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Carboranyl Analogues of Mefenamic Acid and Their Biological Evaluation. 2022

Liridona Useini, and Marija Mojić, and Markus Laube, and Peter Lönnecke, and Jonas Dahme, and Menyhárt B Sárosi, and Sanja Mijatović, and Danijela Maksimović-Ivanić, and Jens Pietzsch, and Evamarie Hey-Hawkins
Faculty of Chemistry and Mineralogy, Institute of Inorganic Chemistry, Leipzig University, Johannisallee 29, 04103 Leipzig, Germany.

Mefenamic acid represents a widely used nonsteroidal anti-inflammatory drug (NSAID) to treat the pain of postoperative surgery and heavy menstrual bleeding. Like other NSAIDs, mefenamic acid inhibits the synthesis of prostaglandins by nonselectively blocking cyclooxygenase (COX) isoforms COX-1 and COX-2. For the improved selectivity of the drug and, therefore, reduced related side effects, the carborane analogues of mefenamic acid were evaluated. The ortho-, meta-, and para-carborane derivatives were synthesized in three steps: halogenation of the respective cluster, followed by a Pd-catalyzed B-N coupling and hydrolysis of the nitrile derivatives under acidic conditions. The COX inhibitory activity and cytotoxicity for different cancer cell lines revealed that the carborane analogues have stronger antitumor potential compared to their parent organic compound.

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