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Kaolin-catalysed one-pot synthesis of thiophene containing aminonaphthols under solvent-free condition and their in vitro anticancer and antioxidant activity

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Abstract

An efficient and eco-friendly synthetic protocol via a one-pot three-component reaction to yield thiophene containing aminonaphthols (Betti bases) is reported. Kaolin was used as a heterogeneous catalyst and a series of Betti bases were synthesized under solvent-free condition. The synthesized derivatives were characterized by various techniques, viz. FTIR, 1H-NMR, 13C-NMR, mass spectrometry and elemental analysis. The synthesized compounds were screened for in vitro anticancer and antioxidant activities. Compounds 4d, 4i, 4j exhibited excellent anticancer activity (GI50 < 10 µg/ml) against all four cell lines which was comparable with the standard drug doxorubicin. Compound 4d was found to be the most potent antioxidant against DPPH radical and H2O2. The reusability studies demonstrated the retention in catalytic activity for up to six cycles. The current synthetic methodology offers several advantages such as excellent yields, mild reaction conditions, short reaction span, ease of work-up, broad substrate scope and reusability.

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Acknowledgements

We are thankful to Microanalytical Laboratory, University of Mumbai for providing characterization facilities. We are also thankful to the Tata Memorial Centre’s Advanced Centre for Treatment Research and Education in Cancer (ACTREC) AntiCancer Drug Screening Facility (ACDSF), Kharghar, Navi Mumbai, for providing anticancer activity.

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Authors and Affiliations

  1. Department of Chemistry, University of Mumbai, Santacruz (E), Mumbai, 400 098, India

    Ishita Yellapurkar, Sarfaraz Shaikh, Ganesh Pavale, Sonal Bhabal & M. M. V. Ramana

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  1. Ishita Yellapurkar
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  2. Sarfaraz Shaikh
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  3. Ganesh Pavale
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  4. Sonal Bhabal
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  5. M. M. V. Ramana
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Correspondence to M. M. V. Ramana.

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Yellapurkar, I., Shaikh, S., Pavale, G. et al. Kaolin-catalysed one-pot synthesis of thiophene containing aminonaphthols under solvent-free condition and their in vitro anticancer and antioxidant activity. Res Chem Intermed 47, 4067–4082 (2021). https://doi.org/10.1007/s11164-021-04516-5

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