidant (Khoshneviszadeh et al, 2016), antithrombotic (Tamboli et al, 2015) antiplatelet (Konno et al, 1993), anticancer (Fu et al, 2017, thromboxane synthetase inhibition (Monge et al, 2010), antimalarial (Ban et al, 2010, α-glucosidase inhibition , antiviral and antibacterial activities (Tang et al, 2019). Recently, it was found that the heterocyclic nitrogen of the triazine derivatives had tremendous applications in the development of novel agricultural bactericides and virucides (Zhang et al, 2018).…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and biological activity of 1,4-pentadien-3-one derivatives containing triazine scaffolds

Chen

et al. 2020

PeerJ Organic Chemistry

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Background. Literatures revealed that 1,4-pentadien-3-one and triazine derivatives exhibited a wide variety of biological activities. In order to develop highly bioactive molecules, in this study, a series of novel 1,4-pentadien-3-one derivatives containing triazine moieties were synthesized and their antibacterial and antiviral activities were investigated. Methods. A series of novel 1,4-pentadien-3-one derivatives containing triazine moieties were synthesized and characterized in detail via 1 H NMR, 13 C NMR and HRMS spectra. The antibacterial activities against Xanthomonas axonopodispv. citri (Xac), Xanthomonas oryzaepv. oryzae (Xoo) and Ralstonia solanacearum (R.s) were evaluated at 100 and 50 µg/mL using a turbidimeter and N. tabacun L. leaves under the same age as that of test subjects. The curative, protective and inactivation activities against tobacco mosaic virus (TMV) at a concentration of 500 µg/mL were evaluated via the half-leaf blight spot method. Results. The bioassay results showed that some of the target compounds exhibited fine antibacterial activities against Xac and R.s. Particularly, half maximal effective concentration (EC 50 ) values of some target compounds against R.s are visibly better than that of the positive control bismerthiazol (BT). Notably, compound 4a showed excellent inactivation activity against TMV with a EC 50 value of 12.5 µg/mL, which was superior to that of ningnanmycin (NNM,13.5 µg/mL). Besides, molecular docking studies for 4a with tobacco mosaic virus coat protein (TMV-CP) showed that the compound was embedded well in the pocket between the two subunits of TMV-CP. These findings indicate that 1,4-pentadien-3-one derivatives containing triazine moieties may be potential antiviral and antibacterial agents. JB. 2010. 3-Alkylthio-1,2,4-triazine dimers with potent antimalarial activity. Mekuriab EA, Rakotondraibeb LH. 2015. A new class of hybrid anticancer agents inspired by the synergistic effects of curcumin and genistein: design, synthesis, and anti-proliferative evaluation. Cono VL, Yakimov MM, Molinaro A, Silipo A. 2017. The deep-sea polyextremophile halobacteroideslacunaris tb21 rough-type lps: structure and inhibitory activity towards toxic lps. Marine Drugs 15:201 YB. 2017. Design and synthesis of formononetin-dithiocarbamate hybrids that inhibit growth and migration of pc-3Â cells via mapk/wnt signaling pathways. European Journal of Song BA. 2017. Novel trans-ferulic acid derivatives containing a chalcone moiety as potential activator for plant resistance induction.

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Section: Instruments and Chemicalsmentioning

confidence: 90%

Section: Antibacterial Activity In Vitromentioning

confidence: 99%

Section: Antiviral Activities In Vivomentioning

confidence: 99%

Section: Antibacterial Activities In Vitromentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis and biological activity of 1,4-pentadien-3-one derivatives containing triazine scaffolds

Chen

et al. 2020

PeerJ Organic Chemistry

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Chalcone hybrids and their antimalarial activity

Cheng

Yang

Huang

et al. 2020

Archiv der Pharmazie

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Malaria, one of the most striking, re‐emerging infectious diseases caused by the genus Plasmodium, places a huge burden on global healthcare systems. A major challenge in the control and eradication of malaria is the continuous emergence of increasingly widespread drug‐resistant malaria, creating an urgent need to develop novel antimalarial agents. Chalcone derivatives are ubiquitous in nature and have become indispensable units in medicinal chemistry applications due to their diverse biological profiles. Many chalcone derivatives demonstrate potential in vitro and in vivo antimalarial activity, so chalcone could be a useful template for the development of novel antimalarial agents. This review covers the recent development of chalcone hybrids as antimalarial agents. The critical aspects of the design and structure–activity relationship of these compounds are also discussed.

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Design, Synthesis and Antibacterial Activity of Novel Pyrimidine‐Containing 4H‐Chromen‐4‐One Derivatives**

Chen

Tang

et al. 2021

Chemistry & Biodiversity

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A series of pyrimidine-containing 4H-chromen-4-one derivatives were designed and synthesized by combining bioactive substructures. All compounds were characterized using 1 H NMR, 13 C NMR, 19 F NMR and HRMS. Preliminary biological activity results showed that most of title compounds displayed signi cant inhibitory activity against Xanthomonas axonopodis pv. Citri (Xac), Xanthomonas oryzae pv. oryzae (Xoo) and Ralstonia solanacearum (Rs). In particular, compound 4c demonstrated a good inhibitory effect against Xac and Xoo, with half-maximal effective concentration(EC 50 ) values of 15.5 and 14.9 μg/mL respectively, and that of compound 4h showed the best antibacterial activity against Rs with an EC 50 value of 14.7 μg/mL, These results were better than both bismerthiazol (BT, 51.7, 70.1 and 52.7 μg/mL, respectively) and thiodiazole copper (TC, 77.9, 95.8 and 72.1 μg/mL respectively). In vivo antibacterial activity results indicated that compound 4c displayed better curative(42.4%) and protective (49.2%) activities for reducing rice bacterial leaf blight than both BT (35.2, 39.1%) and TC (30.8, 27.3%). The mechanism of compound 4c against Xoo was analysed through scanning electron microscopy (SEM). Results showed that the compound destroied the bacterial cell membrane structure. These results indicated that pyrimidine-containing 4H-chromen-4-one derivatives are valuable in the research of new agrochemicals.

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Novel chalcone derivatives containing a 1,2,4-triazine moiety: design, synthesis, antibacterial and antiviral activities

Abstract: A series of novel chalcone derivatives containing the 1,2,4-triazine moiety were synthesized and their structures were confirmed by 1H NMR, 13C NMR and elemental analyses.

Cited by 68 publications

References 43 publications

Synthesis and biological activity of 1,4-pentadien-3-one derivatives containing triazine scaffolds

Synthesis and biological activity of 1,4-pentadien-3-one derivatives containing triazine scaffolds

Chalcone hybrids and their antimalarial activity

Design, Synthesis and Antibacterial Activity of Novel Pyrimidine‐Containing 4H‐Chromen‐4‐One Derivatives**

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