Journal
RUSSIAN JOURNAL OF BIOORGANIC CHEMISTRY
Volume 38, Issue 5, Pages 539-549Publisher
MAIK NAUKA/INTERPERIODICA/SPRINGER
DOI: 10.1134/S106816201205010X
Keywords
piperazin; 1,3-thiazolidinone; 1,2,4-triazole; 1,3,4-thiadiazole; antimicrobial activity
Funding
- Karadeniz Technical University, BAP, Turkey [2007.111.002.6]
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3-Fluoro-4-(4-phenylpiperazin-l-yl)aniline (II) prepared from 3,4-difluoro nitrobenzene was converted to the corresponding Schiff bases (III) and (IV) by treatment with 4-methoxybenzaldehyde and indol-3-carbaldehyde, respectively. Treatment of amine (II) with 4-fluorophenyl isothiocyanate afforded the corresponding thiourea derivative (V). Compound (V) was converted to thiazolidinone and thiazoline derivatives (VI) and (VII) by cyclocondensation with ethylbromoacetate or 4-chlorophenacylbromide, respectively. The synthesis of carbothioamide derivative (X) was performed starting from compound (II) by three steps. Treatment of compound (X) with sodium hydroxide, sulfuric acid, or chlorophenacyl bromide generated the corresponding 1,2,4-triazole (XI), 1,3,4-thiadiazole (XII), and 1,3-thiazolidinone (XIII) derivatives, respectively. The structural assignments of new compounds were based on their elemental analysis and spectral (IR, H-1-NMR, C-13-NMR, and LC-MS) data. In the antimicrobial activity study all the compounds revealed high anti-Mycobacterium smegmatis activity.
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