494209-39-1Relevant academic research and scientific papers
The structure-activity profile of mercaptobenzamides’ anti-HIV activity suggests that thermodynamics of metabolism is more important than binding affinity to the target
Nikolayevskiy, Herman,Robello, Marco,Scerba, Michael T.,Pasternak, Evan H.,Saha, Mrinmoy,Hartman, Tracy L.,Buchholz, Caitlin A.,Buckheit, Robert W.,Durell, Stewart R.,Appella, Daniel H.
, p. 818 - 837 (2019/06/27)
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.
Glycosylated foldamers to probe the carbohydrate-carbohydrate interaction
Simpson, Graham L.,Gordon, Andrew H.,Lindsay, David M.,Promsawan, Netnepa,Crump, Matthew P.,Mulholland, Keith,Hayter, Barry R.,Gallagher, Timothy
, p. 10638 - 10639 (2007/10/03)
The synthesis of a triglycosylated helical foldamer based on a combination of cyclopentyl- and pyrrolidinyl-based amino acids is described. This structure is stable in water, maintaining as it does a series of carbohydrate units in proximity to one another, and represents the basis of a new approach to the study of carbohydrate-carbohydrate interactions. Copyright
A novel preparation of 2-aminocyclopentanecarboxamides
Csomos, Peter,Bernath, Gabor,Fueloep, Ferenc
, p. 1077 - 1084 (2007/10/03)
Different syntheses of cis- and trans-2-aminocyclopentanecarboxamides were studied. A convenient and effective method was devised for the preparation of cis-2-aminocyclopentanecarboxamide derivatives starting from the readily available 6-tert-butoxycarbon
