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A convenient one-pot synthesis of novel heterocyclic systems of 9-chloro-4-methyl-6,11-dihydro-5H-benzo[b]pyrimido[4,5-e][1,4]diazepine and inhibitory evaluation against bromodomain-containing protein 4 (BRD4) enzyme by molecular docking

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Abstract

A convenient one-pot two-step strategy for synthesis of the novel tricyclic system 9-chloro-4-methyl-6,11-dihydro-5H-benzo[b]pyrimido[4,5-e][1,4]diazepine have been synthesized through the heterocyclization reaction of 2,4-dichloro-5-(chloromethyl)-6-methylpyrimidine with 4-chloro-o-phenylenediamine under basic conditions. Various derivatives were obtained via treatment with secondary amines. Also, the inhibitory effects of the synthesized compound against bromodomain-containing protein 4 (BRD4) have been evaluated by molecular docking. The results reveal that among the studied compounds (5f) is a more potent inhibitor against this enzyme.

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Acknowledgements

We gratefully appreciate Ferdowsi university of the Mashhad Research council for their financial support of this work (grant: 3/53924).

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Ferdowsi University of Mashhad, Mashhad, 91775-1436, Iran

    Fahimeh Assadzadeh, Toktam Afrough, Hossein Eshghi & Hossein Sabet-Sarvestani

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  1. Fahimeh Assadzadeh
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  2. Toktam Afrough
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  3. Hossein Eshghi
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  4. Hossein Sabet-Sarvestani
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Correspondence to Hossein Eshghi.

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Assadzadeh, F., Afrough, T., Eshghi, H. et al. A convenient one-pot synthesis of novel heterocyclic systems of 9-chloro-4-methyl-6,11-dihydro-5H-benzo[b]pyrimido[4,5-e][1,4]diazepine and inhibitory evaluation against bromodomain-containing protein 4 (BRD4) enzyme by molecular docking. J IRAN CHEM SOC 20, 2841–2848 (2023). https://doi.org/10.1007/s13738-023-02880-0

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