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DBU-Catalyzed Efficient One-Pot Three-Component Synthesis of Aminoquinoline Derivatives via Betti Reaction in Polar Medium and Antidiabetic Activity of the Products

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Abstract

Aminoquinoline derivatives are known for their superlative efficacy in the treatment of many diseases. An efficient synthesis of Betti bases via a one-pot three-component reaction of 2-bromophenol, substituted aldehydes, and 3-aminoquinoline in polar media using DBU as a catalyst is reported considering its atom economy, short reaction time, good yield, and easy workup. The obtained compounds were well characterized by IR, NMR, and mass spectra and were screened in vitro for their antidiabetic activity against acarbose as reference drug. Compounds having chloro substituents were found to exhibit significant activity while those with NO2, Br, and F substituents showed moderate activity. The lowest antidiabetic properties were found in the compounds with electron-donating groups (Me).

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ACKNOWLEDGMENTS

The authors are thankful to Saurashtra University and RK University for providing laboratory and library facilities for carrying out this work. R. Makwana is thankful to NFDD, CoE, Department of Chemistry for spectral analysis, and K. Kapadiya is thankful to the Department of Micro­biology for biological study in a very short time.

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Authors and Affiliations

  1. Department of Chemistry, M. M. Science College, Affiliated to Saurashtra University, 363642, Morbi, Gujarat, India

    R. R. Makwana & J. M. Parmar

  2. Department of Chemistry, School of Science, RK University, 360020, Rajkot, Gujarat, India

    K. M. Kapadiya

Authors
  1. R. R. Makwana
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  2. K. M. Kapadiya
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  3. J. M. Parmar
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Correspondence to J. M. Parmar.

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Makwana, R.R., Kapadiya, K.M. & Parmar, J.M. DBU-Catalyzed Efficient One-Pot Three-Component Synthesis of Aminoquinoline Derivatives via Betti Reaction in Polar Medium and Antidiabetic Activity of the Products. Russ J Org Chem 59, 689–694 (2023). https://doi.org/10.1134/S1070428023040188

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