A1 Journal article (refereed)
New Bioprecursor Prodrugs of Sulfadiazine : Synthesis, X-ray Structure and Hirshfeld Analysis (2022)

Altowyan, M. S., Soliman, S. M., Ismail, M. M. F., Haukka, M., Barakat, A., & Ayoup, M. S. (2022). New Bioprecursor Prodrugs of Sulfadiazine : Synthesis, X-ray Structure and Hirshfeld Analysis. Crystals, 12(8), Article 1016. https://doi.org/10.3390/cryst12081016

JYU authors or editors

Publication details

All authors or editors: Altowyan, Mezna Saleh; Soliman, Saied M.; Ismail, Magda M. F.; Haukka, Matti; Barakat, Assem; Ayoup, Mohammed Salah

Journal or series: Crystals

eISSN: 2073-4352

Publication year: 2022

Publication date: 22/07/2022

Volume: 12

Issue number: 8

Article number: 1016

Publisher: MDPI AG

Publication country: Switzerland

Publication language: English

DOI: https://doi.org/10.3390/cryst12081016

Publication open access: Openly available

Publication channel open access: Open Access channel

Publication is parallel published (JYX): https://jyx.jyu.fi/handle/123456789/83295

Abstract

Sulphonamide motif is found extensively in numerous chemotherapeutic drug candidates, it acts by stopping the production of folate inside the bacterial cell. Current research has established the synthesis and characterization of new bioprecursor prodrugs of sulfadiazine. The first prodrug, 3, was synthesized via the coupling of diazonium salt of sulfadiazine with ethyl acetoacetate in AcONa at 0 °C. The second prodrug, sulfadiazine-pyrazole, 5, was furnished via cyclocondensation of the hydrazono derivative, 3, and 2-pyridyl hydrazine, 4. The generated data from the X-ray analysis is interpreted and refined to obtain the crystal structure of the target compound, 5. Density functional theory (DFT) method was used to calculate the optimized geometrical parameters, electronic state (HOMO–LUMO), and the electronic properties. Moreover, Hirshfeld analysis revealed that the most important contributions to the crystal packing of the prodrug 5 are H···H, O···H and H···C contacts.

Keywords: medicinal substances; antibiotics; antimicrobial compounds; prodrugs; chemical synthesis; x-ray crystallography

Free keywords: bioprecursor prodrug; sulfadiazine; computational studies; Hirshfeld

Contributing organizations

Ministry reporting: Yes

VIRTA submission year: 2022

JUFO rating: 1