85535-56-4Relevant 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.
Direct preparation of primary amides by reaction of carboxylic acids and ammonia in alcohols using DMT-MM
Mizuhara, Tsukasa,Hioki, Kazuhito,Yamada, Megumi,Sasaki, Hideaki,Morisaki, Daiki,Kunishima, Munetaka
body text, p. 1191 - 1192 (2009/12/01)
A simple and mild method for the direct conversion of carboxylic acids to primary amides has been developed by using 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)- 4-methylmorpholim'um chloride (DMT-MM). The reaction proceeds by adding DMT-MM to a mixture of carboxylic acids and an ammonia source in methanol, 2-propanol, or THF without any additives. The present method is quite practical in that aqueous ammonia or ammonium chloride/triethylarnine can be used as an ammonia source. Methanol or 2-propanol is an ideal polar solvent because it is inexpensive, can be removed by rotary evaporator, and solubilizes many kinds of polar or nonpolar compounds.
A Convenient and General Method for the Preparation of tert-Butoxycarbonylaminoalkanenitriles and Their Conversion to Mono-tert-butoxycarbonylalkanediamines
Houssin, Raymond,Bernier, Jean-Luc,Henichart, Jean-Pierre
, p. 259 - 261 (2007/10/02)
A new method is described for the synthesis of tert-butoxycarbonylaminoalkanenitriles 3 by dehydration of the corresponding carboxamides 2 (prepared in two steps from aminoalkanoic acids) in the presence of trifluoroacetic anhydride and triethylamine.N-Boc-aminoalkanenitriles 3 are easily converted to mono-N-Boc-alkanediamines 4 under mild conditions avoiding the cleavage of the N-protective group.The monoprotected alkanediamines 4 are useful tools in affinity chromatography.
