A solid phase library synthesis of hydroxyindoline-derived tricyclic derivatives by mitsunobu approach

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DOIResolve DOI: http://doi.org/10.1021/cc0340067
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TypeArticle
Journal titleJournal of Combinatorial Chemistry
ISSN1520-4766
Volume6
Issue1
Pages6572; # of pages: 8
AbstractHydroxyindoline-derived scaffold, 9, was synthesized with the goal of generating a library of indolinebased natural product-like tricyclic derivatives to be utilized as small-molecule chemical probes. The tricyclic ring was obtained by a Mitsunobu reaction of the N-nosyl amino acid conjugate with the primary hydroxyl group. The solid-phase synthesis was achieved by immobilizing scaffold 9 onto the solid support giving a compound, 15. This was then subjected to a series of reactions on solid phase, including the Mitsunobu reaction, leading to the desired indoline-derived tricyclic derivative. The final product has two diversity sites: (i) amino acid as the first diversity and (ii) amidation of the secondary amine for the second diversity. These two diversity sites were utilized in the library generation by IRORI split-and-mix approach.
Publication date
LanguageEnglish
AffiliationNational Research Council Canada; NRC Steacie Institute for Molecular Sciences
Peer reviewedNo
Identifier18517171
NPARC number12340896
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Record identifierbda8ca9f-9ca7-44e2-a067-ddfb2d8896d8
Record created2009-09-11
Record modified2016-05-09
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