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Identification of potential antileishmanial derivatives of 2,3-dihydroquinazolin-4(1H)-one synthesized using AAIL catalyst and molecular docking studies

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Abstract

A series of 2,3-dihydroquinazolin-4-(1H)-one (DHQ) derivatives have been synthesized under solvent-free conditions. The one-pot multicomponent reaction (MCR) of isatoic anhydride, aromatic aldehydes, and substituted aniline using the prolinium methane sulphonate (ProMSA), a Brønsted amino acid ionic liquid (AAIL) used as a highly efficient green catalyst. Spectroscopic techniques like 1H NMR, 13C NMR, FTIR analysis, and melting point value were used to characterize the synthesized compounds. All the DHQ derivatives were tested for antileishmanial activity against extracellular promastigotes of L. donovoni. Among seventeen synthesized derivatives of DHQ, only five derivatives imparted good bioactivity, with a percent reduction in viability of more than 80% at 50 µg/ml concentration and MIC50 values ranging from 10.67 to 14.65 µg/ml. All the active derivatives of DHQ when subjected to molecular docking studies on the Leishmania major pteridine reductase 1 (PTR1) protein ID (6RXC) showed good binding characteristics. According to the docking and bioactivity results, all five derivatives similarly bind with PTR1. The synthesized bioactive compounds were studied insilico for ADME properties (absorption, distribution, metabolism, and excretion) and showed good drug-likeness character. In the case of L. donovoni, the compounds 4j, 4k, 4o, 4p, and 4q could be promising potential therapeutic candidates.

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Fig. 1
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Authors and Affiliations

  1. Department of Chemistry, Savitribai Phule Pune University, Pune, Maharashtra, 411007, India

    Nitin R. Rode, Aafaq A. Tantray & Santosh S. Terdale

  2. Department of Technology, Savitribai Phule Pune University, Pune, Maharashtra, 411007, India

    Amruta V. Shelar

  3. Department of Zoology, Savitribai Phule Pune University, Pune, Maharashtra, 411007, India

    Kalpana Pai

  4. Department of Biotechnology, Savitribai Phule Pune University, Pune, Maharashtra, 411007, India

    Rajendra H. Patil

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  1. Nitin R. Rode
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Contributions

NRR: Manuscript preparation and major research work (including synthesis and molecular docking study). AAT: Help in synthesizing ionic liquids and their characterization. AVS, KP, and RHP: Help in antileishmanial activity study. NRR and SST: Concept, establishing the methodology, data collection, analysis, interpretation of the results, and manuscript preparation. All authors: All authors reviewed the manuscript.

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Correspondence to Santosh S. Terdale.

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The original online version of this article was revised: The Fig. 2 has been corrected.

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Rode, N.R., Tantray, A.A., Shelar, A.V. et al. Identification of potential antileishmanial derivatives of 2,3-dihydroquinazolin-4(1H)-one synthesized using AAIL catalyst and molecular docking studies. Res Chem Intermed 50, 1125–1145 (2024). https://doi.org/10.1007/s11164-023-05197-y

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