ArticleEuropean journal of medicinal chemistry2019
The structure-activity profile of mercaptobenzamides' anti-HIV activity suggests that thermodynamics of metabolism is more important than binding affinity to the target.
Article in European journal of medicinal chemistry, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.
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Who cites it
4 citing papers in PubMed.
- Sulfanylbenzamides with Unique Side Chains to Improve Metabolic Stability, Pharmacokinetics, and Anti-HIV Activity.Journal of medicinal chemistry · 2025Article
- Prodrug Strategy Extends the Use of Anti-HIV Sulfanylbenzamides for ApplicationACS pharmacology & translational science · 2024Article
- On the application of 3d metals for C-H activation toward bioactive compounds: The key step for the synthesis of silver bullets.Beilstein journal of organic chemistry · 2021Review
- Asymmetric Disulfanylbenzamides as Irreversible and Selective Inhibitors of Staphylococcus aureus Sortase A.ChemMedChem · 2020Article
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Authors and funding
10 authors.
Funding
Abstract
Mercaptobenzamide thioesters and thioethers are chemically simple HIV-1 maturation inhibitors with a unique mechanism of action, low toxicity, and a high barrier to viral resistance. A structure-activity relationship (SAR) profile based on 39 mercaptobenzamide prodrug analogs exposed divergent activity/toxicity roles for the internal and terminal amides. To probe the relationship between antiviral activity and toxicity, we generated an improved computational model for the binding of mercaptobenzamide thioesters (SAMTs) to the HIV-1 NCp7 C-terminal zinc finger, revealing the presence of a second low-energy binding orientation, hitherto undisclosed. Finally, using NMR-derived thiol-thioester exchange equilibrium constants, we propose that thermodynamics plays a role in determining the antiviral activity observed in the SAR profile.
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