Applications of amide isosteres in medicinal chemistry

Shaoyi Sun; Qi Jia; Zaihui Zhang

doi:10.1016/j.bmcl.2019.07.033

Applications of amide isosteres in medicinal chemistry

Bioorg Med Chem Lett. 2019 Sep 15;29(18):2535-2550. doi: 10.1016/j.bmcl.2019.07.033. Epub 2019 Jul 22.

Authors

Shaoyi Sun¹, Qi Jia², Zaihui Zhang³

Affiliations

¹ Xenon Pharmaceuticals Inc., 200-3650 Gilmore Way, Burnaby, BC V5G 4W8, Canada. Electronic address: [email protected].
² Xenon Pharmaceuticals Inc., 200-3650 Gilmore Way, Burnaby, BC V5G 4W8, Canada.
³ Signalchem Lifesciences Corp., 110-13210, Vanier Place, Richmond, BC V6V 2J2, Canada.

PMID: 31377035
DOI: 10.1016/j.bmcl.2019.07.033

Abstract

Isosteric replacement of amide groups is a classic practice in medicinal chemistry. This digest highlights the applications of most commonly employed amide isosteres in drug design aiming at improving potency and selectivity, optimizing physicochemical and pharmacokinetic properties, eliminating or modifying toxicophores, as well as providing novel intellectual property of lead compounds.

Keywords: 3-Aminooxetane; Amide isostere; Boronic acid; Fluoroalkene; Heterocycle; Transition-state mimic; Trifluoroethylamine.

Publication types

Review

MeSH terms

Amides / chemical synthesis*
Amides / chemistry
Amides / pharmacokinetics
Chemistry, Pharmaceutical*
Drug Design*
Molecular Structure

Substances

Amides