(2<i>E</i>)-2-[1-(1,3-Benzodioxol-5-yl)-3-(1<i>H</i>-imidazol-1-yl)propylidene]-<i>N</i>-(2-chlorophenyl)hydrazine carboxamide: Synthesis, X-ray Structure, Hirshfeld Surface Analysis, DFT Calculations, Molecular Docking and Antifungal Profile
Life-threatening fungal infections accounts for a major global health burden especially for individuals suffering from cancer, acquired immune deficiency syndrome (AIDS), or autoimmune diseases. (2<i>E</i>)-2-[1-(1,3-Benzodioxol-5-yl)-3-(1<i>H</i>-imidazol-1-yl)propylidene]-&...
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| Format: | Article |
| Language: | English |
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MDPI AG
2019-02-01
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| Series: | Crystals |
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| Online Access: | https://www.mdpi.com/2073-4352/9/2/82 |
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| author | Reem I. Al-Wabli Alwah R. Al-Ghamdi Suchindra Amma Vijayakumar Aswathy Hazem A. Ghabbour Mohamed H. Al-Agamy Issac Hubert Joe Mohamed I. Attia |
| author_facet | Reem I. Al-Wabli Alwah R. Al-Ghamdi Suchindra Amma Vijayakumar Aswathy Hazem A. Ghabbour Mohamed H. Al-Agamy Issac Hubert Joe Mohamed I. Attia |
| author_sort | Reem I. Al-Wabli |
| collection | DOAJ |
| description | Life-threatening fungal infections accounts for a major global health burden especially for individuals suffering from cancer, acquired immune deficiency syndrome (AIDS), or autoimmune diseases. (2<i>E</i>)-2-[1-(1,3-Benzodioxol-5-yl)-3-(1<i>H</i>-imidazol-1-yl)propylidene]-<i>N</i>-(2-chlorophenyl)hydrazinecarboxamide has been synthesized and characterized using various spectroscopic tools to be evaluated as a new antifungal agent. The (<i>E</i>)-configuration of the imine moiety of the title molecule has been unequivocally identified with the aid of single crystal X-ray analysis. The molecular structure of compound <b>4</b> was crystallized in the monoclinic, <i>P</i>2<sub>1</sub>/c, <i>a</i> = 8.7780 (6) Å, <i>b</i> = 20.5417 (15) Å, <i>c</i> = 11.0793 (9) Å, <i>β</i> = 100.774 (2)°, <i>V</i> = 1962.5 (3) Å<sup>3</sup>, and <i>Z</i> = 4. Density functional theory computations have thoroughly explored the electronic characteristics of the title molecule. Moreover, molecular docking studies and Hirshfeld surface analysis were also executed on the title compound <b>4</b>. The in vitro antifungal potential of the target compound was examined against four different fungal strains. |
| first_indexed | 2024-04-11T20:47:12Z |
| format | Article |
| id | doaj.art-8e4bff6076054300bb564fafff82a7ae |
| institution | Directory Open Access Journal |
| issn | 2073-4352 |
| language | English |
| last_indexed | 2024-04-11T20:47:12Z |
| publishDate | 2019-02-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Crystals |
| spelling | doaj.art-8e4bff6076054300bb564fafff82a7ae2022-12-22T04:03:58ZengMDPI AGCrystals2073-43522019-02-01928210.3390/cryst9020082cryst9020082(2<i>E</i>)-2-[1-(1,3-Benzodioxol-5-yl)-3-(1<i>H</i>-imidazol-1-yl)propylidene]-<i>N</i>-(2-chlorophenyl)hydrazine carboxamide: Synthesis, X-ray Structure, Hirshfeld Surface Analysis, DFT Calculations, Molecular Docking and Antifungal ProfileReem I. Al-Wabli0Alwah R. Al-Ghamdi1Suchindra Amma Vijayakumar Aswathy2Hazem A. Ghabbour3Mohamed H. Al-Agamy4Issac 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 ArabiaCenter for Molecular Biophysics Research, Mar Ivanios College, Nalanchira, Thiruvanthapuram 695015, IndiaDepartment of Medicinal Chemistry, Faculty of Pharmacy, Mansoura University, Mansoura 35516, EgyptDepartment of Pharmaceutics, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi