Synthesis, Characterization, and Antibacterial Activity of Novel Mutual Non-Steroidal Anti-inflammatory Prodrugs
Non steroidal anti-inflammatory drugs (NSAIDs) are among the most used analgesic and anti-inflammatory drugs. However inhibition of cyclooxygenase1 and acidic groups such as carboxylic groups in most NSAIDs cause gastrointestinal (GI) side effects. Therefore masking the acidic groups till it pass th...
| Main Authors: | , |
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| Format: | Article |
| Language: | English |
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Salahaddin University-Erbil
2019-12-01
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| Series: | Zanco Journal of Pure and Applied Sciences |
| Subjects: | |
| Online Access: | https://zancojournals.su.edu.krd/index.php/JPAS/article/view/2680 |
| _version_ | 1819107867690532864 |
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| author | Banaz mohammed hamadameen Dana M. Hamad Ameen |
| author_facet | Banaz mohammed hamadameen Dana M. Hamad Ameen |
| author_sort | Banaz mohammed hamadameen |
| collection | DOAJ |
| description | Non steroidal anti-inflammatory drugs (NSAIDs) are among the most used analgesic and anti-inflammatory drugs. However inhibition of cyclooxygenase1 and acidic groups such as carboxylic groups in most NSAIDs cause gastrointestinal (GI) side effects. Therefore masking the acidic groups till it pass through the GI tract will decrease the direct GI side effects and because N-(2,6-dimethylphenyl)-acetamide 1 also has anti-inflammatory activity so the synthesized ester prodrugs might act as mutual prodrugs. Moreover, because of emerging of new strains of bacteria and resistance of bacteria to the available antibacterial agents, new antibacterial agents are needed. The NSAIDs have antibacterial activity and N-(2,6-dimethylphenyl) acetamide 1 also has antibacterial activity so binding of these molecules with each other might give more potent antibacterial agent. 2-Chloro-N-(2,6-dimethyl phenyl) acetamide 1 was utilized to synthesize ester prodrug of various NSAIDs 2a-f. The 2-Chloro-N-(2,6-dimethylphenyl)-acetamide 1 undergo substitution reaction at α position with various sodium carboxylate of NSAIDs 2a-f in DMSO. The constitution of the newly synthesized ester prodrugs of NSAIDs 3a-f had been confirmed on the basis of their IR, ¹H and ¹³C-NMR spectral data. All the synthesized ester prodrugs 3a-f were screened for their in vitro antibacterial activities against Staphylococcus aureus ATCC 25923 and Escherichia coli ATCC 25922 however, their antibacterial activity decreased compared with their starting 1 and 2a-f. |
| first_indexed | 2024-12-22T03:00:52Z |
| format | Article |
| id | doaj.art-67a2e3b32378404f8fa6bf6a2dfaf736 |
| institution | Directory Open Access Journal |
| issn | 2218-0230 2412-3986 |
| language | English |
| last_indexed | 2024-12-22T03:00:52Z |
| publishDate | 2019-12-01 |
| publisher | Salahaddin University-Erbil |
| record_format | Article |
| series | Zanco Journal of Pure and Applied Sciences |
| spelling | doaj.art-67a2e3b32378404f8fa6bf6a2dfaf7362022-12-21T18:41:11ZengSalahaddin University-ErbilZanco Journal of Pure and Applied Sciences2218-02302412-39862019-12-01316617410.21271/zjpas.31.6.7Synthesis, Characterization, and Antibacterial Activity of Novel Mutual Non-Steroidal Anti-inflammatory ProdrugsBanaz mohammed hamadameen0Dana M. Hamad Ameen1Department of Pharmaceutical chemistry, College of Pharmacy, Hawler Medical University, Erbil, Kurdistan Region, IraqDepartment of Pharmaceutical chemistry, College of Pharmacy, Hawler Medical University, Erbil, Kurdistan Region, IraqNon steroidal anti-inflammatory drugs (NSAIDs) are among the most used analgesic and anti-inflammatory drugs. However inhibition of cyclooxygenase1 and acidic groups such as carboxylic groups in most NSAIDs cause gastrointestinal (GI) side effects. Therefore masking the acidic groups till it pass through the GI tract will decrease the direct GI side effects and because N-(2,6-dimethylphenyl)-acetamide 1 also has anti-inflammatory activity so the synthesized ester prodrugs might act as mutual prodrugs. Moreover, because of emerging of new strains of bacteria and resistance of bacteria to the available antibacterial agents, new antibacterial agents are needed. The NSAIDs have antibacterial activity and N-(2,6-dimethylphenyl) acetamide 1 also has antibacterial activity so binding of these molecules with each other might give more potent antibacterial agent. 2-Chloro-N-(2,6-dimethyl phenyl) acetamide 1 was utilized to synthesize ester prodrug of various NSAIDs 2a-f. The 2-Chloro-N-(2,6-dimethylphenyl)-acetamide 1 undergo substitution reaction at α position with various sodium carboxylate of NSAIDs 2a-f in DMSO. The constitution of the newly synthesized ester prodrugs of NSAIDs 3a-f had been confirmed on the basis of their IR, ¹H and ¹³C-NMR spectral data. All the synthesized ester prodrugs 3a-f were screened for their in vitro antibacterial activities against Staphylococcus aureus ATCC 25923 and Escherichia coli ATCC 25922 however, their antibacterial activity decreased compared with their starting 1 and 2a-f.https://zancojournals.su.edu.krd/index.php/JPAS/article/view/2680nsaidsantibacterialprodrugacetamide. |
| spellingShingle | Banaz mohammed hamadameen Dana M. Hamad Ameen Synthesis, Characterization, and Antibacterial Activity of Novel Mutual Non-Steroidal Anti-inflammatory Prodrugs Zanco Journal of Pure and Applied Sciences nsaids antibacterial prodrug acetamide. |
| title | Synthesis, Characterization, and Antibacterial Activity of Novel Mutual Non-Steroidal Anti-inflammatory Prodrugs |
| title_full | Synthesis, Characterization, and Antibacterial Activity of Novel Mutual Non-Steroidal Anti-inflammatory Prodrugs |
| title_fullStr | Synthesis, Characterization, and Antibacterial Activity of Novel Mutual Non-Steroidal Anti-inflammatory Prodrugs |
| title_full_unstemmed | Synthesis, Characterization, and Antibacterial Activity of Novel Mutual Non-Steroidal Anti-inflammatory Prodrugs |
| title_short | Synthesis, Characterization, and Antibacterial Activity of Novel Mutual Non-Steroidal Anti-inflammatory Prodrugs |
| title_sort | synthesis characterization and antibacterial activity of novel mutual non steroidal anti inflammatory prodrugs |
| topic | nsaids antibacterial prodrug acetamide. |
| url | https://zancojournals.su.edu.krd/index.php/JPAS/article/view/2680 |
| work_keys_str_mv | AT banazmohammedhamadameen synthesischaracterizationandantibacterialactivityofnovelmutualnonsteroidalantiinflammatoryprodrugs AT danamhamadameen synthesischaracterizationandantibacterialactivityofnovelmutualnonsteroidalantiinflammatoryprodrugs |