Solid-phase Parallel Synthesis of a Novel N-[Alkylsulfonamido-spiro(2H-1-benzopyran-2,4-piperidine)-6-yl] substituted Amide and Amine Drug-like Libraries

Abstract

Center for Drug Discovery Platform Technology, Korea Research Institute of Chemical Technology, Daejeon 305-600, Korea Received November 1, 2011, Accepted November 11, 2011We report the solid-phase library construction of 222 number of a novel N-[alkyl sulfonamido-spiro(2H-1-benzopyran-2,4-piperidine)-6-yl] substituted amide 1A and amine 1B derivatives. The polymer-bound N-[alkylsulfonamido-spiro(2H-1-benzopyran-2,4-piperidine)-6-yl] substituted amide 9 and amine 10 derivativeswere obtained by first diversity generation with various acid chlorides and alkyl halides. Further reactions onthe resins 9 and 10 with substituted sulfonyl chlorides produced the desired N-[alkylsulfonamido-spiro(2H-1-benzopyran-2,4-piperidine)-6-yl] substituted amide 1A and amine 1B analogues.Key Words : Spiro(2H-1-benzopyran-2,4-piperidine)-6-yl derivatives, Solid-phase parallel synthesis, Drug-like benzopyran core skeleton IntroductionHeterocyclic compounds provide scaffolds on whichpharmacophores can be arranged to yield potent andselective drugs, and a variety of heterocycles have beensynthesized on solid support.