ArticleMolecules (Basel, Switzerland)2013
Synthesis, antifungal and antitumor activity of novel (Z)-5-hetarylmethylidene-1,3-thiazol-4-ones and (z)-5-ethylidene-1,3-thiazol-4-ones.
Article in Molecules (Basel, Switzerland), 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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7 citing papers in PubMed, 27 citations in OpenAlex.
- Anticancer Profile of Rhodanines: Structure-Activity Relationship (SAR) and Molecular Targets-A Review.Molecules (Basel, Switzerland) · 2022Review
- Challenging inflammatory process at molecular, cellular and in vivo levels via some new pyrazolyl thiazolones.Journal of enzyme inhibition and medicinal chemistry · 2021Article
- Design, synthesis and mechanistic study of new benzenesulfonamide derivatives as anticancer and antimicrobial agentsRSC advances · 2021Article
- Antioxidant activity and antibacterial evaluation of new thiazolin-4-one derivatives as potential tryptophanyl-tRNA synthetase inhibitors.Journal of enzyme inhibition and medicinal chemistry · 2019Article
- Synthesis, Antitumor Evaluation and Molecular Docking of New Morpholine Based Heterocycles.Molecules (Basel, Switzerland) · 2017Article
- Design, Synthesis and Antifungal Activity Evaluation of New Thiazolin-4-ones as Potential Lanosterol 14α-Demethylase Inhibitors.International journal of molecular sciences · 2017Article
- Synthetic approaches, structure activity relationship and biological applications for pharmacologically attractive pyrazole/pyrazoline-thiazolidine-based hybrids.European journal of medicinal chemistry · 2016Review
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Authors and funding
11 authors at 3 institutions in 3 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
New hetaryl- and alkylidenerhodanine derivatives 3a-d, 3e, and 4a-d were prepared from heterocyclic aldehydes 1a-d or acetaldehyde 1e. The treatment of several rhodanine derivatives 3a-d and 3e with piperidine or morpholine in THF under reflux, afforded (Z)-5-(hetarylmethylidene)-2-(piperidin-1-yl)thiazol-4(5H)-ones and 2-morpholinothiazol-4(5H)-ones 5a-d, 6a-d, and (Z)-5-ethylidene-2-morpholinothiazol-4(5H)-one (5e), respectively, in good yields. Structures of all compounds were determined by IR, 1D and 2D NMR and mass spectrometry. Several of these compounds were screened by the U.S. National Cancer Institute (NCI) to assess their antitumor activity against 60 different human tumor cell lines. Compound 3c showed high activity against HOP-92 (Non-Small Cell Lung Cancer), which was the most sensitive cell line, with GI₅₀ = 0.62 μM and LC₅₀ > 100 μM from the in vitro assays. In vitro antifungal activity of these compounds was also determined against 10 fungal strains. Compound 3e showed activity against all fungal strains tested, but showed high activity against Saccharomyces cerevisiae (MIC 3.9 μg/mL).
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