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Journal of Sciences, Islamic Republic of Iran
Abstract
Substituted Schiff bases (hydrazones) 5a-j have been prepared from the starting material 2-chloro pyridine-3-carboxylic acid 1 by a sequence of reactions like reaction with 2-amino-6-nitro benzothiazole (Ullamann condensation), thionyl chloride, hydrazine hydrate and different aromatic aldehydes. On cyclocondensation of 5a-j with thioglycolic acid in dry 1,4-dioxane furnished desired compounds 4-thiazolidinones 6a-j. The structures of all the synthesized compounds have been assigned on the basis of IR,
1
H NMR,
13
C NMR spectral data and elemental analyses. All the newly synthesized compounds were tested for their in vitro antimicrobial activity against several microbes. Some of the compounds showed significant antibacterial as well as antifungal activity.
The synthesis of 4-thiazolidinones of 2-amino-5-chloropyridine was performed by novel method of stirring involving the cyclocondensation of the appropriate Schiffs bases (2a–c) with thioglycolic acid, followed by the addition of zinc chloride in the presence of molecular sieves. Characterization of the synthesized compounds, determination of purity and identity of the compounds using following spectroscopic and chromatographic techniques- Solubility,Thin Layer Chromatographic studies, Ultra-Violet studies,Rotational and vibrational studies (FT-IR), 1H-NMR studies. The compounds were investigated for their Anticonvulsant activity by isoniazid induced convulsions in mice model.Compound3-(5-chloropyridin-2-yl)-2-(4-fluorophenyl) thiazolidin-4-one(3c)was found to be the most activeand compound 3-(5-chloropyridin-2-yl)-2-(2-hydroxyphenyl) thiazolidin-4-one (3a) was found to be less active among the tested compound according to pharmacological evaluation exhibited anticonvulsant activity.
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