Question

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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Data

TeamOpponentPart 1Part 2Part 3Total
Chicago AMinnesota A0101020
Chicago CMIT A0101020
Claremont ANorthwestern A010010
Columbia BPurdue A010010
Cornell AImperial A010010
Cornell BStanford A010010
Florida ASouth Carolina A0000
Florida BPenn State A010010
Georgia Tech AIllinois A0101020
Georgia Tech BNYU A001010
Harvard ARutgers A0101020
Houston AVanderbilt A010010
Indiana AToronto A010010
Iowa State AChicago B010010
Johns Hopkins AVirginia A010010
McGill AUC Berkeley B010010
Michigan ADuke A010010
Ohio State ATexas A010010
WUSTL AYale B0101020
WUSTL BRutgers B0101020