Design, synthesis and antibacterial activity of substituted 1- [(2-aryl-1,3-dioxolan-4-yl)methyl]-1H-azoles

• Published in: Journal of pharmaceutical sciences and research Vol. 10; no. 2; pp. 328 - 332
• Main Authors: Talismanov, V S, Popkov, S V, Zykova, S S, Karmanova, O G
• Format: Journal Article
• Language: English
• Published: Cuddalore Journal of Pharmaceutical Sciences and Research 01.02.2018
• Subjects: Antimicrobial agents; Chemistry; Drugs; Enzymes; Gram-positive bacteria; Pharmaceutical sciences
• ISSN: 0975-1459

The resulting crystals of product's oxalates were filtered off, washed with 10 ml acetone and 40 ml hexane and dried in air. 1-{[2-(4-chlorophenyl)-2-propyl-1,3-dioxolan-4 yl]methyl}-iff-1,2,4-triazole (1b), yield 68%, m.p. 62-63 °C. NMR'H (DMSO-d6, 5, ppm, J/Hz): 0.68 (t, 3H, CH2CH3, 3J = 7.3 ); 1.06 (sext, 2H, CH2CH3, 3J = 7.8, 2J = 16.1); 1.56-1.71 (m, 2H, CH2CH2CH3); 3.44 (d.d, 0.45H, CH2O, 3J = 7.9, 2J = 8.6); 3.60 (d.d, 0.55H, CH2O, 3J = 7.9, 2J = 8.6); 3.80 (d.d, 0.55H, CH2O, 3J = 5.8, 2J = 8.6); 3.94-4.49 (m, 3.45H, CH2O +CH2N + CHO); 7.18-7.36 (m, 4H, Ar); 7.83 (s, 0.45H, C3H triaz.); 7.90 (s, 0.55H, C3H triaz.); 8.31 (s, 0.45H, C5H triaz.). Results and discussion In previous paper we have shown high fungicidal activity of 1-[(2-aryl-1,3-dioxolan-4-yl) methyl]-1H-azoles with logP in the range 3.0-4.0, having bulky lipophilic substituent at the para-position of the aryl cycle [15]. [...]the design of the target compounds consisted of the modification of the structure by various bulky and lipophilic substituents in the paraposition (chloro-, cyclohexyl-, ŕerŕbutyl-), and preliminary calculation of logP by experimental and calculation methods [61]. The antimicrobial activity of the synthesized compounds was studied at Hans-Knoell-Institute for Natural Products Research (Germany) against Gram-positive bacteria: Based on the results of biological tests, it was shown that all synthesized compounds possess antimicrobial activity, and 1-{[2,2-bis(4chlorophenyl)-1,3-dioxolan-4-yl]methyl}-?-imidazole exceeds ciprofloxacin in activity against Staphylococcus aurelius that confirms the prospect of searching for new antibacterial substances in the series of substituted 1-[(2-aryl-1,3-dioxolan-4yl)methyl]-1H-azoles.