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Microwave-Assisted Triflic Anhydride Mediated Mild and Efficient Method for the Synthesis of Novel Enamine Functionalized Benzothiophene Derivatives and Their Anticancer Activity

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Abstract

A series of triflic anhydride mediated novel enamine functionalized benzothiophene derivatives were designed, synthesized by microwave-assisted triflic anhydride mediated protocol and analyzed by various spectroscopic methods. The synthesized benzothiophene derivatives were screened for their anticancer activity against MCF-7 breast cancer cells and human leukemia cell line K-562. The compounds exhibited activity ranging from weak to significant in terms of percentage cytotoxicity. Amongst the screened compounds, compound N,N-dibutyl-6-ethylbenzo[b]thiophen-3-amine (IVc) possess potential anticancer activity. Furthermore, SAR studies indicated that presence of n-butyl group will increase the anticancer activity, on the other hand compound N,N-dibutyl-6-chlorobenzo[b]thiophen-3-amine (IIc) is inactive, and from this result it is indicating that presence of electron withdrawing group does not have possible anticancer activity. We have an opinion that, this developed model helps us in future to develop more potential enamine functionalized benzothiophene derivatives for their anticancer activity.

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ACKNOWLEDGMENTS

The authors sincerely thank Anti-Cancer Drug screening facility (ACDSF) at ACTREC, Tata Memorial Centre, Navi Mumbai for in vitro testing for anticancer activity evaluation.

Funding

This work was made possible by a grant from the Department of Science and Technology (DST), New Delhi (grant no. SB/EMEQ-323/2014).

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Authors and Affiliations

  1. Department of Chemistry, Koneru Lakshmaiah Education Foundation, 522302, Vaddeswaram, India

    Pommidi Anil, Srinivas Endoori & Venkateswara Rao Anna

  2. Department of Chemistry, Palamuru University, Mahabubnagar, 509001, Telangana, India

    Munugala Chandrakanth & Somarapu Vijaya Laxmi

  3. Department of S&H, PSCMR College of Engineering and Technology, 520001, Vijayawada, India

    Thirumala Prasad Kota

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  1. Pommidi Anil
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  4. Thirumala Prasad Kota
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  5. Venkateswara Rao Anna
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  6. Somarapu Vijaya Laxmi
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Contributions

Author PA designed the experiments and synthesized samples. Authors SE, MC synthesized samples, participated in data processing. Author TPK participated in data processing. Author VRA contributed to manuscript preparation. Author SVL designed the experiments and contributed to manuscript preparation. All authors participated in the discussion.

Corresponding author

Correspondence to Somarapu Vijaya Laxmi.

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This article does not contain any studies involving animals or human participants performed by any of the authors.

Informed consent was not required for this article. No conflict of interest was declared by the authors.

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Anil, P., Endoori, S., Chandrakanth, M. et al. Microwave-Assisted Triflic Anhydride Mediated Mild and Efficient Method for the Synthesis of Novel Enamine Functionalized Benzothiophene Derivatives and Their Anticancer Activity. Russ J Bioorg Chem 49, 1034–1042 (2023). https://doi.org/10.1134/S1068162023050102

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