ArabiaCenter for Molecular Biophysics Research, Mar Ivanios College, Nalanchira, Thiruvanthapuram 695015, IndiaDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi ArabiaLife-threatening fungal infections accounts for a major global health burden especially for individuals suffering from cancer, acquired immune deficiency syndrome (AIDS), or autoimmune diseases. (2<i>E</i>)-2-[1-(1,3-Benzodioxol-5-yl)-3-(1<i>H</i>-imidazol-1-yl)propylidene]-<i>N</i>-(2-chlorophenyl)hydrazinecarboxamide has been synthesized and characterized using various spectroscopic tools to be evaluated as a new antifungal agent. The (<i>E</i>)-configuration of the imine moiety of the title molecule has been unequivocally identified with the aid of single crystal X-ray analysis. The molecular structure of compound <b>4</b> was crystallized in the monoclinic, <i>P</i>2<sub>1</sub>/c, <i>a</i> = 8.7780 (6) Å, <i>b</i> = 20.5417 (15) Å, <i>c</i> = 11.0793 (9) Å, <i>β</i> = 100.774 (2)°, <i>V</i> = 1962.5 (3) Å<sup>3</sup>, and <i>Z</i> = 4. Density functional theory computations have thoroughly explored the electronic characteristics of the title molecule. Moreover, molecular docking studies and Hirshfeld surface analysis were also executed on the title compound <b>4</b>. The in vitro antifungal potential of the target compound was examined against four different fungal strains.https://www.mdpi.com/2073-4352/9/2/82Crystal structureImidazoleBenzodioxoleSemicarbazoneDFT |
| spellingShingle | Reem I. Al-Wabli Alwah R. Al-Ghamdi Suchindra Amma Vijayakumar Aswathy Hazem A. Ghabbour Mohamed H. Al-Agamy Issac Hubert Joe Mohamed I. Attia (2<i>E</i>)-2-[1-(1,3-Benzodioxol-5-yl)-3-(1<i>H</i>-imidazol-1-yl)propylidene]-<i>N</i>-(2-chlorophenyl)hydrazine carboxamide: Synthesis, X-ray Structure, Hirshfeld Surface Analysis, DFT Calculations, Molecular Docking and Antifungal Profile Crystals Crystal structure Imidazole Benzodioxole Semicarbazone DFT |
| title | (2<i>E</i>)-2-[1-(1,3-Benzodioxol-5-yl)-3-(1<i>H</i>-imidazol-1-yl)propylidene]-<i>N</i>-(2-chlorophenyl)hydrazine carboxamide: Synthesis, X-ray Structure, Hirshfeld Surface Analysis, DFT Calculations, Molecular Docking and Antifungal Profile |
| title_full | (2<i>E</i>)-2-[1-(1,3-Benzodioxol-5-yl)-3-(1<i>H</i>-imidazol-1-yl)propylidene]-<i>N</i>-(2-chlorophenyl)hydrazine carboxamide: Synthesis, X-ray Structure, Hirshfeld Surface Analysis, DFT Calculations, Molecular Docking and Antifungal Profile |
| title_fullStr | (2<i>E</i>)-2-[1-(1,3-Benzodioxol-5-yl)-3-(1<i>H</i>-imidazol-1-yl)propylidene]-<i>N</i>-(2-chlorophenyl)hydrazine carboxamide: Synthesis, X-ray Structure, Hirshfeld Surface Analysis, DFT Calculations, Molecular Docking and Antifungal Profile |
| title_full_unstemmed | (2<i>E</i>)-2-[1-(1,3-Benzodioxol-5-yl)-3-(1<i>H</i>-imidazol-1-yl)propylidene]-<i>N</i>-(2-chlorophenyl)hydrazine carboxamide: Synthesis, X-ray Structure, Hirshfeld Surface Analysis, DFT Calculations, Molecular Docking and Antifungal Profile |
| title_short | (2<i>E</i>)-2-[1-(1,3-Benzodioxol-5-yl)-3-(1<i>H</i>-imidazol-1-yl)propylidene]-<i>N</i>-(2-chlorophenyl)hydrazine carboxamide: Synthesis, X-ray Structure, Hirshfeld Surface Analysis, DFT Calculations, Molecular Docking and Antifungal Profile |
| title_sort | 2 i e i 2 1 1 3 benzodioxol 5 yl 3 1 i h i imidazol 1 yl propylidene i n i 2 chlorophenyl hydrazine carboxamide synthesis x ray structure hirshfeld surface analysis dft calculations molecular docking and antifungal profile |
| topic | Crystal structure Imidazole Benzodioxole Semicarbazone DFT |
| url | https://www.mdpi.com/2073-4352/9/2/82 |
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