Organic & Biomolecular Chemistry 2010-05-07

Reagent based DOS: a "Click, Click, Cyclize" strategy to probe chemical space.

Alan Rolfe, Gerald H Lushington, Paul R Hanson

Index: Org. Biomol. Chem. 8(9) , 2198-203, (2010)

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Abstract

The synthesis of small organic molecules as probes for discovering new therapeutic agents has been an important aspect of chemical-biology. Herein we report a reagent-based, diversity-oriented synthetic (DOS) strategy to probe chemical and biological space via a "Click, Click, Cyclize" protocol. In this DOS approach, three sulfonamide linchpins underwent cyclization protocols with a variety of reagents to yield a collection of structurally diverse S-heterocycles. In silico analysis is utilized to evaluate the diversity of the compound collection against chemical space (PC analysis), shape space (PMI) and polar surface area (PSA) calculations.