Solution Phase Synthesis of a 3,5,7-Substituted Indolin-2-one Library as Potential CDK2 Inhibitor Isosteres

Tymoshenko, Dmytro O.; Gregg, Brian T.; Hirsch, Matthew J.; Butcher, Jennifer

doi:10.2174/157018008783406633

Cited by 5 publications

(1 citation statement)

References 21 publications

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“…These crude ester products were not purified, but were directly saponified with lithium hydroxide to the carboxylic acids 6{1-4} and 7{1-4}. Based on our previous experience [26] the best synthetic strategy for the preparation of amides in a parallel synthetic protocol is to prepare activated p-nitrophenyl (PNP) esters from the carboxylic acids. The advantages of PNP esters for carboxylate activation in parallel synthesis are many.…”

Section: Synthesis Of Scaffolds and Library Preparationmentioning

confidence: 99%

Design and Synthesis of 3-Arylisoxazoline-5-Carboxamide and 3-Arylisoxazoline-5-Acetamide Libraries as Potential Factor Xa Inhibitors

Quinn¹,

Gregg²,

Kitchen³

et al. 2012

LDDD

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Two synthetic libraries based on a core isoxazoline motif have been designed and prepared specifically to probe the S1 and S4 binding pockets of the Factor Xa enzyme active sites. A highly efficient parallel solution phase synthetic method resulted in the synthesis of 3-arylisoxazoline-5-carboxamides and 3-arylisoxazoline-5-acetamides libraries yielding 192 compounds in total. Highlights of this work include preparation of the isoxazoline cores via a [3+2] cycloaddition between oximes with acrylates or vinyl acetates and the use of activated p-nitrophenyl esters for ease of amide formation and reaction purification.

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Section: Synthesis Of Scaffolds and Library Preparationmentioning

confidence: 99%