(Z)-3-Amino-5-(pyridin-2-ylmethylidene)-2-thioxo-1,3-thiazolidin-4-one

Hirsova, Petra; Dolezel, Jan; Kučerová-Chlupáčová, Marta; Kuneš, Jiřı́; Pilařová, Veronika; Nováková, Lucie; Opletalová, Veronika

doi:10.3390/m872

Cited by 6 publications

(3 citation statements)

References 22 publications

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“…27 Compounds 2a1-2, 2b1-2 were synthesized via Knoevenagel condensation between aldehyde and the final stages of the first step (1a, 1b), which are N-substituted rhodanine, using NH 4 OH/NH 4 Cl as a catalyst and reflux for 6-8 hrs. Condensation in alcoholic solution in an environment of NH 4 OH/NH 4 Cl always resulted in 5-[(aryl) alkylidene]-3aminorhodanine 50 ; Petlichnaya and colleagues obtained similar results (1967 and 1970). 48,49 In the synthesis procedure, compounds were highly affected by increasing heat, so the used reflux temperature was not more than 50°C-60°C.…”

Section: Resultsmentioning

confidence: 81%

New 3-aminorhodanine derivatives: Synthesis, characterization, docking study and biological activates

Khalaf,

Hasan,

Ali

2023

F1000Res

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Background: Epidermal growth factor receptor (EGFR) is seen in almost all cases of non-small cell lung cancer (NSCLC). As a result, targeting EGFR has become an attractive subject of research in fields such as antitumor research and the most important strategy for cancer treatment, in particular, in the treatment of non-small-cell lung malignancies using EGFR-targeting therapies. Methods: For this purpose, novel N- and 5- disubstituted aminorhodanine derivatives were synthesized by Schiff base and using a Knoevenagel condensation approach over two steps of reactions. Then, rhodanine derivatives were analyzed their cytotoxic effect on A549 lung cancer and Hdfn normal cell and compared the analysis result with erlotinib (anticancer drug) as standard to determine their activities on cancer cell and toxicity or safety on normal cell. Results: Synthetic compounds (2a1-2, 2b1-2) showed different effects at 24, 48 and 72h. The higher anticancer effect was seen for 2a2 and 2a1with IC50 10 μg/mL and 32.59 μg/mL, respectively, at 24h and 72 h. Also, they show high anticancer potency at 72h with low effect and high safety on human normal cell. Conclusions: Developing a new series of rhodanine derivatives and evaluating their anticancer activity is the main goal of the study. In silico and in vitro antitumor investigations for newly synthesized compounds with different properties and functional group in chemical structure revealed different activities against lung cancer cell. Compounds 2a1-2 which contain pyridine ring in their chemical structure showed more potent effect than the derivative that bearing furyl ring (2b1-2).

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Section: Resultsmentioning

confidence: 81%

New 3-aminorhodanine derivatives: Synthesis, characterization, docking study and biological activates

Khalaf,

Hasan,

Ali

2023

F1000Res

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“…Encouraged by the success of the above reaction, we became interested in the mechanism. Several condensation examples of Naminorhodanine with aldehyde or ketone derivatives have been reported in literature [24] Depending on the reaction conditions, Naminorhodanine can react with aldehyde or ketone derivatives either at the C-5 position through a condensation reaction to form the 5-(aryl)alkylidene compound [25,26] or with primary amine group to conduct to the Schiff base derivative. The former reaction, known as Girard's method is usually favored in ammoniacal medium while heating in alcohols or in the presence of acid catalysis as glacial acetic acid or hydrochloric acid gives usually the Schiff base compounds as illustrated in Scheme 4.…”

Section: Chemistrymentioning

confidence: 99%

Synthesis and evaluation of new isatin-aminorhodanine hybrids as PIM1 and CLK1 kinase inhibitors

Khaldoun

Safer

Boukabcha

et al. 2019

Journal of Molecular Structure

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“…Research on the potential of certain heterocyclic small molecules as effective anticancer drugs has been conducted extensively in recent years. Rhodanine-based derivatives − exhibited remarkable biological properties as anticonvulsant, antibacterial, antiviral, Hepatitis C Virus (HCV), and antidiabetic medicines, making them a privileged scaffold in the field of drug development. − As potential tumor aggregation inhibitors, radonine and other 2-thioxo-4-thiazolidinone alternatives have recently been investigated. − Rhodanine and its bioisostere 2,4-thiazolidinedione (TZD) are examples of heterocyclic substances with a thiazolidine nucleus. , Figure shows that rhodanine derivatives can be promising scaffold with Topo-II inhibition activity . One of these mimics (ERK) is Raf/MEK/extracellular signal-regulated kinase, and pathways for Wnt signal transduction have been connected to carcinogenesis, tumor development, and metastasis .…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, Computational Investigations, and Antitumor Evaluation ofN-Rhodanine Glycosides Derivatives as Potent DNA Intercalation and Topo II Inhibition against Cancer Cells

et al. 2023

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Nitrogen and sulfur glycosylation was carried out via the reaction of rhodanine (1) with α-acetobromoglucose 3 under basic conditions. Deacetylation of the protected nitrogen nucleoside 4 was performed with CH 3 ONa in CH 3 OH without cleavage of the rhodanine ring to afford the deprotected nitrogen nucleoside 6. Further, deacetylation of the protected sulfur nucleoside 5 was performed with CH 3 ONa in CH 3 OH with the cleavage of the rhodanine ring to give the hydrolysis product 7. The protected nitrogen nucleosides 11a−f were produced by condensing the protected nitrogen nucleoside 4 with the aromatic aldehydes 10a−f in C 2 H 5 OH while using morpholine as a secondary amine catalyst. Deacetylation of the protected nitrogen nucleosides 11a−f was performed with NaOCH 3 /CH 3 OH without cleavage of the rhodanine ring to afford the deprotected nitrogen nucleosides 12a−f. NMR spectroscopy was used to designate the anomers' configurations. To examine the electrical and geometric properties derived from the stable structure of the examined compounds, molecular modeling and DFT calculations using the B3LYP/6-31+G (d,p) level were carried out. The quantum chemical descriptors and experimental findings showed a strong connection. The IC 50 values for most compounds were very encouraging when evaluated against MCF-7, HepG2, and A549 cancer cells. Interestingly, IC 50 values for 11a, 12b, and 12f were much lower than those for

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(Z)-3-Amino-5-(pyridin-2-ylmethylidene)-2-thioxo-1,3-thiazolidin-4-one

Cited by 6 publications

References 22 publications

New 3-aminorhodanine derivatives: Synthesis, characterization, docking study and biological activates

New 3-aminorhodanine derivatives: Synthesis, characterization, docking study and biological activates

Synthesis and evaluation of new isatin-aminorhodanine hybrids as PIM1 and CLK1 kinase inhibitors

Design, Synthesis, Computational Investigations, and Antitumor Evaluation ofN-Rhodanine Glycosides Derivatives as Potent DNA Intercalation and Topo II Inhibition against Cancer Cells

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