Design, Synthesis and Evaluation of Novel Rhodanine‐containing Sorafenib Analogs as Potential Antitumor Agents

Li, Wei; Zhai, Xin; Zhong, Zheng; Li, Guangyue; Pu, Yongxiao; Gong, Ping

doi:10.1002/ardp.201000326

Cited by 28 publications

(13 citation statements)

References 15 publications

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“…For example, 5-isopropylidene-3-ethylrhodanine and 5benzylidene-3-ethylrhodanine demonstrated cytotoxicity towards leukemic cell line CEM by inducing apoptosis [38,274]. Besides this, the modification of known drugs, for example assorafenib, with 5ene-4-thiazolidinone fragments 120 is reported [275,276] (Scheme 56).…”

Section: Anticancer Agentsmentioning

confidence: 99%

5-Ene-4-thiazolidinones – An efficient tool in medicinal chemistry

Kaminskyy

Kryshchyshyn

Lesyk

2017

European Journal of Medicinal Chemistry

144

133

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The presented review is an attempt to summarize a huge volume of data on 5-ene-4-thiazolidinones being a widely studied class of small molecules used in modern organic and medicinal chemistry. The manuscript covers approaches to the synthesis of 5-ene-4-thiazolidinone derivatives: modification of the C5 position of the basic core; synthesis of the target compounds in the one-pot or multistage reactions or transformation of other related heterocycles. The most prominent pharmacological profiles of 5-ene derivatives of different 4-thiazolidinone subtypes belonging to hit-, lead-compounds, drug-candidates and drugs as well as the most studied targets have been discussed. Currently target compounds (especially 5-en-rhodanines) are assigned as frequent hitters or pan-assay interference compounds (PAINS) within high-throughput screening campaigns. Nevertheless, the crucial impact of the presence/nature of C5 substituent (namely 5-ene) on the pharmacological effects of 5-ene-4-thiazolidinones was confirmed by the numerous listed findings from the original articles. The main directions for active 5-ene-4-thiazolidinones optimization have been shown: i) complication of the fragment in the C5 position; ii) introduction of the substituents in the N3 position (especially fragments with carboxylic group or its derivatives); iii) annealing in complex heterocyclic systems; iv) combination with other pharmacologically attractive fragments within hybrid pharmacophore approach. Moreover, the utilization of 5-ene-4-thiazolidinones in the synthesis of complex compounds with potent pharmacological application is described. The chemical transformations cover mainly the reactions which involve the exocyclic double bond in C5 position of the main core and correspond to the abovementioned direction of the 5-ene-4-thiazolidinone modification.

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Section: Anticancer Agentsmentioning

confidence: 99%

5-Ene-4-thiazolidinones – An efficient tool in medicinal chemistry

Kaminskyy

Kryshchyshyn

Lesyk

2017

European Journal of Medicinal Chemistry

144

133

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“…Li et al [33] have synthesized a series of rhodanine-containing sorafenib derivatives. The in vitro pharmacological activity indicated that some of the target compounds possessed high antitumor activity against cancer cell lines, such as A549, H460, and HT29, compared to the standard drug sorafenib.…”

Section: Anticancer Activitymentioning

confidence: 99%

Recent Advances in the Biological Importance of Rhodanine Derivatives

Patel¹,

Kumari²

2016

Scope of Selective Heterocycles From Organic and Pharmaceutical Perspective

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Heterocyclic compounds are an important part of the synthetic medicinal chemistry. They offer a high degree of structural variety and have proven to be widely useful as therapeutic agents. Heterocyclic compounds play an important role in the biological processes. They are widespread as natural products. Heterocyclic compounds are widely found in nature categorically in plant alkaloids, nucleic acids, anthocyanins, and flavones. They are also present as in chlorophyll and hemoglobin. "dditionally, some proteins, hormones, and vitamins also contain aromatic heterocyclic system. Heterocycles have huge potential as the most promising molecules as lead structures for the design of new drugs. "bout one half of over million compounds recorded so far in chemical abstracts are heterocyclic. The proposed book chapter entitled, Recent Advances in the Biological Importance of Rhodanine Derivatives gives an outline of importance and applications of the various rhodanine derivatives in medicinal chemistry from to .

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“…Rhodanines have been reported to possess antibacterial, antifungal, antiviral, antimalarial, insecticidal, herbicidal, antitumor, anti-inflammatory and cardiotonic activities (6)(7). Besides, rhodanine derivatives are still broadly evaluated for their anticancer activity against different cancer cell lines, often exhibiting selective toxicity against normal cell lines (8)(9)(10).…”

Section: Introductionmentioning

confidence: 99%

Thiazolidinedione or Rhodanine: A Study on Synthesis and Anticancer Activity Comparison of Novel Thiazole Derivatives

et al. 2017

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-Purpose:A new series of thiazolyl-2,4-thiazolidinedione / rhodanine compounds T1-T23 was synthesized and tested for their anticancer activities. Hepatocellular carcinoma cell lines were chosen due to their strong drug resistance to test the new compounds. Methods: All compounds were synthesized via Knoevenagel Condensation reaction and thiazolidinedione ester compounds (T3,T9,T15,T20) were hydrolyzed for obtaining the acidic compounds (T6,T12,T17,T23). All compounds were firstly screened for their anticancer activity against two hepatocellular carcinoma (HCC) cell lines, Huh7 and Plc/Prf/5 (Plc) cell lines by sulforhodamine B assay. Further IC50 values were calculated for three candidates (T4, T15, T21) in five different HCC (Huh7, Plc, Snu449, HepG2, Hep3B) and one breast cancer (Mcf7) cell line. Results: Compounds T4, T15, T21 had very strong anticancer effects even though their 10 µM concentration in Huh7 cell line. According to IC50 values, T21 was the most effective compound with IC50 values in a range from 2 to 16 µM in 6 cancer cell lines. In terms of cytotoxicity T21 mostly affected Huh7 and interestingly it was less effective against Plc. Conclusions: Considering these results it can be suggested that compounds T4, T15 and T21 may lead to the development of more potent anticancer drugs in the future.

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Design, Synthesis and Evaluation of Novel Rhodanine‐containing Sorafenib Analogs as Potential Antitumor Agents

Cited by 28 publications

References 15 publications

5-Ene-4-thiazolidinones – An efficient tool in medicinal chemistry

5-Ene-4-thiazolidinones – An efficient tool in medicinal chemistry

Recent Advances in the Biological Importance of Rhodanine Derivatives

Thiazolidinedione or Rhodanine: A Study on Synthesis and Anticancer Activity Comparison of Novel Thiazole Derivatives

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