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Book Recommendations


A couple of years ago, I referred to a journal article summarizing many recent examples of bioisosteres in medicinal chemistry. I’ve been meaning to mention a book that came out late last year, Bioisosteres in Medicinal Chemistry. It looks to be a compendium of all the latest information on functional group substitutions and their effects on solubility, pharmacokinetics, metabolism and the like. Worth a look if this is one of your interests – you can look over the table of contents at that Amazon link.

8 comments on “Bioisosteres”

  1. Galen says:

    Any one have an idea for a bioisostere for aryl or het-aryl trifluoromethoxy? Bonus points for added solubility.

  2. Galen says:

    ^besides halogens.

  3. mmm says:

    how about bioisosteres for isoquinoline

  4. Insilicoconsulting says:

    I frequently mine biosteres from bioactivity/bioassay data at pubchem and chembl , other than ones mentioned in literature .
    A very useful site is .

  5. chris says:


  6. Pete says:

    Understanding the conformational preferences of what you’re trying to replace usually represents a good start to bioisostere design.

  7. istvan says:

    Searching BIOSTER for “trifluoromethoxy” retrieved
    1) the obvious “trifluoromethylthio” group:
    McEvoy F J et al, J Med Chem, 11: 1248 (1968)
    Ducray P et al, Bioorg Med Chem Lett, 18: 2935 (2008)
    2) “cyclopentyloxy”:
    Lowe J A III et al, Bioorg Med Chem Lett, 20: 907 (2010)
    3) an interesting replacement is based on a benzhydryl-to-trifluoromethoxybenzyl was also found:
    Taylor S J et al, Bioorg Med Chem Lett, 19: 5864 (2009)
    Good luck 😉

  8. istvan says:

    SORRY for multiple uploads…
    For mmm on isoquinolines, here are some examples from BIOSTER:
    furopyridine, phenylpyridine, indazole, isoquinolinone, pyridopyridazine, N,N-dimethylaniline, pyrazolotriazine, dihydroisoquinoline, iminochromene, chromanone, quinazoline, phthalazine, cinnamonitrile, benzimidazole, o-dichlorobenzene, benzamide, naphthyridine, phenyl ketone, and vinylpyridine (vinyl replaceing the ‘benzene’ ring system).

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