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An efficient synthesis of rearranged new biologically active benzimidazoles derived from 2-formyl carvacrol

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Abstract

A new series of benzimidazole derivatives was synthesized by one-pot two-step reaction as a result of unexpected rearrangement during reaction of 2-formyl carvacrol and corresponding 2-phenylenediamines in DMF, by using Na2S2O5 as an oxidizing reagent. The newly synthesized compounds were characterized by 1H NMR, 13C NMR, FT-IR, mass spectroscopy techniques, and single-crystal X-ray crystallography. The docking studies of all nine compounds were carried out against the active site of the Plasmodium falciparum dihydroorotate dehydrogenase enzyme. To inspect their antimalarial, antimicrobial, and antioxidant activity, all the synthesized compounds were screened in vitro for their antimalarial activity against the malaria parasite Plasmodium falciparum strain and four bacterial as well as three fungal strains. The biological screening revealed that some synthesized compounds have very good antimalarial activity. The physicochemical properties were calculated for all the synthesized benzimidazoles and were found to be good oral bioavailability drugs as resolute by Lipinski's rule.

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Acknowledgements

The authors are grateful to the UGC, New Delhi, SAP (DSA-I) Ref. No. F. 4-6/2015/DSA-I (SAP-II) for providing financial assistance.

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Authors and Affiliations

  1. School of Chemical Sciences, Kavayitri Bahinabai Chaudhari, North Maharashtra University, Jalgaon, Maharashtra, 425001, India

    Rahul T. Bhoi & Ratnamala S. Bendre

  2. Department of Chemistry, Faculty of BP Arts, SMA Science and KKC Commerce College, Chalisgaon, Maharashtra, 424101, India

    Jamatsing D. Rajput

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  1. Rahul T. Bhoi
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  2. Jamatsing D. Rajput
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  3. Ratnamala S. Bendre
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Correspondence to Ratnamala S. Bendre.

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Bhoi, R.T., Rajput, J.D. & Bendre, R.S. An efficient synthesis of rearranged new biologically active benzimidazoles derived from 2-formyl carvacrol. Res Chem Intermed 48, 401–422 (2022). https://doi.org/10.1007/s11164-021-04601-9

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  • DOI: https://doi.org/10.1007/s11164-021-04601-9

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