Synthesis, X-ray Single Crystal Structure, Molecular Docking and DFT Computations on N-[(1E)-1-(2H-1,3-Benzodioxol-5-yl)-3-(1H-imidazol-1-yl)propylidene]-hydroxylamine: A New Potential Antifungal Agent Precursor
Mycoses are serious health problem, especially in immunocompromised individuals. A new imidazole-bearing compound containing an oxime functionality was synthesized and characterized with different spectroscopic techniques to be used for the preparation of new antifungal agents. The stereochemistry o...
| Main Authors: | , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2017-02-01
|
| Series: | Molecules |
| Subjects: | |
| Online Access: | http://www.mdpi.com/1420-3049/22/3/373 |
| _version_ | 1830412739576594432 |
|---|---|
| author | Reem I. Al-Wabli Alwah R. Al-Ghamdi Hazem A. Ghabbour Mohamed H. Al-Agamy James Clemy Monicka Issac Hubert Joe Mohamed I. Attia |
| author_facet | Reem I. Al-Wabli Alwah R. Al-Ghamdi Hazem A. Ghabbour Mohamed H. Al-Agamy James Clemy Monicka Issac Hubert Joe Mohamed I. Attia |
| author_sort | Reem I. Al-Wabli |
| collection | DOAJ |
| description | Mycoses are serious health problem, especially in immunocompromised individuals. A new imidazole-bearing compound containing an oxime functionality was synthesized and characterized with different spectroscopic techniques to be used for the preparation of new antifungal agents. The stereochemistry of the oxime double bond was unequivocally determined via the single crystal X-ray technique. The title compound 4, C13H13N3O3·C3H8O, crystallizes in the monoclinic space group P21with a = 9.0963(3) Å, b = 14.7244(6) Å, c = 10.7035(4) Å, β = 94.298 (3)°, V = 1429.57(9) Å3, Z = 2. The molecules were packed in the crystal structure by eight intermolecular hydrogen bond interactions. A comprehensive spectral analysis of the title molecule 4 has been performed based on the scaled quantum mechanical (SQM) force field obtained by density-functional theory (DFT) calculations. A molecular docking study illustrated the binding mode of the title compound 4 into its target protein. The preliminary antifungal activity of the title compound 4 was determined using a broth microdilution assay. |
| first_indexed | 2024-12-20T20:13:21Z |
| format | Article |
| id | doaj.art-d6ad86144e8f42ffb728d7ad4729959a |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-20T20:13:21Z |
| publishDate | 2017-02-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-d6ad86144e8f42ffb728d7ad4729959a2022-12-21T19:27:46ZengMDPI AGMolecules1420-30492017-02-0122337310.3390/molecules22030373molecules22030373Synthesis, X-ray Single Crystal Structure, Molecular Docking and DFT Computations on N-[(1E)-1-(2H-1,3-Benzodioxol-5-yl)-3-(1H-imidazol-1-yl)propylidene]-hydroxylamine: A New Potential Antifungal Agent PrecursorReem I. Al-Wabli0Alwah R. Al-Ghamdi1Hazem A. Ghabbour2Mohamed H. Al-Agamy3James Clemy Monicka4Issac Hubert Joe5Mohamed I. Attia6Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi ArabiaDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi ArabiaDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi ArabiaDepartment of Pharmaceutics, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi ArabiaMuslim Arts College, Thiruvithancode 629174, Tamil Nadu, IndiaCentre for Molecular and Biophysics Research, Mar Ivanios College, Thiruvananthapuram 695015, Kerala, IndiaDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi ArabiaMycoses are serious health problem, especially in immunocompromised individuals. A new imidazole-bearing compound containing an oxime functionality was synthesized and characterized with different spectroscopic techniques to be used for the preparation of new antifungal agents. The stereochemistry of the oxime double bond was unequivocally determined via the single crystal X-ray technique. The title compound 4, C13H13N3O3·C3H8O, crystallizes in the monoclinic space group P21with a = 