Synthesis of Celecoxib and Structural Analogs- A Review

Non-steroidal anti-inflammatory drugs (NSAIDs) are an important class of therapeutics, incorporate a heterocyclic core in their molecular structure and are used for the alleviation of pain and inflammation associated with several pathological conditions. NSAIDs exert anti-inflammatory effects by inhibiting cyclooxygenase enzymes (COXs) which, are useful in the synthesis of prostanoids generated from arachidonic acid. Selective COX-II inhibitors, compared to nonselective inhibitors exhibit reduced gastrointestinal, ulceration and renal side effects. In general, COX-II inhibitors incorporate a five or six-membered heterocyclic motif with built-in sulfonamide or methylsulfonate moiety. Celecoxib, a selective COX-II inhibitor drug, commercialized by Pfizer is applied in the treatment of rheumatoid arthritis, osteoarthritis, and painful menstruation related symptoms. The current review provides a discussion on the methodologies used to construct celecoxib/celebrex® and structural analogs.