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Design, synthesis and characterization of quinoline–pyrimidine linked calix[4]arene scaffolds as anti-malarial agents

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Abstract

In this paper, we report a series of quinoline-pyrimidine linked calix[4]arene derivatives functionalized with 8-amino quinoline, 5-amino quinoline, 8-hydroxy quinoline, 2-amino pyrimidine and 4-amino 3-methyl quinoline. The synthesized compounds were purified and characterized by elemental analysis, FT-IR, 1H NMR and ESI-MS and screened for their anti-malarial activity against plasmodium falciparum strains. Two synthesized compounds with 8-hydroxy quinoline and 2-amino pyrimidine substituents showed good antimalarial activity with IC50 0.073 and 0.043 µg/ml respectively which is comparable with the standard drug chloroquine. The present study provides valuable information for developing calix[4]arene conjugates quinoline-pyrimidine based derivatives as an effective antimalarial agents.

Graphical Abstract

In this paper, we report a series of quinoline-pyrimidine linked calix [4]arenes derivatives functionalised with 8-amino quinoline, 5-amino quinoline, 8-hydroxy quinoline, 2- amino pyrimidine and 4-amino 3-methyl quinoline and screened for antimalarial activity. Two synthesized compounds with 8-hydroxy quinoline and 2-amino pyrimidine substituents showed good antimalarial activity with IC50 0.073 and 0.043 µg/mL respectively, which is comparable with the standard drug chloroquine. The present study provides valuable information for developing calix[4]arene conjugates quinoline-pyrimidine derivatives.

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Acknowledgments

Nikunj N. Valand would like to acknowledge financial assistance from DST-New Delhi as Innovation in Science Pursuit for Inspire Research (INSPIRE) fellowship. The authors also acknowledge Microcare Laboratory, Surat for the antimalarial activity studies.

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Authors and Affiliations

  1. Department of Chemistry, University School of Sciences, Gujarat University, Ahmedabad, Gujarat, 380009, India

    Rahul B. Shah, Nikunj N. Valand & Shobhana K. Menon

  2. Bhavans Shree I. L. Pandya Arts-Science College, Gujarat University, Dakor, 388225, India

    Pinkesh G. Sutariya

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  1. Rahul B. Shah
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  2. Nikunj N. Valand
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  3. Pinkesh G. Sutariya
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  4. Shobhana K. Menon
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Correspondence to Shobhana K. Menon.

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Shah, R.B., Valand, N.N., Sutariya, P.G. et al. Design, synthesis and characterization of quinoline–pyrimidine linked calix[4]arene scaffolds as anti-malarial agents. J Incl Phenom Macrocycl Chem 84, 173–178 (2016). https://doi.org/10.1007/s10847-015-0581-0

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