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Design, synthesis, structure elucidation, and biological activities of 3-(substituted amino)-1-(pyridin-4-yl)propenones and 5-isonicotinoyl-1,2,3,4-tetrahydropyrimidine–adamantane hybrids

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Abstract

Novel molecular hybrids of 5-isonicotinoyl-1,2,3,4-tetrahydropyrimidine–adamantane have been synthesized in excellent yields by the reaction of enaminones, 1-adamantanamine, and formaldehyde. Enaminones (Z)-3-alkyl/aralkyl/aryl-1-(pyridin-4-yl)prop-2-en-1-ones have been synthesised by the reaction of 4-acetylpyridine with N,N-dimethylformamide dimethyl acetal and its bioassay test showed good anti-inflammatory property, but no zone of growth inhibition against Bacillus subtilis (MTCC Code-121), Staphylococcus aureus (MTCC Code-9886), Escherichia coli (MTCC Code-1302), and Salmonella enterica (MTCC Code-3232) bacterial strains. The structures of the synthesized compounds have been established with the help of spectral and analytical data. X-ray analysis of a representative candidate of the series 5-isonicotinoyl-1,2,3,4-tetrahydropyrimidine–adamantane was done for the final confirmation of the structure.

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Acknowledgements

The authors wish to thank Rev. Fr. Dr. Stephen Mavely, Vice Chancellor, Assam Don Bosco University for providing infrastructure for the execution of this work. The authors also wish to express their gratitude to IIT, Guwahati, Tezpur University, Tezpur, SAIF-NEHU, Shillong and SAIF-CDRI, Lucknow, for providing spectral and analytical data. The authors also wish to thank the Institutional Biotech Hub, St. Anthony’s College, Shillong, for providing the facilities to carry out the biological tests. Our thanks are also due to the Department of Biotechnology (DBT), Government of India, for a research grant. UK, SK and RN thank DBT-GOI for research fellowships.

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Authors and Affiliations

  1. Organic Research Laboratory, Department of Chemical Science, Assam Don Bosco University, Guwahati, Assam, 781017, India

    Utpalparna Kalita, Shunan Kaping & Jai Narain Vishwakarma

  2. Department of Biotechnology, St. Anthony’s College, Shillong, 793001, India

    Revinus Nongkynrih, Ivee Boiss & Laishram Indira Singha

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  1. Utpalparna Kalita
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  2. Shunan Kaping
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  3. Revinus Nongkynrih
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  6. Jai Narain Vishwakarma
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Correspondence to Jai Narain Vishwakarma.

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Kalita, U., Kaping, S., Nongkynrih, R. et al. Design, synthesis, structure elucidation, and biological activities of 3-(substituted amino)-1-(pyridin-4-yl)propenones and 5-isonicotinoyl-1,2,3,4-tetrahydropyrimidine–adamantane hybrids. Monatsh Chem 148, 2155–2171 (2017). https://doi.org/10.1007/s00706-017-2020-y

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