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]
<Chemistry>
Summary
| 2023 ACF Nationals | 04/22/2023 | Y | 20 | 12.50 | 90% | 35% | 0% |
Data
| Claremont A | Northwestern A | 0 | 10 | 0 | 10 |
| Cornell A | Imperial A | 0 | 10 | 0 | 10 |
| WUSTL A | Yale B | 0 | 10 | 10 | 20 |
| Iowa State A | Chicago B | 0 | 10 | 0 | 10 |
| Chicago C | MIT A | 0 | 10 | 10 | 20 |
| Columbia B | Purdue A | 0 | 10 | 0 | 10 |
| Florida A | South Carolina A | 0 | 0 | 0 | 0 |
| Georgia Tech B | NYU A | 0 | 0 | 10 | 10 |
| Johns Hopkins A | Virginia A | 0 | 10 | 0 | 10 |
| Chicago A | Minnesota A | 0 | 10 | 10 | 20 |
| Ohio State A | Texas A | 0 | 10 | 0 | 10 |
| Florida B | Penn State A | 0 | 10 | 0 | 10 |
| Harvard A | Rutgers A | 0 | 10 | 10 | 20 |
| WUSTL B | Rutgers B | 0 | 10 | 10 | 20 |
| Houston A | Vanderbilt A | 0 | 10 | 0 | 10 |
| Cornell B | Stanford A | 0 | 10 | 0 | 10 |
| Georgia Tech A | Illinois A | 0 | 10 | 10 | 20 |
| Michigan A | Duke A | 0 | 10 | 0 | 10 |
| Indiana A | Toronto A | 0 | 10 | 0 | 10 |
| McGill A | UC Berkeley B | 0 | 10 | 0 | 10 |