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Crystal structure, Hirshfeld surface analysis, computational and antifungal studies of dihydropyrimidines on the basis of salicylaldehyde derivatives

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Abstract

We herein reported the synthesis of dihydropyrimidines 1 and 2 on the basis of nitro and brominated salicylaldehyde derivatives by Biginelli reaction in microwave conditions in the presence of cheap low toxic copper triflate. The structures of both compounds were investigated by the X-ray single-crystal diffraction method. The presence of non-covalent interactions and their impact on crystal structure was determined. In addition, the conformation of the dihydropyrimidine ring was also studied. In order to understand the molecular interactions in their structure, the Hirshfeld surface and contacts enrichment analyses were performed. Moreover, the biological activity of synthesized compounds was also investigated against Candida albicans and Aspergillus niger fungi. Finally, computational studies of the related compounds were performed at M062X/6-31G(d) level in the water and molecular docking calculations were done against the thymidylate kinase of Candida albicans.

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Acknowledgements

This study was made possible by TUBITAK ULAKBIM, High Performance and Grid Computing Center (TR-Grid e-Infrastructure).

Funding

This work was supported by the Erasmus + overseas/ICM KA107 programme, Science Development Foundation under the President of the Republic of Azerbaijan and TUBITAK in the frames of the project number EIF-BGM-5-AZTURK-1/2018-2/02/4-M-02 and the Scientific Research Project Fund of Sivas Cumhuriyet University under Project Number RGD-020.

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Authors and Affiliations

  1. Baku State University, ICRL, Z. Khalilov 23, Baku, AZ 1148, Azerbaijan

    Alakbar Huseynzada, Haji Vahid Akhundzada & Ulviyya Hasanova

  2. Université de Lorraine, CNRS, CRM2, 54000, Nancy, France

    Christian Jelsch

  3. Institute of Radiation Problems of ANAS, B. Vahabzada 9, Baku, AZ 1143, Azerbaijan

    Haji Vahid Akhundzada

  4. Laboratoire de Chimie des Matériaux, Faculté des Sciences de Bizerte, Université de Carthage, 7021, Zarzouna, Tunisia

    Sarra Soudani & Cherif Ben Nasr

  5. Chemistry Department, Sivas Cumhuriyet University, Sivas, Turkey

    Koray Sayin

  6. LC-MS Laboratory, Advanced Technology Research and Application Center, Sivas Cumhuriyet University, Sivas, Turkey

    Mustafa Demiralp

  7. Nanoresearch Center, Baku State University, Z. Khalilov 23, Baku, AZ 1148, Azerbaijan

    Goncha Eyvazova

  8. Geotechnological Problems of Oil, Gas and Chemistry, Azerbaijan State Oil and Industry University, Baku, Azerbaijan

    Alakbar Huseynzada, Haji Vahid Akhundzada, Ulviyya Hasanova & Zarema Gakhramanova

  9. Institute of Petrochemical Processes, K. Avenue 30, Baku, AZ 1005, Azerbaijan

    Vagif Abbasov

  10. Chemistry Department, Azerbaijan Engineers Union, Bashir Safaroglu 118, Baku, Azerbaijan

    Alakbar Huseynzada

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  1. Alakbar Huseynzada
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  2. Christian Jelsch
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Correspondence to Alakbar Huseynzada.

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Huseynzada, A., Jelsch, C., Akhundzada, H.V. et al. Crystal structure, Hirshfeld surface analysis, computational and antifungal studies of dihydropyrimidines on the basis of salicylaldehyde derivatives. J IRAN CHEM SOC 20, 109–123 (2023). https://doi.org/10.1007/s13738-022-02659-9

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