Solid-Phase Organic Chemistry Synthesis of 2β-(Heterocyclylthiomethyl)Penam Derivatives on Solid Support 英文参考文献.docVIP

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Solid-Phase Organic Chemistry Synthesis of 2β-(Heterocyclylthiomethyl)Penam Derivatives on Solid Support 英文参考文献.doc

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Solid-Phase Organic Chemistry Synthesis of 2β-(Heterocyclylthiomethyl)Penam Derivatives on Solid Support 英文参考文献

537 Molecules 2000, 5 Solid-Phase Organic Chemistry: Synthesis of 2β-(Heterocyclylthiomethyl)Penam Derivatives on Solid Support Carina M.L. Delpiccolo and Ernesto G. Mata Instituto de Química Orgánica de Síntesis (CONICET - UNR), Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario, Casilla de Correo 991, 2000 – Rosario, Argentina E-mail: emata@agatha.unr.edu.ar Abstract: The synthesis of 2β-(heterocyclylthiomethyl)penam derivatives on solid support has been developed. Compounds are obtained in good to high yields (based on loading of the original resin). The key step is the solid-phase double rearrangement of the correspond- ing penicillin sulfoxide. Introduction The impact of combinatorial chemistry of small molecules on the drug discovery process is now widely recognized by the scientific community [1]. Solid-phase organic synthesis (SPOS) is a valuable tool for the generation of structurally diverse compounds for combinatorial libraries. In our work dealing with the solid-phase synthesis of biologically interested compounds, we have developed methodologies for tethering funtionalized polystyrene resins to penicillin derivatives. Our research has also established a new, mild and efficient procedure for the removal of sensitive mole- cules from Merrifield and Wang resins, using aluminum chloride (AlCl3) [2]. Results and discussion Heterocyclic thio substituents have been identified as pharmacophores in β?lactam chemistry, par- ticularly with activity against methicillin-resistant staphylococcus aureus (MRSA) [3]. Thus, we con- sidered the solid-phase synthesis of 2β-(heterocyclylthio)methyl substituted penicillins as a rapid and efficient method for the generation of combinatorial libraries. The key step of this synthesis of the double rearrangement of sulfoxide 1 (Scheme 1). The thermal rearrangement of 1 generates the sulfenic acid which is trapped by the corresponding heterocycl