Total synthesis of cis and trans-hydroxyglimepiride: active metabolite of glimepiride

Palladium‐Catalyzed Carbonylative Synthesis of 1,5‐Dihydro‐2H‐pyrrol‐2‐ones from Propargyl Amines and Benzyl Chlorides

“…1,5‐Dihydro‐2 H ‐pyrrol‐2‐ones are recognized as a class of important moieties frequently found in numerous natural products and pharmaceuticals with biological activities such as anti‐diabetic (Ypaoamide B [1] and Glimepirid [2] ), anti‐tumor (Isomalyngamide A [3] ), anti‐biotic (Althiomycin [4a] ), and immunosuppressive property (Microcolin A [4b] ). In order to establish these useful skeletons, many synthetic methods have been realized [5] .…”

Acyclic and Cyclic Ureas (Update 2013)

“…The first involves reaction of a sulfonyl isocyanate with an amine and the second utilizes reaction of a sulfonamide with an isocyanate. The first approach has been used for the synthesis of a series of N-aryl-N¢-(arylsulfonyl)ureas as potential cytotoxic and antimicrobial agents, [359] and the second for the synthesis of active metabolites of glimepiride, an antidiabetic drug, [360] and fluorinated (alkylsulfonyl)ureas. [361] Reactions with sulfonamides are usually carried out in the presence of base to deprotonate the sulfonyl NH group thereby increasing its nucleophilicity, or by using deprotonated sulfonamides directly.…”

Synthesis of Dihydro‐2‐oxopyrrole (DPO) Building Blocks Catalyzed by Potassium Carbonate

“…Dihydro‐2‐oxopyrrole (DPO) moiety is a common element within many biologically active natural products and pharmacologically important compounds such as Oteromycin , an HIV integrase inhibitor and an antagonist of endothelin receptor; Pyrrocidine , a potential antibiotic; Ypaoamide , a feeding deterrent; and Glimepiride , an antidiabetes drug (Figure ). Moreover, many DPO's derivatives themselves also exhibited useful bioactive characters such as antimalarial, pesticidal, herbicidal, etc.…”