Chiral Alkyl Halides in Drug Discovery

Alkyl halides are a diverse class of compounds that have been used in a variety of applications, including drug discovery. Chiral alkyl halides, which have a chiral center, are of particular interest in drug discovery because they can offer a number of advantages over their achiral counterparts.

One advantage of chiral alkyl halides is that they can be more potent and selective than their achiral counterparts. This is because the chiral center can provide a point of chirality for interaction with a receptor, which can lead to improved binding affinity and selectivity.

Another advantage of chiral alkyl halides is that they can be more stable than their achiral counterparts. This is because the chiral center can provide a barrier to racemization, which is the process by which a chiral compound converts to its racemic (achiral) form.

Finally, chiral alkyl halides can be more easily manufactured than their achiral counterparts. This is because the chiral center can be introduced into the molecule using a variety of methods, including asymmetric synthesis and enzymatic resolution.

As a result of these advantages, chiral alkyl halides have been used in a number of successful drugs, including:

Halothane, an anesthetic

Clindamycin, an antibiotic

Pimecrolimus, an immunosuppressant

Sucralose, a sweetener

Chiral alkyl halides continue to be an important class of compounds in drug discovery, and they are likely to play a role in the development of new and improved drugs in the future.

References

1. "Chiral Alkyl Halides: Underexplored Motifs in Medicine." Frontiers in Pharmacology, vol. 7, 2016, doi:10.3389/fphar.2016.00279.

2. "A Unified and Desymmetric Approach to Chiral Tertiary Alkyl Halides." Journal of the American Chemical Society, vol. 144, no. 1, 2022, pp. 101–104., doi:10.1021/jacs.1c12404.