Synthesis and Evaluation of Novel Fluorinated 2-Styrylchromones as Antibacterial Agents
A range of fluorinated 2-styrylchromones (5a–g) of which six were new (5a–f) were prepared in three steps using the Baker-Venkataraman rearrangement along with two methoxylated derivatives (5h-i) and a methylenedioxy derivative (5j) and screened for their antibacterial activity using Gram-positive b...
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| Format: | Article |
| Language: | English |
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Wiley
2013-01-01
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| Series: | Journal of Chemistry |
| Online Access: | http://dx.doi.org/10.1155/2013/436758 |
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| author | Mehbub Momin Deresh Ramjugernath Hafizah Chenia Neil A. Koorbanally |
| author_facet | Mehbub Momin Deresh Ramjugernath Hafizah Chenia Neil A. Koorbanally |
| author_sort | Mehbub Momin |
| collection | DOAJ |
| description | A range of fluorinated 2-styrylchromones (5a–g) of which six were new (5a–f) were prepared in three steps using the Baker-Venkataraman rearrangement along with two methoxylated derivatives (5h-i) and a methylenedioxy derivative (5j) and screened for their antibacterial activity using Gram-positive bacteria (Staphylococcus aureus, sciuri, and xylosus as well as Bacillus subtilis) and Gram-negative bacteria (Escherichia coli, Pseudomonas aeruginosa, and Klebsiella pneumonia). The compounds were most effective against B. subtilis followed by S. aureus and a single strain of E. coli (ATCC 25922). Difluorination on the phenyl ring was shown to enhance antibacterial activity, and fluorine substitution at the 6 position was shown to be far superior to substitution at the 7 position. In comparison to tetracycline, the activity indices of the fluorinated styrylchromones ranged from 0.50 to 0.75 against B. subtilis. The crystal structure of 2′-fluoro-2-styrylchromone is also presented, and the molecule was shown to be planar. |
| format | Article |
| id | doaj-art-eb606633891644a98bbb75a6ed7f9cbf |
| institution | Kabale University |
| issn | 2090-9063 2090-9071 |
| language | English |
| publishDate | 2013-01-01 |
| publisher | Wiley |
| record_format | Article |
| series | Journal of Chemistry |
| spelling | doaj-art-eb606633891644a98bbb75a6ed7f9cbf2025-02-03T01:23:45ZengWileyJournal of Chemistry2090-90632090-90712013-01-01201310.1155/2013/436758436758Synthesis and Evaluation of Novel Fluorinated 2-Styrylchromones as Antibacterial AgentsMehbub Momin0Deresh Ramjugernath1Hafizah Chenia2Neil A. Koorbanally3School of Chemistry, University of KwaZulu-Natal, Private Bag X54001, Durban 4000, South AfricaSchool of Chemical Engineering, University of KwaZulu-Natal, Private Bag X54001, Durban 4000, South AfricaDepartment of Biochemistry, Genetics, and Microbiology, University of KwaZulu-Natal, Private Bag X54001, Durban 4000, South AfricaSchool of Chemistry, University of KwaZulu-Natal, Private Bag X54001, Durban 4000, South AfricaA range of fluorinated 2-styrylchromones (5a–g) of which six were new (5a–f) were prepared in three steps using the Baker-Venkataraman rearrangement along with two methoxylated derivatives (5h-i) and a methylenedioxy derivative (5j) and screened for their antibacterial activity using Gram-positive bacteria (Staphylococcus aureus, sciuri, and xylosus as well as Bacillus subtilis) and Gram-negative bacteria (Escherichia coli, Pseudomonas aeruginosa, and Klebsiella pneumonia). The compounds were most effective against B. subtilis followed by S. aureus and a single strain of E. coli (ATCC 25922). Difluorination on the phenyl ring was shown to enhance antibacterial activity, and fluorine substitution at the 6 position was shown to be far superior to substitution at the 7 position. In comparison to tetracycline, the activity indices of the fluorinated styrylchromones ranged from 0.50 to 0.75 against B. subtilis. The crystal structure of 2′-fluoro-2-styrylchromone is also presented, and the molecule was shown to be planar.http://dx.doi.org/10.1155/2013/436758 |
| spellingShingle | Mehbub Momin Deresh Ramjugernath Hafizah Chenia Neil A. Koorbanally Synthesis and Evaluation of Novel Fluorinated 2-Styrylchromones as Antibacterial Agents Journal of Chemistry |
| title | Synthesis and Evaluation of Novel Fluorinated 2-Styrylchromones as Antibacterial Agents |
| title_full | Synthesis and Evaluation of Novel Fluorinated 2-Styrylchromones as Antibacterial Agents |
| title_fullStr | Synthesis and Evaluation of Novel Fluorinated 2-Styrylchromones as Antibacterial Agents |
| title_full_unstemmed | Synthesis and Evaluation of Novel Fluorinated 2-Styrylchromones as Antibacterial Agents |
| title_short | Synthesis and Evaluation of Novel Fluorinated 2-Styrylchromones as Antibacterial Agents |
| title_sort | synthesis and evaluation of novel fluorinated 2 styrylchromones as antibacterial agents |
| url | http://dx.doi.org/10.1155/2013/436758 |
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