Preparation and Antibacterial Activity of Some New 4-(2-Heterylidenehydrazinyl)-7-chloroquinoline Derivatives
N-(4-Substituted phenyl)acetamides, which were prepared from acetic anhydride and p-substituted anilines, were utilized as precursors for reactions to Vilsmeier-Haack reagent to form 6-substituted-2-chloroquinoline-3-carbaldehydes 3a–c. Meanwhile, a similar reagent was applied to 1-[1-(4-substituted...
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Wiley
2018-01-01
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| Series: | Journal of Chemistry |
| Online Access: | http://dx.doi.org/10.1155/2018/4301847 |
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| author | Trong Duc Le Ngoc Nam Pham Tien Cong Nguyen |
| author_facet | Trong Duc Le Ngoc Nam Pham Tien Cong Nguyen |
| author_sort | Trong Duc Le |
| collection | DOAJ |
| description | N-(4-Substituted phenyl)acetamides, which were prepared from acetic anhydride and p-substituted anilines, were utilized as precursors for reactions to Vilsmeier-Haack reagent to form 6-substituted-2-chloroquinoline-3-carbaldehydes 3a–c. Meanwhile, a similar reagent was applied to 1-[1-(4-substituted phenyl)ethylidene]-2-phenylhydrazines as substrates, which were synthesized from phenylhydrazine hydrochloride and p-substituted acetophenones, and 1,3-diarylpyrazole-4-carbaldehydes 3d–f were observed as a result. Reactions between the aldehydes 3a–f and 7-chloro-4-hydrazinylquinoline 2, obtained from reaction of 4,7-dichloroquinoline 1 and hydrazine hydrate, formed six new hydrazone compounds, namely, 4-{2-[(6-substituted-2-chloroquinolin-3-yl)methylidene]hydrazinyl}-7-chloroquinolines 4a–c and 4-(2-{[3-(4-substituted phenyl)-1-phenyl-1H-pyrazol-4-yl]methylene}hydrazinyl)-7-chloroquinolines 4d–f. The chemical structures of all synthesized compounds were elucidated by the analysis of IR, 1H, 13C-NMR, and HRMS spectral data. Additionally, all of the synthesized hydrazones were evaluated in terms of cytotoxic activity against four strains of bacteria and four strains of fungus at several concentrations of substrates. As a result, three of them, 4a–c, possess the good ability as growth inhibitor of Bacillus subtilis and Aspergillus niger at the concentration of 25 μg/mL and 50 μg/mL, respectively, while compound 4e only shows a cytotoxic activity against Aspergillus niger at the concentration of 25 μg/mL. |
| format | Article |
| id | doaj-art-1d70e8312bb942a3841aaf23ac42deb5 |
| institution | Kabale University |
| issn | 2090-9063 2090-9071 |
| language | English |
| publishDate | 2018-01-01 |
| publisher | Wiley |
| record_format | Article |
| series | Journal of Chemistry |
| spelling | doaj-art-1d70e8312bb942a3841aaf23ac42deb52025-02-03T05:47:10ZengWileyJournal of Chemistry2090-90632090-90712018-01-01201810.1155/2018/43018474301847Preparation and Antibacterial Activity of Some New 4-(2-Heterylidenehydrazinyl)-7-chloroquinoline DerivativesTrong Duc Le0Ngoc Nam Pham1Tien Cong Nguyen2Department of Chemistry, Ho Chi Minh City University of Education, Ho Chi Minh City 700000, VietnamDepartment of Organic Chemistry, Ho Chi Minh City University of Science, Vietnam National University, Ho Chi Minh City 700000, VietnamDepartment of Chemistry, Ho Chi Minh City University of Education, Ho Chi Minh City 700000, VietnamN-(4-Substituted phenyl)acetamides, which were prepared from acetic anhydride and p-substituted anilines, were utilized as precursors for reactions to Vilsmeier-Haack reagent to form 6-substituted-2-chloroquinoline-3-carbaldehydes 3a–c. Meanwhile, a similar reagent was applied to 1-[1-(4-substituted phenyl)ethylidene]-2-phenylhydrazines as substrates, which were synthesized from phenylhydrazine hydrochloride and p-substituted acetophenones, and 1,3-diarylpyrazole-4-carbaldehydes 3d–f were observed as a result. Reactions between the aldehydes 3a–f and 7-chloro-4-hydrazinylquinoline 2, obtained from reaction of 4,7-dichloroquinoline 1 and hydrazine hydrate, formed six new hydrazone compounds, namely, 4-{2-[(6-substituted-2-chloroquinolin-3-yl)methylidene]hydrazinyl}-7-chloroquinolines 4a–c and 4-(2-{[3-(4-substituted phenyl)-1-phenyl-1H-pyrazol-4-yl]methylene}hydrazinyl)-7-chloroquinolines 4d–f. The chemical structures of all synthesized compounds were elucidated by the analysis of IR, 1H, 13C-NMR, and HRMS spectral data. Additionally, all of the synthesized hydrazones were evaluated in terms of cytotoxic activity against four strains of bacteria and four strains of fungus at several concentrations of substrates. As a result, three of them, 4a–c, possess the good ability as growth inhibitor of Bacillus subtilis and Aspergillus niger at the concentration of 25 μg/mL and 50 μg/mL, respectively, while compound 4e only shows a cytotoxic activity against Aspergillus niger at the concentration of 25 μg/mL.http://dx.doi.org/10.1155/2018/4301847 |
| spellingShingle | Trong Duc Le Ngoc Nam Pham Tien Cong Nguyen Preparation and Antibacterial Activity of Some New 4-(2-Heterylidenehydrazinyl)-7-chloroquinoline Derivatives Journal of Chemistry |
| title | Preparation and Antibacterial Activity of Some New 4-(2-Heterylidenehydrazinyl)-7-chloroquinoline Derivatives |
| title_full | Preparation and Antibacterial Activity of Some New 4-(2-Heterylidenehydrazinyl)-7-chloroquinoline Derivatives |
| title_fullStr | Preparation and Antibacterial Activity of Some New 4-(2-Heterylidenehydrazinyl)-7-chloroquinoline Derivatives |
| title_full_unstemmed | Preparation and Antibacterial Activity of Some New 4-(2-Heterylidenehydrazinyl)-7-chloroquinoline Derivatives |
| title_short | Preparation and Antibacterial Activity of Some New 4-(2-Heterylidenehydrazinyl)-7-chloroquinoline Derivatives |
| title_sort | preparation and antibacterial activity of some new 4 2 heterylidenehydrazinyl 7 chloroquinoline derivatives |
| url | http://dx.doi.org/10.1155/2018/4301847 |
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