Structurally rigid groups

Groups that are structurally rigid are unsaturated groups of all types and saturated ring systems (Fig. 2.1). The former includes esters and amides as well as aliphatic conjugated systems and aromatic and heteroaromatic ring systems. The binding of these rigid structures ch3 h h ch

Selegiline (MAO inhibitor)

"C CH2CH2N(C2H5)2

1-Ethoxycarbonyl-2-trimethylaminocyclopropane (acetylcholine mimic)


Procaine (local anaesthetic)


Figure 2.1 Examples of structural groups that impose a rigid shape on sections of a molecule. The shaded areas represent the rigid sections of the molecule h

to a target site can give information about the shape of that site as well as the nature of the interaction between the site and the ligand. Rigid structures may also be used to determine the conformation assumed by a ligand when it binds to its target site (see section 2.3.2). Furthermore, the fact that the structure is rigid means it may be replaced by alternative rigid structures of a similar size and shape to form analogues that may have different binding characteristics and possibly, as a result, a different activity or potency.

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