Two Novel Triazolo-Thiadiazepines: Synthesis, Stereostructure, Antimicrobial and Cytotoxic Activity
DOI:
https://doi.org/10.12970/2308-8044.2014.02.02.2Keywords:
Substituted triazole, α,β-unsaturated enones, uncyclized adducts, triazolo-thiadiazepines, antimicrobial activity, cytotoxic activity.Abstract
Two novel triazolo-thiadiazepines, 2-(4-chlorophenyl)-4-[2-(4-chlorophenyl)ethenyl]—7-(9-decenyl)-2,3-dihydro-1,2,4- triazolo [3,4-b] [1,3,4] thiadiazepine (4) and 2,4-bis (4-chlorophenyl)-7-(9-decenyl)-2,3-dihydro-1,2,4-triazolo[3,4-b] [1,3,4]thiadiazepine (7) are synthesized from 3-(9-decenyl)-4-amino-5-mercapto-1,2,4-triazole (1) using 1,5-bis(4-chlorophenyl)pent-1,4-dien-3-one (2) in the former and 4,4’-dichlorochalcone (5) in the latter. The uncyclized adducts, 1,5-bis(4-chlorophenyl)-5-[3-(9-decenyl)-4-amino-5-thio-1,2,4-triazolyl]pent-1-en-3-one (3) and 1,3-bis(4-chlorophenyl)-3-[3-(9-decenyl)-4-amino-5-thio-1,2,4-triazolyl]propan-1-one (6) are also respectively obtained with them. The reaction of (1) with 1,3-bis(2-thienyl)propen-1-one (8) yielded only the uncyclized adduct, 1,3-bis(2-thienyl)-3-[3-(9-decenyl)-4-amino-5-thio-1,2,4-triazolyl]propan-1-one (9) as the sole product. The triazole (1) is prepared from commercially available 10-undecenoic acid by reaction with thiocarbohydrazide at 170oC. The α, β -unsaturated enones, 1,4-dien-3-one (2), dichlorochalcone (5), and thienyl propenone (8) are respectively obtained by condensing acetone with p-chlorobenzaldehyde(molar ratio,1:2), p-chloroacetophenone with p-chlorobenzaldehyde and 2-acetylthiophene with thiophene-2-aldehyde(molar ratios, 1:1) in the presence of 2.5 equivalents of sodium hydroxide.The synthesized compounds (1), (4), (7), and (9) are screened for in vitro antimicrobial and cytotoxic activities. These compounds showed potent antibacterial activity against “Gram negative” bacteria (Escherichia coli and Pseudomonas aeruginosa) but no activity could be demonstrated against Gram positive bacterial strains.Streostuctures are established using IR, DCI-MS, 1H- and 13C- NMR spectra.
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