Potent β-Lactam Inhibitors of Human Cytomegalovirus Protease
- 1 October 1998
- journal article
- Published by SAGE Publications in Antiviral Chemistry and Chemotherapy
- Vol. 9 (5), 379-387
- https://doi.org/10.1177/095632029800900502
Abstract
A series of novel monobactam inhibitors of human cytomegalovirus (HCMV) protease has been described that possess a heterocyclic thiomethyl side chain at C-4. Changes to the heterocycle did not significantly change the inhibitory activity of these compounds in an enzymatic assay, although improvements in solubility and cell culture activity were noted. A number of permutations between C-4 substitutions and N-1 derivatives led to the identification of several β-lactams with antiviral activity in a plaque reduction assay. N-methyl thiotetrazole-containing compounds were found to be the most potent inhibitors in the enzymatic assay.Keywords
This publication has 22 references indexed in Scilit:
- Design and synthesis of monocyclic β-lactams as mechanism-based inhibitors of human cytomegalovirus proteaseBioorganic & Medicinal Chemistry Letters, 1998
- Peptidomimetic Inhibitors of the Human Cytomegalovirus ProteaseJournal of Medicinal Chemistry, 1997
- Unique fold and active site in cytomegalovirus proteaseNature, 1996
- A new serine-protease fold revealed by the crystal structure of human cytomegalovirus proteaseNature, 1996
- Asymmetric Deprotonation by BuLi/(−)-Sparteine: Convenient and Highly Enantioselective Syntheses of (S)-2-Aryl-Boc-PyrrolidinesJournal of the American Chemical Society, 1996
- Orally Active .beta.-Lactam Inhibitors of Human Leukocyte Elastase. 3. Stereospecific Synthesis and Structure-Activity Relationships for 3,3-Dialkylazetidin-2-onesJournal of Medicinal Chemistry, 1995
- In vitro Proteolytic Activity and Active‐Site Identification of the Human Cytomegalovirus ProteaseEuropean Journal of Biochemistry, 1994
- Intramolecular Cyclizations of .alpha.-Lithioamine Synthetic Equivalents: Convenient Syntheses of 3-, 5-, and 6-Membered-Ring Heterocyclic Nitrogen Compounds and Elaborations of 3-Membered Ring SystemsThe Journal of Organic Chemistry, 1994
- TheMitsunobu ReactionPublished by Wiley ,1992
- Development and use of quantum mechanical molecular models. 76. AM1: a new general purpose quantum mechanical molecular modelJournal of the American Chemical Society, 1985