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Bioisosteric Replacement and Scaffold Hopping in Lead Generation and Optimization

Langdon, Sarah, Ertl, Peter and Brown, Nathan (2010) Bioisosteric Replacement and Scaffold Hopping in Lead Generation and Optimization. Molecular Informatics, 29 (5). pp. 366-385.


Bioisosteric replacement and scaffold hopping are twin methods used in drug discovery to improve the synthetic accessibility, potency and drug like properties of a compound and to move into novel chemical space. Bioisosteric replacement involves swapping functional groups of a molecule with other functional groups that have similar biological properties. Scaffold hopping is the replacement of the core framework of a molecule with another scaffold that will improve the properties of the molecule or to find similar potent compounds that exist in novel chemical space.
This review outlines the key concepts, importance and challenges of both methods using examples and comparisons of techniques available for finding bioisosteric replacements and scaffold hops. There are many methods available for bioisosteric replacement and scaffold hopping, all with their own advantages and disadvantages. Drug discovery projects would benefit from a combination of these methods to retrieve diverse and complimentary results. Continuing progress in these fields will allow further validation of both methods as well as the accumulation of knowledge on bioisosteres and possible scaffold replacements.

Item Type: Article
Keywords: bioisosteric replacement, scaffold hopping, cheminformatics
Date Deposited: 13 Oct 2015 13:16
Last Modified: 13 Oct 2015 13:16


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