Synthesis, crystal structure, hirshfeld study, DFT analysis, molecular docking study, antimicrobial activity of β-enaminonitrile bearing 1H-pyran
Abstract 3-Amino-1-(3,4-dimethoxyphenyl)-8-methoxy-1H-benzo[f]chromene-2-carbonitrile (3-ABC, 4) was prepared and affirmed through the spectral data and single crystal X-rays diffraction. The molecule spatial attributes were revealed by the three-dimensional Hirshfeld surface, which is validated by...
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| Format: | Article |
| Language: | English |
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Springer
2025-01-01
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| Series: | Discover Applied Sciences |
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| Online Access: | https://doi.org/10.1007/s42452-024-06254-w |
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| author | Al-Anood M. Al-Dies Fawzia F. Alblewi Rawda M. Okasha Mosa H. Alsehli Rita M. A. Borik Saleh Ihmaid Abd El-Galil E. Amr Hazem A. Ghabbour Ahmed A. Elhenawy Ahmed M. El-Agrody |
| author_facet | Al-Anood M. Al-Dies Fawzia F. Alblewi Rawda M. Okasha Mosa H. Alsehli Rita M. A. Borik Saleh Ihmaid Abd El-Galil E. Amr Hazem A. Ghabbour Ahmed A. Elhenawy Ahmed M. El-Agrody |
| author_sort | Al-Anood M. Al-Dies |
| collection | DOAJ |
| description | Abstract 3-Amino-1-(3,4-dimethoxyphenyl)-8-methoxy-1H-benzo[f]chromene-2-carbonitrile (3-ABC, 4) was prepared and affirmed through the spectral data and single crystal X-rays diffraction. The molecule spatial attributes were revealed by the three-dimensional Hirshfeld surface, which is validated by comprehensive statistical evaluations. The key interactions that contribute to the crystal's stability and properties, such as π–π stacking and H⋯X contacts, were highlighted. The dominant forces in the crystal were explained by energy framework calculations and density functional theory analyses, which also show the geometric optimization aspects and molecular reactivity indicators. The focus is on the investigation of frontier molecular orbitals, aromaticity, and π–π stacking abilities. The research concluded by identifying electron density distributions, aromatic features, and possible reactivity sites, offering a complete picture of the compound's structural and electronic landscape. Compound 4 was screened for its antimicrobial capability against three Gram-positive, three Gram-negative bacteria, and three fungi, utilizing the reference antibiotic drug Ampicillin, Gentamycin, and Ketoconazole. Compound 4 exhibited favorable antimicrobial activities that were lower/resembled the reference antimicrobial agents with an IZ range of 15–31 mm. In addition, MIC, MBC, and MFC were assessed and screened for the target molecule 4, unveiling its revealing antimicrobial activities. Lastly, the molecular docking evaluation was implemented for the molecules interaction with the DHFR protein. The compounds exhibit significant interactions with the EGFR protein's active site. |
| format | Article |
| id | doaj-art-f5eef3f0fd3b4ff29137732526958a6c |
| institution | Kabale University |
| issn | 3004-9261 |
| language | English |
| publishDate | 2025-01-01 |
| publisher | Springer |
| record_format | Article |
| series | Discover Applied Sciences |
| spelling | doaj-art-f5eef3f0fd3b4ff29137732526958a6c2025-01-12T12:35:13ZengSpringerDiscover Applied Sciences3004-92612025-01-017112410.1007/s42452-024-06254-wSynthesis, crystal structure, hirshfeld study, DFT analysis, molecular docking study, antimicrobial activity of β-enaminonitrile bearing 1H-pyranAl-Anood M. Al-Dies0Fawzia F. Alblewi1Rawda M. Okasha2Mosa H. Alsehli3Rita M. A. Borik4Saleh Ihmaid5Abd El-Galil E. Amr6Hazem A. Ghabbour7Ahmed A. Elhenawy8Ahmed M. El-Agrody9Chemistry Department, Umm Al-Qura University, Al-Qunfudah University CollegeChemistry Department, College of Science, Taibah UniversityChemistry Department, College of Science, Taibah