Abstract
Bioisosteric replacement is a standard technique that is used in medicinal chemistry to design analogs of bioactive molecules with similar biological activity and with additional improved characteristics. Successful application of this technique relies on a good knowledge of physicochemical properties of common organic substituents and an efficient way to navigate their space. In this study the properties of the most common substituents present in bioactive molecules are analysed and a freely-available web tool https://bit.ly/craigplot that allows visualization, analysis and selection of bioisosteric substituents is presented.
Highlights
A bioisosteric replacement may be defined as the replacement of a part of a bioactive molecule with a substructure that is similar in size and exhibits similar physicochemical properties
Bioisosteric replacements are used in situations where the optimization is intended to improve the synthetic accessibility of the molecule
In our earlier study we find out that only 63 of the 100 most common substituents have been characterized experimentally [10]
Summary
A bioisosteric replacement may be defined as the replacement of a part of a bioactive molecule with a substructure that is similar in size and exhibits similar physicochemical properties. Various computational methods can provide useful help in navigating the space of substituents and identifying the groups with similar physicochemical properties. Many other approaches to navigate the substituent property space to help medicinal chemists have been explored, see [5] for a review.
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