Use of the transannular Diels–Alder (TADA) reaction to probe biological receptors: Rational design and synthesis of tricyclic TADA adducts capable of rigidly holding pharmacophore parts (original) (raw)

Canadian Journal of Chemistry, 2002

Abstract

Transannular Diels–Alder (TADA) adducts constitute a collection of rigid structures, whose conformational diversity is rich. It is possible to design such specifically functionalized molecules capable of binding to known biological targets by molecular modelling MCSS–HOOK (multiple copy simultaneous search). Here we show that such carefully designed compounds can be easily built from small synthons. TADA adducts are very interesting due to their huge conformational diversity, their rigidity (biological interest), and their ease of synthesis (chemical interest).Key words: tricycles, synthesis, transannular Diels–Alder, macrocyclization, conformation, diversity.

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