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Nitrothiazole-Thiazolidinone Hybrids: Synthesis and in Vitro Antimicrobial Evaluation
Dylan Hart ; Lesetja J. Legoabe ; Omobolanle J. Jesumoroti , et al. Chem. Biodivers.,2022,19(11):e202200729. DOI: 10.1002/cbdv.202200729 PubMed ID: 36102043
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Abstract: Herein we report the synthesis of novel compounds inspired by the antimicrobial activities of nitroazole and thiazolidin-4-one based compounds reported in the literature. Target compounds were investigated in vitro for antitubercular, antibacterial, antifungal, and overt cell toxicity properties. All compounds exhibited potent antitubercular activity. Most compounds exhibited low micromolar activity against S. aureus and C. albicans with no overt cell toxicity against HEK-293 cells nor haemolysis against human red blood cells. Notably, compound 3b exhibited low to sub-micromolar activities against Mtb, MRSA, and C. albicans. 3b showed superior activity (0.25 μg/ml) against MRSA compared to vancomycin (1 μg/ml).
Purchased from AmBeed: 613-45-6 ; 121-66-4 ; 587-04-2 ; 104-87-0 ; 552-89-6 ; 456-48-4 ; 830-79-5 ; 555-16-8 ; 104-88-1 ; 591-31-1 ; 3132-99-8 ; 446-52-6 ; 459-57-4 ; 529-20-4 ; 6287-38-3 ; 123-08-0 ; 100-52-7 ; 349121-09-1 ; 89-98-5 ...More
CAS No. : | 830-79-5 | MDL No. : | MFCD00003313 |
Formula : | C10H12O4 | Boiling Point : | No data available |
Linear Structure Formula : | C6H2(OCH3)3CHO | InChI Key : | CRBZVDLXAIFERF-UHFFFAOYSA-N |
M.W : | 196.20 | Pubchem ID : | 70019 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | |
Hazard Statements: | H315-H319-H335 | Packing Group: | |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium hydroxide; In water; at 60℃; for 12h; | General procedure: To a solution of N-methyl-3-acetylindol (1 mmol) and the benzaldehyde derivative (1 mmol) in methanol (10 ml) was added KOH (1 ml from a 50% solution in H2O). The mixture was heated at 60 C for 12 h then evaporated to dryness. The crude was dissolved in ethyl acetate (30 ml) then washed with HCl (1N, 10 ml) and H2O (10 ml), respectively. The organic layer was separated, dried over Na2SO4 and evaporated. The product was purified by chromatography column eluted with hexane:ethyl acetate (8:2) to yield the title compound as a yellow powder. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium hydroxide; In ethanol; at 20℃; | To a clear solution of 3a (1mmol) in EtOH containing 2, 4, 6-trimethoxy benzaldehyde (1mmol), 40% KOH was added and the resulting reaction mixture was stirred for complition of the reaction at r.t. (TLC control). The separated solid was filtered, washed with excess of water, neutralized with dil HCl, dried over anhydrous Na2SO4, recrystallised from ethanol to obtain product 13. The product was pure enough for further reactions. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium ethanolate; In ethanol; at 20℃; | General procedure: Various aldehydes (1.0 equiv) were added to stirred solutions of indolin-2-one, 5-chloroindolin-2-one or <strong>[5654-97-7]7-azaoxindole</strong> (1.0equiv) in absolute ethanol. After stirring at room temperature for 5 min NaOEt/EtOH (0.5 mL) was added and the mixture was then stirred at room temperature overnight. The solvent was then removed under vacuum. The residue was washed with saturated sodium chloride solution and then extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated under vacuum. The solid part was purified by chromatography over silica gel using ethyl acetate/petroleum ether as the eluent to afford desired compounds 1a-1g, 2a, 3a. |
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