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

Abstract

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.

Synthesis and antibacterial activity of novel 1,4‐pentadien‐3‐one derivatives bearing a benzothiazole moiety

“…[10] As an important curcumin analogue, penta-1,4-dien-3-ones put up better stability than curcumin, as well as indicating low toxic effects on plants and human health. Penta-1,4-dien-3-ones have contributed greatly to drug discovery over the years, which possess antimicrobial, [19][20][21][22][23][24] antiviral, [25][26][27][28] anticancer, [29][30][31] and anti-inflammatory properties. [32,33] There were various penta-1,4-dien-3-ones derivatives were reported by us recently, and which exhibited remarkable antibacterial activities.…”

“…[32,33] There were various penta-1,4-dien-3-ones derivatives were reported by us recently, and which exhibited remarkable antibacterial activities. Which bearing a benzotriazin-4(3H)-one moiety indicated considerable bioactivities against Xac and Rs with EC 50 values of 22.45 and 34.77 μg ml À1 , [32,33] respectively; containing a phosphite ester fragment exhibited significant bioactivities against Xoo with EC 50 value of 8.6 μg ml À1 ; [21] connecting with a thiophene sulfonate group exerted significant bioactivity against Xac with EC 50 value of 11.0 μg ml À1 , [22] joining together with a triazine scaffolds exerted significant bioactivity against Xac with EC 50 value of 0.4 μg ml À1 , [23] and combining with a 1,2,4-triazole scaffolds exerted significant bioactivity against Xac with EC 50 value of 5.4 μg ml À1 and toward Xoo with EC 50 value of 10.9 μg ml À1 . [24] Based on mentioned above and active splicing principle, we attempted to introduce more substituents to synthesize more compounds that based on benzothiazole and penta-1, 4-dien-3-ones.…”

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

“…citri , Ralstonia solanacearum and Xanthomonas oryzae pv. oryzae , respectively [1–3] . These bacteria are very serious and hard to manage effectively in agricultural production.…”