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Novel tetrahydropyrimidine–adamantane hybrids as anti-inflammatory agents: synthesis, structure and biological evaluation

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Abstract

A series of novel (3-((3s,5s,7s)-adamantan-1-yl)-1-alkyl/aralkyl/aryl-1,2,3,4-tetrahydroyrimidin-5-yl)(aryl)methanones (5a–j) has been synthesized by the reaction of 1-aryl-3-(alkyl/aralkyl/aryl)aminoprop-2-en-1-ones 3a–j, 1-adamantanamine 4 and formaldehyde under thermal conditions. The structures of the products (5a–j) have been established with the help of spectral and analytical data. The stereochemistry of the products was established by X-ray crystallographic studies of a representative product (3-((3s,5s,7s)-adamantan-1-yl)-1-methyl-1,2,3,4-tetrahydropyrimidin-5-yl)(4-chlorophenyl) methanone (5g) of the series. The target adamantane–tetrahydropyrimidine hybrids 5a–j were evaluated for their anti-inflammatory activities as a result of which compounds 5e (R=C6H5CH2, Ar=C6H5), 5i (R=CH3, Ar=4-CH3C6H4), 5j (R=C6H5CH2, Ar=4-CH3C6H4) and 5g (R=CH3, Ar=4-ClC6H4 ) were found to exhibit excellent and promising anti-inflammatory activities.

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Acknowledgments

Authors wish to thank Rev. Fr. Dr. Stephen Mavely, Vice Chancellor, Assam Don Bosco University, for providing infrastructure for the execution of this work. 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. Our thanks are also due to the Department of Biotechnology (DBT), Government of India, for a research grant. UK, SK & RN thank DBT-GOI for research fellowships.

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Authors and Affiliations

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

    Utpalparna Kalita, Shunan Kaping & Jai Narain Vishwakarma

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

    Revinus Nongkynrih & 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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  4. Laishram Indira Singha
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  5. Jai Narain Vishwakarma
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Correspondence to Jai Narain Vishwakarma.

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Kalita, U., Kaping, S., Nongkynrih, R. et al. Novel tetrahydropyrimidine–adamantane hybrids as anti-inflammatory agents: synthesis, structure and biological evaluation. Med Chem Res 24, 2742–2755 (2015). https://doi.org/10.1007/s00044-015-1332-x

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  • DOI: https://doi.org/10.1007/s00044-015-1332-x

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