New Bioprecursor Prodrugs of Sulfadiazine: Synthesis, X-ray Structure and Hirshfeld Analysis
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, <b>...
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MDPI AG
2022-07-01
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| Series: | Crystals |
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| Online Access: | https://www.mdpi.com/2073-4352/12/8/1016 |
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| author | Mezna Saleh Altowyan Saied M. Soliman Magda M. F. Ismail Matti Haukka Assem Barakat Mohammed Salah Ayoup |
| author_facet | Mezna Saleh Altowyan Saied M. Soliman Magda M. F. Ismail Matti Haukka Assem Barakat Mohammed Salah Ayoup |
| author_sort | Mezna Saleh Altowyan |
| collection | DOAJ |
| description | 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, <b>3,</b> was synthesized via the coupling of diazonium salt of sulfadiazine with ethyl acetoacetate in AcONa at 0 °C. The second prodrug, sulfadiazine-pyrazole, <b>5</b>, was furnished via cyclocondensation of the hydrazono derivative, <b>3</b>, and 2-pyridyl hydrazine, <b>4</b>. The generated data from the X-ray analysis is interpreted and refined to obtain the crystal structure of the target compound, <b>5</b>. 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 <b>5</b> are H···H, O···H and H···C contacts. |
| first_indexed | 2024-03-09T04:34:57Z |
| format | Article |
| id | doaj.art-75f2bd80da44461d9199a461ee09d6dd |
| institution | Directory Open Access Journal |
| issn | 2073-4352 |
| language | English |
| last_indexed | 2024-03-09T04:34:57Z |
| publishDate | 2022-07-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Crystals |
| spelling | doaj.art-75f2bd80da44461d9199a461ee09d6dd2023-12-03T13:29:38ZengMDPI AGCrystals2073-43522022-07-01128101610.3390/cryst12081016New Bioprecursor Prodrugs of Sulfadiazine: Synthesis, X-ray Structure and Hirshfeld AnalysisMezna Saleh Altowyan0Saied M. Soliman1Magda M. F. Ismail2Matti Haukka3Assem Barakat4Mohammed Salah Ayoup5Department of Chemistry, College of Science, Princess Nourah bint Abdulrahman University, P.O. Box 84428, Riyadh 11671, Saudi ArabiaDepartment of Chemistry, Faculty of Science, Alexandria University, P.O. Box 426, Alexandria 21321, EgyptDepartment of Pharmaceutical Medicinal Chemistry, Faculty of Pharmacy (Girls), Al-Azhar University, Cairo 11651, EgyptDepartment of Chemistry, University of Jyväskylä, P.O. Box 35, FI-40014 Jyväskylä, FinlandDepartment of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi ArabiaDepartment of Chemistry, Faculty of Science, Alexandria University, P.O. Box 426, Alexandria 21321, EgyptSulphonamide 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, <b>3,</b> was synthesized via the coupling of diazonium salt of sulfadiazine with ethyl acetoacetate in AcONa at 0 °C. The second prodrug, sulfadiazine-pyrazole, <b>5</b>, was furnished via cyclocondensation of the hydrazono derivative, <b>3</b>, and 2-pyridyl hydrazine, <b>4</b>. The generated data from the X-ray analysis is interpreted and refined to obtain the crystal structure of the target compound, <b>5</b>. 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 <b>5</b> are H···H, O···H and H···C contacts.https://www.mdpi.com/2073-4352/12/8/1016bioprecursor prodrugsulfadiazinecomputational studiesHirshfeld |
| spellingShingle | Mezna Saleh Altowyan Saied M. Soliman Magda M. F. Ismail Matti Haukka Assem Barakat Mohammed Salah Ayoup New Bioprecursor Prodrugs of Sulfadiazine: Synthesis, X-ray Structure and Hirshfeld Analysis Crystals bioprecursor prodrug sulfadiazine computational studies Hirshfeld |
| title | New Bioprecursor Prodrugs of Sulfadiazine: Synthesis, X-ray Structure and Hirshfeld Analysis |
| title_full | New Bioprecursor Prodrugs of Sulfadiazine: Synthesis, X-ray Structure and Hirshfeld Analysis |
| title_fullStr | New Bioprecursor Prodrugs of Sulfadiazine: Synthesis, X-ray Structure and Hirshfeld Analysis |
| title_full_unstemmed | New Bioprecursor Prodrugs of Sulfadiazine: Synthesis, X-ray Structure and Hirshfeld Analysis |
| title_short | New Bioprecursor Prodrugs of Sulfadiazine: Synthesis, X-ray Structure and Hirshfeld Analysis |
| title_sort | new bioprecursor prodrugs of sulfadiazine synthesis x ray structure and hirshfeld analysis |
| topic | bioprecursor prodrug sulfadiazine computational studies Hirshfeld |
| url | https://www.mdpi.com/2073-4352/12/8/1016 |
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