Synthesis of new aza-analogs of staurosporine, K-252a and rebeccamycin by nucleophilic opening of C2-symmetric bis-aziridines.
Stable, water-soluble aminosugar staurosporine, K-252a and rebeccamycin analogs have been prepared by nucleophilic opening of C(2)-symmetric N-activated bis-aziridines by bis-indolylmaleimides. This divergent strategy allows the synthesis of unsymmetrical substituted derivatives and provides an easy access to the piperidine and pyrrolidine analogs.
Delarue-Cochin
Sandrine
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Laboratoire de Chimie et Biochimie Pharmacologiques et Toxicologiques, UMR 8601 CNRS, Université Paris Descartes, 45 rue des Saints-Pères, 75270, Paris Cedex 06, France.
McCort-Tranchepain
Isabelle
I
D001372:Aza Compounds; D001388:Aziridines / Q000737:chemistry*; D004355:Drug Stability; D010880:Piperidines; D011759:Pyrrolidines; D012995:Solubility; D019311:Staurosporine / Q000031:analogs & derivatives* / Q000138:chemical synthesis
D001372:Aza Compounds; D001388:Aziridines; D010880:Piperidines; D011759:Pyrrolidines; C032727:piperidine; D019311:Staurosporine; C032519:pyrrolidine