- Sulfoximines from a Medicinal Chemist's Perspective: Physicochemical and in vitro Parameters Relevant for Drug Discovery
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Sulfoximines, sulfondiimides and sulfonimidamides are fascinating but not yet fully explored variants of the common sulfone or sulfonamide motif. In this study, we report the physicochemical and in vitro properties of sulfoximines and compare them with related analogs and isosteres. Furthermore, we present a matched molecular pair analysis of compounds from drug discovery projects within Boehringer Ingelheim. We demonstrate that the sulfoximine moiety is a chemically stable, comparatively polar and weakly basic functional group, often leading to favorable aqueous solubility, permeability and metabolic stability. Moreover, their additional vectors at nitrogen enable simple chemical modifications and thus facilitate exploration and fine-tuning of the molecular properties. We conclude that sulfoximines and their congeners do not exhibit any intrinsic flaw but significantly enrich the toolbox of medicinal chemists.
- Frings, Marcus,Bolm, Carsten,Blum, Andreas,Gnamm, Christian
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supporting information
p. 225 - 245
(2016/11/19)
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- A ONE-STEP TRANSFORMATION OF AROMATIC ALDEHYDES TO NITRILES, USING S,S-DIMETHYL SULFURDIIMIDE AS IMINATING AGENT. ISOLATION OF DITHIATETRAZOCINES AS REACTION INTERMEDIATES.
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S;S-Dimethylsulfurdiimide is explored as a novel and effective reagent for the direct synthesis of aromatic nitriles from aldehydes.A novel eight-membered heterocycle is isolated as a reaction intermediate and a mechanism for this reaction is discussed.
- Georg, Gunda I.,Pfeifer, Sarah A.
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p. 2739 - 2742
(2007/10/02)
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