Synthesis and Preliminary Pharmacological Study of Sulfonamide Conjugates with Ibuprofen and Indomethacin as New Anti-Inflammatory Agents
4-aminobenzenesulfonamide conjugates of ibuprofen (compound 10) and indomethacin (compound 11) have been designed and synthesized by the reaction of sulfanilamide (compound 7) with 2-(4-isobutylphenyl) propanoic acid (ibuprofen) and 2-(1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)acetic acid...
| Main Authors: | , , |
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| Format: | Article |
| Language: | English |
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College of Pharmacy University of Baghdad
2017-03-01
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| Series: | Iraqi Journal of Pharmaceutical Sciences |
| Online Access: | https://bijps.uobaghdad.edu.iq/index.php/bijps/article/view/252 |
| _version_ | 1819227686799671296 |
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| author | Bader S. Salem Monther F. Mahdi Mohammed H. Mohammed |
| author_facet | Bader S. Salem Monther F. Mahdi Mohammed H. Mohammed |
| author_sort | Bader S. Salem |
| collection | DOAJ |
| description | 4-aminobenzenesulfonamide conjugates of ibuprofen (compound 10) and indomethacin (compound 11) have been designed and synthesized by the reaction of sulfanilamide (compound 7) with 2-(4-isobutylphenyl) propanoic acid (ibuprofen) and 2-(1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)acetic acid (indomethacin) for the evaluation as potential anti-inflammatory agents with expected selectivity against COX-2 enzyme. In vivo acute anti-inflammatory activity of the synthesized final compounds (10 and 11) was evaluated in rats using egg-white induced edema model of inflammation in a dose equivalent to (10mg/Kg) of ibuprofen and (2mg/kg) of indomethacin. The tested compounds produced significant reduction of the rat paw edema with respect to the effect of propylene glycol 50% v/v (control group). Moreover, compound (10) exhibited comparable anti-inflammatory activity to diclofenac (3mg/Kg) (reference group) while compound (11) exhibited less anti-inflammatory activity than diclofenac. The result of this study indicate that the incorporation of the 4-aminobenzenesulfonamide pharmacophore into ibuprofen and indomethacin maintained their anti-inflammatory activity & may increase their selectivity toward COX-2 enzyme which can be confirmed in future by assessing COX-2:COX-1 inhibitory ratio.
Key words: Cyclooxygenase; Anti-inflammatory activity; Ibuprofen; indomethacin; NSAIDs. |
| first_indexed | 2024-12-23T10:45:20Z |
| format | Article |
| id | doaj.art-8059d6ff49e34d9fb2ebee89cd64958b |
| institution | Directory Open Access Journal |
| issn | 2521-3512 1683-3597 |
| language | English |
| last_indexed | 2024-12-23T10:45:20Z |
| publishDate | 2017-03-01 |
| publisher | College of Pharmacy University of Baghdad |
| record_format | Article |
| series | Iraqi Journal of Pharmaceutical Sciences |
| spelling | doaj.art-8059d6ff49e34d9fb2ebee89cd64958b2022-12-21T17:50:02ZengCollege of Pharmacy University of BaghdadIraqi Journal of Pharmaceutical Sciences2521-35121683-35972017-03-01182Synthesis and Preliminary Pharmacological Study of Sulfonamide Conjugates with Ibuprofen and Indomethacin as New Anti-Inflammatory AgentsBader S. SalemMonther F. MahdiMohammed H. Mohammed4-aminobenzenesulfonamide conjugates of ibuprofen (compound 10) and indomethacin (compound 11) have been designed and synthesized by the reaction of sulfanilamide (compound 7) with 2-(4-isobutylphenyl) propanoic acid (ibuprofen) and 2-(1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)acetic acid (indomethacin) for the evaluation as potential anti-inflammatory agents with expected selectivity against COX-2 enzyme. In vivo acute anti-inflammatory activity of the synthesized final compounds (10 and 11) was evaluated in rats using egg-white induced edema model of inflammation in a dose equivalent to (10mg/Kg) of ibuprofen and (2mg/kg) of indomethacin. The tested compounds produced significant reduction of the rat paw edema with respect to the effect of propylene glycol 50% v/v (control group). Moreover, compound (10) exhibited comparable anti-inflammatory activity to diclofenac (3mg/Kg) (reference group) while compound (11) exhibited less anti-inflammatory activity than diclofenac. The result of this study indicate that the incorporation of the 4-aminobenzenesulfonamide pharmacophore into ibuprofen and indomethacin maintained their anti-inflammatory activity & may increase their selectivity toward COX-2 enzyme which can be confirmed in future by assessing COX-2:COX-1 inhibitory ratio. Key words: Cyclooxygenase; Anti-inflammatory activity; Ibuprofen; indomethacin; NSAIDs.https://bijps.uobaghdad.edu.iq/index.php/bijps/article/view/252 |
| spellingShingle | Bader S. Salem Monther F. Mahdi Mohammed H. Mohammed Synthesis and Preliminary Pharmacological Study of Sulfonamide Conjugates with Ibuprofen and Indomethacin as New Anti-Inflammatory Agents Iraqi Journal of Pharmaceutical Sciences |
| title | Synthesis and Preliminary Pharmacological Study of Sulfonamide Conjugates with Ibuprofen and Indomethacin as New Anti-Inflammatory Agents |
| title_full | Synthesis and Preliminary Pharmacological Study of Sulfonamide Conjugates with Ibuprofen and Indomethacin as New Anti-Inflammatory Agents |
| title_fullStr | Synthesis and Preliminary Pharmacological Study of Sulfonamide Conjugates with Ibuprofen and Indomethacin as New Anti-Inflammatory Agents |
| title_full_unstemmed | Synthesis and Preliminary Pharmacological Study of Sulfonamide Conjugates with Ibuprofen and Indomethacin as New Anti-Inflammatory Agents |
| title_short | Synthesis and Preliminary Pharmacological Study of Sulfonamide Conjugates with Ibuprofen and Indomethacin as New Anti-Inflammatory Agents |
| title_sort | synthesis and preliminary pharmacological study of sulfonamide conjugates with ibuprofen and indomethacin as new anti inflammatory agents |
| url | https://bijps.uobaghdad.edu.iq/index.php/bijps/article/view/252 |
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