Groups with similar polar effects functional equivalents

Groups with similar polar effects functional equivalents 

FIGURE 15.18 Oxazolidinone bioisosteres synthesized as antibacterial agents. 

CHAPTER 15 Molecular Variations Based on Isosteric Replacements 

For the carboxylic function of active compounds, three different classes of bioisosters can be distinguished (a) the direct derivatives (Table 15.11) (b) the planar acidic heterocycles (Table 15.12) and (c) the non-planar sulfur- or phosphorus-derived acidic functions (Table 15.5). 

Direct derivatives of carboxyhc acids are different functional groups which maintain an acidic proton and a hydrogen bond acceptor (the carbonyl) in order to have similar specific interactions with the receptor. Among the most common direct derivatives can be listed the hydroxamic acids (R—CO— NH—OH), the acylcyanamides (R—CO— NH—CN) and the acylsulfonamides (R—CO—NH- 02—R ) (Table 15.11). 

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E. Groups with similar polar effects functional equivalents... 

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