Abstract
The hydrochloride salt of ɑ-aminocyclobutanone protected as its dimethyl acetal 2,2-dimethoxycyclobutan-1-aminium chloride (3) has been prepared as a modular synthon for convenient access to cyclobutanone-containing lead inhibitors of hydrolase enzymes including serine proteases and metalloproteases. Protected ɑ-aminocyclobutanone 3 was converted to representative amide and sulfonamide-functionalized 2-aminocyclobutanone derivatives. Reaction of the amino acetal 3 with phenyl isothiocyanate afforded the bicyclic urea 1-hydroxyl-2,4-diazabicyclo[3.2.0]heptane-3-thione (9) as confirmed by a single crystal X-ray structure.
Original language | American English |
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Journal | Chemistry: Faculty Publications and Other Works |
Volume | 61 |
Issue number | 12 |
DOIs | |
State | Published - Mar 19 2020 |
Keywords
- Cyclobutanone
- Enzyme inhibitor
- Transition state mimetic
- Strained ring
Disciplines
- Biochemistry
- Chemistry