The name of these molecules borrows from a term coined by Irving Langmuir (“LANG-myoor”) to refer to any pair of compounds that have the same number of atoms and valence electrons. For 10 points each:
[10h] Give this term for molecules that structurally resemble known drugs but have been slightly engineered to improve their solubility or safety profile.
ANSWER: bioisosteres (“bio-iso-steers”) [or isosterism; or biostere or biosterism]
[10e] A common “classical” bioisostere replaces a hydrogen atom in a drug with this isotope, which is only one neutron heavier but is much more stable in the body.
ANSWER: deuterium [prompt on D]
[10m] More exciting bioisosteres have subbed out phenyl pharmacophores with this eight-carbon molecule. This compound is roughly the same size as benzene, but boasts the highest density and energy density of any hydrocarbon because of its 90-degree bonds.
ANSWER: cubane [or pentacyclooctane; prompt on C8H8]
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