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Novel Synthesis, Reactions, and Biological Study of New Morpholino-Thieno[2,3-c][2,7]Naphthyridines as Anti-Cancer and Anti-Microbial Agents

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Abstract

The biological uses of 2,7-naphthyridines have sparked great attention in recent years. For this reason, we synthesized a series of novel 2,7-naphthyridines derivatives and explored their spectrum and biological properties in this study. Substituted tetrahydro-1H-thiopyrano [3,4-c] pyridine-4-carbonitrile (III) was prepared by the reaction of 1-methyl piperidin-4-one (I) with CS2, malononitrile, and triethylamine. The condensed thiopyrane (III) be converted to three-mercapto-7-methyl-1-morpholino-5,6,7,8-tetrahydro-2,7-naphthyridine-4-carbonitrile (IV) by reaction with morpholine. Composite (IV) was used as a starter in heterocyclic compound a series, such as the thieno[2,3-c][2,7]naphthyridines moiety (VIa–i). We used 1рamino-7-methyl-5-morpholino-6,7,8,9-tetrahydrothieno[2,3-c][2,7]naphthyrid ine-2-substituted (VIb, VIe, VIi) compounds as a precursor to create original heterocyclic moieties, namely: pyrimidothienonaphthyridino and pyridothieno naphthyridino in compounds (VII, VIII, IX, X, and XIa, b). Elemental analysis and spectral techniques (Fourier Transform Infrared (FT-IR), Nuclear magnetic resonance (1H NMR, 13C NMR, and mass spectrum)) were affirmed to validate chemical constructions for the recent synthesized compounds. A number of compounds for antimicrobial activity were examined against a variety of bacterial and fungal strains. In addition, some of these compounds showed anticancer activity in liver and cells of breast cancer.

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ACKNOWLEDGMENTS

The authors wish to express their gratitude to Dr. Saber H. Saber, assistant lecturer in the Department of Zoology for his efforts to assist us in the biological research. This work supported by Chemistry Department, Faculty of Science, Assiut and New Vally Universities, Egypt. The authors would like to express their gratitude to everyone at the Chemistry Department for their never-ending support for this research.

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Authors and Affiliations

  1. Chemistry Department, Faculty of Science, Assiut University, 71516, Assiut, Egypt

    Adel M. Kamal El-Dean, Ahmed A. Geies & Fatma K. Abdel-Wadood

  2. Chemistry Department, Faculty of Science, New Valley University, El-Kharja, New Valley, 72511, Egypt

    Reda Hassanien & Eman E. Abd El-Naeem

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  1. Adel M. Kamal El-Dean
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  2. Ahmed A. Geies
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Correspondence to Eman E. Abd El-Naeem.

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Adel M. Kamal El-Dean, Geies, A.A., Hassanien, R. et al. Novel Synthesis, Reactions, and Biological Study of New Morpholino-Thieno[2,3-c][2,7]Naphthyridines as Anti-Cancer and Anti-Microbial Agents. Russ J Bioorg Chem 48, 821–834 (2022). https://doi.org/10.1134/S1068162022040021

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