UniversityChemistry Department, College of Science, Taibah UniversityDepartment of Physical Sciences, Chemistry Division, College of Science, Jazan UniversityDepartment of Pharmaceutical Chemistry, College of Pharmacy, Jerash UniversityApplied Organic Chemistry Department, National Research CenterDepartment of Medicinal Chemistry, Faculty of Pharmacy, University of MansouraChemistry Department, Faculty of Science, Al-Azhar UniversityChemistry Department, Faculty of Science, Al-Azhar UniversityAbstract 3-Amino-1-(3,4-dimethoxyphenyl)-8-methoxy-1H-benzo[f]chromene-2-carbonitrile (3-ABC, 4) was prepared and affirmed through the spectral data and single crystal X-rays diffraction. The molecule spatial attributes were revealed by the three-dimensional Hirshfeld surface, which is validated by comprehensive statistical evaluations. The key interactions that contribute to the crystal's stability and properties, such as π–π stacking and H⋯X contacts, were highlighted. The dominant forces in the crystal were explained by energy framework calculations and density functional theory analyses, which also show the geometric optimization aspects and molecular reactivity indicators. The focus is on the investigation of frontier molecular orbitals, aromaticity, and π–π stacking abilities. The research concluded by identifying electron density distributions, aromatic features, and possible reactivity sites, offering a complete picture of the compound's structural and electronic landscape. Compound 4 was screened for its antimicrobial capability against three Gram-positive, three Gram-negative bacteria, and three fungi, utilizing the reference antibiotic drug Ampicillin, Gentamycin, and Ketoconazole. Compound 4 exhibited favorable antimicrobial activities that were lower/resembled the reference antimicrobial agents with an IZ range of 15–31 mm. In addition, MIC, MBC, and MFC were assessed and screened for the target molecule 4, unveiling its revealing antimicrobial activities. Lastly, the molecular docking evaluation was implemented for the molecules interaction with the DHFR protein. The compounds exhibit significant interactions with the EGFR protein's active site.https://doi.org/10.1007/s42452-024-06254-w1H-Benzo[f]chromeneX-rayAntimicrobial activityDensity functional theoryDocking study |
| spellingShingle | Al-Anood M. Al-Dies Fawzia F. Alblewi Rawda M. Okasha Mosa H. Alsehli Rita M. A. Borik Saleh Ihmaid Abd El-Galil E. Amr Hazem A. Ghabbour Ahmed A. Elhenawy Ahmed M. El-Agrody Synthesis, crystal structure, hirshfeld study, DFT analysis, molecular docking study, antimicrobial activity of β-enaminonitrile bearing 1H-pyran Discover Applied Sciences 1H-Benzo[f]chromene X-ray Antimicrobial activity Density functional theory Docking study |
| title | Synthesis, crystal structure, hirshfeld study, DFT analysis, molecular docking study, antimicrobial activity of β-enaminonitrile bearing 1H-pyran |
| title_full | Synthesis, crystal structure, hirshfeld study, DFT analysis, molecular docking study, antimicrobial activity of β-enaminonitrile bearing 1H-pyran |
| title_fullStr | Synthesis, crystal structure, hirshfeld study, DFT analysis, molecular docking study, antimicrobial activity of β-enaminonitrile bearing 1H-pyran |
| title_full_unstemmed | Synthesis, crystal structure, hirshfeld study, DFT analysis, molecular docking study, antimicrobial activity of β-enaminonitrile bearing 1H-pyran |
| title_short | Synthesis, crystal structure, hirshfeld study, DFT analysis, molecular docking study, antimicrobial activity of β-enaminonitrile bearing 1H-pyran |
| title_sort | synthesis crystal structure hirshfeld study dft analysis molecular docking study antimicrobial activity of β enaminonitrile bearing 1h pyran |
| topic | 1H-Benzo[f]chromene X-ray Antimicrobial activity Density functional theory Docking study |
| url | https://doi.org/10.1007/s42452-024-06254-w |
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