Synthesis, X-ray crystallography and antimicrobial activity of 2-cyanoguanidinophenytoin
Abstract The optimized synthesis of [5-oxo-4,4-diphenylimidazolidin-2-ylidene]cyanamide, which is known as 2-cyanoguanidinophenytoin (CNG-DPH) (3), and (imidazo[4,5-d]imidazole-2,5-diylidine)dicyanamide (4) has been reported in the present work. Furthermore, new Mannich bases derived from CNG-DPH we...
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| Format: | Article |
| Language: | English |
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Nature Portfolio
2023-11-01
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| Series: | Scientific Reports |
| Online Access: | https://doi.org/10.1038/s41598-023-45533-1 |
| _version_ | 1797630145136164864 |
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| author | Ahmed F. Mabied Amr H. Moustafa Antar A. Abdelhamid Taha M. Tiama Amer A. Amer |
| author_facet | Ahmed F. Mabied Amr H. Moustafa Antar A. Abdelhamid Taha M. Tiama Amer A. Amer |
| author_sort | Ahmed F. Mabied |
| collection | DOAJ |
| description | Abstract The optimized synthesis of [5-oxo-4,4-diphenylimidazolidin-2-ylidene]cyanamide, which is known as 2-cyanoguanidinophenytoin (CNG-DPH) (3), and (imidazo[4,5-d]imidazole-2,5-diylidine)dicyanamide (4) has been reported in the present work. Furthermore, new Mannich bases derived from CNG-DPH were synthesized via its reaction with formaldehyde and using the corresponding amines, piperidine (base 5), and morpholine (base 6). Also, the antimicrobial activity and X-ray crystal structures for CNG-DPH and their Mannich bases were studied. The bases 3 and 6 crystallized in a monoclinic system; the crystal structure of 3 containing four molecules in the unit cell with a P21/c space group. The unit cell of 6 has eight molecules with a C2/c space group. The inter and intra hydrogen bond contacts packed and stabilized both of the structures. The morpholine ring of base 6 demonstrated a distinctive chair configuration. Mannich bases 5 and 6 showed promising antimicrobial effects. base 4 has a greater percentage for in vitro cytotoxicity (IC50) against normal cells, whereas 3 has the lowest ratio. |
| first_indexed | 2024-03-11T11:04:00Z |
| format | Article |
| id | doaj.art-020acf1f9b034cb0b568a118239c94a6 |
| institution | Directory Open Access Journal |
| issn | 2045-2322 |
| language | English |
| last_indexed | 2024-03-11T11:04:00Z |
| publishDate | 2023-11-01 |
| publisher | Nature Portfolio |
| record_format | Article |
| series | Scientific Reports |
| spelling | doaj.art-020acf1f9b034cb0b568a118239c94a62023-11-12T12:18:16ZengNature PortfolioScientific Reports2045-23222023-11-0113111210.1038/s41598-023-45533-1Synthesis, X-ray crystallography and antimicrobial activity of 2-cyanoguanidinophenytoinAhmed F. Mabied0Amr H. Moustafa1Antar A. Abdelhamid2Taha M. Tiama3Amer A. Amer4X-Ray Crystallography Lab., Solid State Physics Department, National Research CentreDepartment of Chemistry, Faculty of Science, Sohag UniversityDepartment of Chemistry, Faculty of Science, Sohag UniversityDepartment of Basic Sciences, October High Institute of Engineering & Technology - OHIDepartment of Chemistry, Faculty of Science, Sohag UniversityAbstract The optimized synthesis of [5-oxo-4,4-diphenylimidazolidin-2-ylidene]cyanamide, which is known as 2-cyanoguanidinophenytoin (CNG-DPH) (3), and (imidazo[4,5-d]imidazole-2,5-diylidine)dicyanamide (4) has been reported in the present work. Furthermore, new Mannich bases derived from CNG-DPH were synthesized via its reaction with formaldehyde and using the corresponding amines, piperidine (base 5), and morpholine (base 6). Also, the antimicrobial activity and X-ray crystal structures for CNG-DPH and their Mannich bases were studied. The bases 3 and 6 crystallized in a monoclinic system; the crystal structure of 3 containing four molecules in the unit cell with a P21/c space group. The unit cell of 6 has eight molecules with a C2/c space group. The inter and intra hydrogen bond contacts packed and stabilized both of the structures. The morpholine ring of base 6 demonstrated a distinctive chair configuration. Mannich bases 5 and 6 showed promising antimicrobial effects. base 4 has a greater percentage for in vitro cytotoxicity (IC50) against normal cells, whereas 3 has the lowest ratio.https://doi.org/10.1038/s41598-023-45533-1 |
| spellingShingle | Ahmed F. Mabied Amr H. Moustafa Antar A. Abdelhamid Taha M. Tiama Amer A. Amer Synthesis, X-ray crystallography and antimicrobial activity of 2-cyanoguanidinophenytoin Scientific Reports |
| title | Synthesis, X-ray crystallography and antimicrobial activity of 2-cyanoguanidinophenytoin |
| title_full | Synthesis, X-ray crystallography and antimicrobial activity of 2-cyanoguanidinophenytoin |
| title_fullStr | Synthesis, X-ray crystallography and antimicrobial activity of 2-cyanoguanidinophenytoin |
| title_full_unstemmed | Synthesis, X-ray crystallography and antimicrobial activity of 2-cyanoguanidinophenytoin |
| title_short | Synthesis, X-ray crystallography and antimicrobial activity of 2-cyanoguanidinophenytoin |
| title_sort | synthesis x ray crystallography and antimicrobial activity of 2 cyanoguanidinophenytoin |
| url | https://doi.org/10.1038/s41598-023-45533-1 |
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