Synthesis of New N -Acyl-1,2,3-triazole Chalcones and Determination of Their Antibacterial Activity
- PDF / 272,594 Bytes
- 4 Pages / 612 x 792 pts (letter) Page_size
- 86 Downloads / 180 Views
TRY
Synthesis of New N-Acyl-1,2,3-triazole Chalcones and Determination of Their Antibacterial Activity I. S. Odina, S. Caob, D. Hughesb, E. V. Zamaratskiic, Yu. P. Zarubinc, P. P. Puryginc, A. A. Golovanova,*, and S. S. Zlotskiid Presented by Academician A.A. Berlin March 16, 2020 Received April 14, 2020; revised June 15, 2020; accepted August 4, 2020
Abstract—Previously unknown N-acyl derivatives of 1,2,3-triazole chalcones have been prepared by the acylation of the potassium salts of 4-(3-oxo-3-phenylprop-1-en-1-yl)-5-phenyl-1,2,3-triazolides with carboxylic acid chlorides. The introduction of the N-acyl residue into the heterocyclic moiety of 1-aryl-3-(1H1,2,3-triazol-4-yl)prop-2-en-1-ones has been shown to afford compounds with antibacterial activity. Keywords: 1,2,3-triazoles, chalcones, N-acyl derivatives, antibacterial activity DOI: 10.1134/S0012500820360021
clic compounds IIIa, IIIb, and IVa–IVc in 89–92% yields. Compounds VIIa, VIIb, and VIII were obtained in similar manner from 1-phenyl-5-arylpent-1-en-4-yn-3-ones Va and Vb, via intermediate potassium salts VIa and VIb (Fig. 1, Table 1). The structure of the isolated products was confirmed by NMR spectra (Table 2). The 1H NMR spectra of chalcones IIIa, IIIb, VIIa, and VIIb show the characteristic signals of trans-vinyl protons in the region δH 7.7–8.1 ppm (3JHH 15–16 Hz) and the broadened singlets of NH groups of the heterocyclic moiety in the region δH 7–16 ppm. The 13C NMR spectra show the carbon resonance of the keto group at δC 188–192 ppm. The other signals correspond to the protons and carbon atoms of aryl rings. The spectra of compounds IVa–IVc and VIII and their precursors IIIa, IIIb, VIIa, and VIIb as a whole are similar and indicates the regioselective acylation of salts IIa, IIb and VIa, VIb. The carbon nuclei of the carbonyl groups in the 13C NMR spectra of N-acyl chalcones IVa–IVc and VIII have chemical shifts δC 164–166 (RC(O)N) and 188–193 ppm (C(O)CH=CH). Biological testing results (Table 3) indicate that non-acylated chalcones IIIa, IIIb and VIIa, VIIb and their N-benzoyl derivative VIII do not suppress Staphylococcus aureus bacteria, whereas the minimal inhibiting concentrations (MIC) of compounds IVa–IVc are at the level of the most active quinoline derivatives of 1,2,3-triazole [6]. The current study has shown for the first time that the antibacterial activity of N-acyl derivatives 1,2,3-triazole chalcones is affected by the position of the keto group in the propenone fragment.
The functional derivatives of 1,2,3-triazole and benzotriazole are efficient agents against Staphylococcus aureus, one of the main human pathogens that causes a wide spectrum of clinical infections [1–3]. For example, 1,2,3-triazoles containing coumarine [1] and quinoline substituents [2, 3], arylhydrazones of 1aryl-1,2,3-triazole-4-carbaldehydes [4], bis-triazole derivatives [5], and triazolecarboxylate esters [6] show distinct antimicrobial effect. At present, the researchers are searching for new antibacterial compounds of triazole series showing low toxici
Data Loading...