9.0963(3) Å, b = 14.7244(6) Å, c = 10.7035(4) Å, β = 94.298 (3)°, V = 1429.57(9) Å3, Z = 2. The molecules were packed in the crystal structure by eight intermolecular hydrogen bond interactions. A comprehensive spectral analysis of the title molecule 4 has been performed based on the scaled quantum mechanical (SQM) force field obtained by density-functional theory (DFT) calculations. A molecular docking study illustrated the binding mode of the title compound 4 into its target protein. The preliminary antifungal activity of the title compound 4 was determined using a broth microdilution assay.http://www.mdpi.com/1420-3049/22/3/373crystal structureimidazolebenzodioxoleoximeDFT |
| spellingShingle | Reem I. Al-Wabli Alwah R. Al-Ghamdi Hazem A. Ghabbour Mohamed H. Al-Agamy James Clemy Monicka Issac Hubert Joe Mohamed I. Attia Synthesis, X-ray Single Crystal Structure, Molecular Docking and DFT Computations on N-[(1E)-1-(2H-1,3-Benzodioxol-5-yl)-3-(1H-imidazol-1-yl)propylidene]-hydroxylamine: A New Potential Antifungal Agent Precursor Molecules crystal structure imidazole benzodioxole oxime DFT |
| title | Synthesis, X-ray Single Crystal Structure, Molecular Docking and DFT Computations on N-[(1E)-1-(2H-1,3-Benzodioxol-5-yl)-3-(1H-imidazol-1-yl)propylidene]-hydroxylamine: A New Potential Antifungal Agent Precursor |
| title_full | Synthesis, X-ray Single Crystal Structure, Molecular Docking and DFT Computations on N-[(1E)-1-(2H-1,3-Benzodioxol-5-yl)-3-(1H-imidazol-1-yl)propylidene]-hydroxylamine: A New Potential Antifungal Agent Precursor |
| title_fullStr | Synthesis, X-ray Single Crystal Structure, Molecular Docking and DFT Computations on N-[(1E)-1-(2H-1,3-Benzodioxol-5-yl)-3-(1H-imidazol-1-yl)propylidene]-hydroxylamine: A New Potential Antifungal Agent Precursor |
| title_full_unstemmed | Synthesis, X-ray Single Crystal Structure, Molecular Docking and DFT Computations on N-[(1E)-1-(2H-1,3-Benzodioxol-5-yl)-3-(1H-imidazol-1-yl)propylidene]-hydroxylamine: A New Potential Antifungal Agent Precursor |
| title_short | Synthesis, X-ray Single Crystal Structure, Molecular Docking and DFT Computations on N-[(1E)-1-(2H-1,3-Benzodioxol-5-yl)-3-(1H-imidazol-1-yl)propylidene]-hydroxylamine: A New Potential Antifungal Agent Precursor |
| title_sort | synthesis x ray single crystal structure molecular docking and dft computations on n 1e 1 2h 1 3 benzodioxol 5 yl 3 1h imidazol 1 yl propylidene hydroxylamine a new potential antifungal agent precursor |
| topic | crystal structure imidazole benzodioxole oxime DFT |
| url | http://www.mdpi.com/1420-3049/22/3/373 |
| work_keys_str_mv | AT reemialwabli synthesisxraysinglecrystalstructuremoleculardockinganddftcomputationsonn1e12h13benzodioxol5yl31himidazol1ylpropylidenehydroxylamineanewpotentialantifungalagentprecursor AT alwahralghamdi synthesisxraysinglecrystalstructuremoleculardockinganddftcomputationsonn1e12h13benzodioxol5yl31himidazol1ylpropylidenehydroxylamineanewpotentialantifungalagentprecursor AT hazemaghabbour synthesisxraysinglecrystalstructuremoleculardockinganddftcomputationsonn1e12h13benzodioxol5yl31himidazol1ylpropylidenehydroxylamineanewpotentialantifungalagentprecursor AT mohamedhalagamy synthesisxraysinglecrystalstructuremoleculardockinganddftcomputationsonn1e12h13benzodioxol5yl31himidazol1ylpropylidenehydroxylamineanewpotentialantifungalagentprecursor AT jamesclemymonicka synthesisxraysinglecrystalstructuremoleculardockinganddftcomputationsonn1e12h13benzodioxol5yl31himidazol1ylpropylidenehydroxylamineanewpotentialantifungalagentprecursor AT issachubertjoe synthesisxraysinglecrystalstructuremoleculardockinganddftcomputationsonn1e12h13benzodioxol5yl31himidazol1ylpropylidenehydroxylamineanewpotentialantifungalagentprecursor AT mohamediattia synthesisxraysinglecrystalstructuremoleculardockinganddftcomputationsonn1e12h13benzodioxol5yl31himidazol1ylpropylidenehydroxylamineanewpotentialantifungalagentprecursor |