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Exploration of 2-(Substituted Phenyl)-thiazolidin-4-one as Anticancer Agents

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Abstract

A facile synthesis of (2-(substituted phenyl)-thiazolidin-4-one by using recyclable catalyst β-cyclodextrinSO3H has been achieved. It has been synthesized by successive three-component reaction of substituted benzaldehyde, 6/7-aminoflavone, thioglycolic acid with recyclable catalyst β-cyclodextrin-SO3H. Our research team has performed in vitro anticancer study of all synthesized compounds. Among these synthesized compounds, (IVf) and (IVn) have demonstrated significant in vitro anticancer activity. The compound (IVn) was found to be very potent to standard drug Adriamycin. Additionally, the mechanism of anticancer activity was established by examining the inhibitory activity of synthesized compounds against Human Topoisomerase II (Topo-II). The compounds (IVf) and (IVn) was found to have a good ability to inhibit Topo-II enzyme, which makes them good anticancer agents. The mechanism of anticancer activity was further confirmed by performing docking studies of compounds on Topo-II enzyme.

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Fig. 1.
Scheme 1.
Scheme 2.
Fig. 2.

DATA AVAILABILITY

The data that support the findings of this study are available from the corresponding author upon reasonable request.

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  56. Abbreviations: A-549, Human lung cancer cell lines; Caco-2, Colorectal adenocarcinoma; Cs2CO3, Cesium Carbonate; CTAB, Cetyltrimethyl ammonium bromide; DIPEAc, N,N-diisopropylethylamine; H3BO3, Boric acid; HepG-2, Hepatocellular carcinoma; K2CO3, Potassium carbonate; PEG-400, polyethylene glycol 400; TLC, Thin-layer chromatography; Topo-II, Topoisomerase II; ZnCl2, Zinc chloride; β-CD-SO3H, β-cyclodextrin-SO3H; HepG-2, Hepatocellular carcinoma; A-549, Human lung cancer cell lines; Caco-2, Colorectal adenocarcinoma.

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ACKNOWLEDGMENTS

The authors are thankful to the Principal and Head, Department of Chemistry, Vinayakrao Patil College, Vaijapur, Aurangabad (MS) India, for providing the laboratory facility.

Funding

This work was supported by regular institutional funding, and no additional grants were obtained.

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Authors and Affiliations

  1. Department of Chemistry, Vinayakrao Patil College, Vaijapur, 423701, MS, India

    Rahul B. Shinde & Ashok M. Zine

  2. Department of Chemistry, Deogiri College, Station Road, Aurangabad, 431005, MS, India

    Dattatraya N. Pansare

  3. Department of Chemical Technology, Dr. Babasaheb Ambedkar Marathwada University, Aurangabad, 431004, MS, India

    Aniket P. Sarkate

  4. Department of Pharmaceutical Chemistry, Shri Ramkrishna Paramhans College of Pharmacy, Hasnapur, Parbhani, 431401, MS, India

    Shailee V. Tiwari

  5. Department of Chemistry, R.K.M.M. Ahmednagar, 414001, MS, India

    Rohini N. Shelke

  6. Rajarashi Shahu College of Pharmacy, Buldana, 443001, MS, India

    Deepak Lokwani & Shirish Jain

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  1. Rahul B. Shinde
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Contributions

The authors RBS and DNP—selected the literature data on the review topic. The authors APS, SVT, DL, SJ, and AMZ—contributed to manuscript preparation. All authors participated in the discussions.

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Correspondence to Dattatraya N. Pansare or Ashok M. Zine.

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Abbreviations: A-549, Human lung cancer cell lines; Caco-2, Colorectal adenocarcinoma; Cs2CO3, Cesium Carbonate; CTAB, Cetyltrimethyl ammonium bromide; DIPEAc, N,N-diisopropylethylamine; H3BO3, Boric acid; HepG-2, Hepatocellular carcinoma; K2CO3, Potassium carbonate; PEG-400, polyethylene glycol 400; TLC, Thin-layer chromatography; Topo-II, Topoisomerase II; ZnCl2, Zinc chloride; β-CD-SO3H, β-cyclodextrin-SO3H; HepG-2, Hepatocellular carcinoma; A-549, Human lung cancer cell lines; Caco-2, Colorectal adenocarcinoma.

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Shinde, R.B., Pansare, D.N., Sarkate, A.P. et al. Exploration of 2-(Substituted Phenyl)-thiazolidin-4-one as Anticancer Agents. Russ J Bioorg Chem 49 (Suppl 1), S81–S95 (2023). https://doi.org/10.1134/S1068162023080071

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