Abstract
Here we describe the synthesis and the antifibrotic and anticancer activity determination of amino(imino)thiazolidinone derivatives. An efficient one-pot three-component reaction which involved [2 + 3]-cyclocondensation and Knoevenagel condensation was used for the synthesis of 5-ene-2-amino(imino)-4-thiazolidinones. Following amino-imino tautomerism, the compound structures were confirmed by X-ray analysis. Comparison of SRB assays on fibroblasts and cancer cells revealed that compounds which significantly reduced the viability of fibroblasts did not possess an anticancer effect. A series of thiazolidinone derivatives as interesting candidates for further testing has been identified. Among the tested compounds 2-{3-furan-2-ylmethyl-2-[(2-methyl-3-phenylallylidene)hydrazono]-thiazolidin-4-one-5-yl}-N-(3-trifluoromethylphenyl)-acetamide (5), N-(2-methoxyphenyl)-2-[5-(4-oxothiazolidin-2-ylideneamino)-[1,3,4]thiadiazol-2-ylsulfanyl]-acetamide (12), 3-[3-allyl-4-oxo-2-(thiazol-2-ylimino)thiazolidin-5-ylidene]-1,3-dihydroindol-2-one (33), and 5(Z)-(thiophen-2-ylmethylene)-4-(4-chlorophenylamino)thiazol-2-(5H)-one (34) possessed high antifibrotic activity levels, had a similar effect as Pirfenidone, and did not scavenge superoxide radicals. Their antifibrotic potential was confirmed using the xCelligence system.
Original language | English |
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Pages (from-to) | 180-195 |
Number of pages | 16 |
Journal | European Journal of Medicinal Chemistry |
Volume | 112 |
DOIs | |
Publication status | Published - 13 Apr 2016 |
Keywords
- Amino/amino-thiazolidinones
- Synthesis
- One-pot method
- Antifibrotic activity
- Superoxide radicals
- Antiproliferative effects
- IDIOPATHIC PULMONARY-FIBROSIS
- CANCER CELL-LINES
- MEDICINAL CHEMISTRY
- ANTIINFLAMMATORY AGENTS
- ANTITUMOR-ACTIVITY
- CRYSTAL-STRUCTURES
- DRUG DISCOVERY
- DERIVATIVES
- 4-THIAZOLIDINONES
- ANTIOXIDANTS