Approaches for introducing high molecular diversity in scaffolds: Fast parallel synthesis of highly substituted 1H-quinolin-4-one libraries

Vladimir Kuznetsov, Sofia Gorohovsky, Amalia Levy, Simcha Meir, Vladimir Shkoulev, Naim Menashe, Moshe Greenwald, Alexander Aizikovich, Dror Ofer, Gerardo Byk, Garry Gellerman

Research output: Contribution to journalArticlepeer-review

5 Scopus citations

Abstract

We have developed a two steps strategy for the parallel synthesis of highly diversified quinolin-ones. In the first step we have combined and improved different synthetic methods for generating quinolin-4-ones bearing four different substitutions at specific positions using round bottomed flasks. The synthesis was assessed for a large number of substituted quinolin-4-ones. In the second step, the improved method was adapted to a parallel array synthesis using a 12 positions carrousel as demonstrated for the synthesis of 42-variable quinolin-4-ones. The first combinatorial library set 14{a-x} was obtained with a chemical purity of more than 95% without purification, the second library set 15{a-r}, which included two synthetic steps, needed combinatorial purification using an innovative parallel purifier. The proposed approach contributes to a more extensive diversification of molecular scaffolds in general and provides access to highly substituted quinolinones in particular.

Original languageEnglish
Pages (from-to)437-448
Number of pages12
JournalMolecular Diversity
Volume8
Issue number4
DOIs
StatePublished - 24 Nov 2004
Externally publishedYes

Keywords

  • 1H-quinolin-one
  • scaffold decoration

ASJC Scopus subject areas

  • Catalysis
  • Information Systems
  • Molecular Biology
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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