Arylidene oxindoles represent a novel class of small molecule cell death inhibitors. Conceptually, methods for the preparation of arylidene oxindoles are described by routes involving, either: a) N-alkylation of 5-substituted isatins followed by Wolff-Kishner reduction to the corresponding oxindoles and final Knoevenagel condensation with aryl aldehydes, or; b) Wolff-Kishner reduction of the isatins followed by condensation and culminating in the N-alkylation of the aldol products. In order to facilitate the expedited synthesis of a series of 5-halo analogues for screening purposes, processes have been developed to enable the N-alkylation step to be carried wherein the solid base (KF-Al2O3) can be filtered and the product precipitates from the filtrate, or a soluble base (DBU) is employed wherein crystallization occurs directly in the reaction medium. The extension of this methodology to molecules capable of serving as potential imaging agents for apoptosis will be described.

Expedited synthesis of arylidene oxindoles with three points of diversity

245th National Meeting (2013)

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