10.1016/S0040-4039(02)01756-2
The research focuses on the facile synthesis of a selectively protected triazamacrocycle, which is of synthetic interest due to its unique binding properties with metal ions and potential applications in biomedical fields such as magnetic resonance imaging and radioimmunotherapy. The study reports a method for the regioselective N-functionalization of azamacrocycles, which is scarce in the literature. The synthesis involves the selective homologation of 1,7-diaminoheptane with the novel reagent N-(2-nitrobenzenesulfonyl)aziridine, followed by a series of reactions to afford a selectively protected 14-membered triazamacrocyclic ring. Key chemicals used in the process include N-(2-nitrobenzenesulfonyl)aziridine, N-tert-butoxycarbonyl anhydride, diethylphosphoryl chloride (DEPCl), trifluoroacetic acid (TFA), bromoacetyl bromide, and potassium carbonate (K2CO3). The conclusion of the research is the development of a method for the synthesis of selectively protected triazamacrocycles, allowing for functionalization at any ring nitrogen atom, which is a significant advancement for the synthesis of larger or smaller sized azamacrocyclic rings.
10.1021/jm00149a028
The research aimed to isolate, elucidate the structures of, and characterize the interactions of four isomers of N-(bromoacetyl)-N'-[3-(o-allylphenoxy)-2-hydroxypropyl]-1,8-diamino-p-menthane (BAAM) with β-adrenoceptors. The purpose was to understand their activity as alkylating β-blockers and their potential use in affinity labeling of β-adrenoceptors, which is a technique valuable for biochemical and physiological studies of these proteins. The study concluded that the isomer with the aromatic group on carbon 1 of p-menthane and with the 2 configuration (2-1) had the highest affinity for β-adrenoceptors in rat heart and lungs and acted as a ligand that binds irreversibly at the drug binding site of the receptor. Other isomers also showed affinity for the receptors, though with varying degrees of effectiveness and impact on receptor affinity. Key chemicals used in the process included 1,8-diamino-p-menthane, o-allylphenyl glycidyl ether, bromoacetyl bromide, and various solvents and reagents for the synthesis, purification, and testing of the isomers.
10.1016/j.bmcl.2013.02.042
The research focuses on the identification and optimization of benzofurano[3,2-d]pyrimidin-2-ones as a new series of HIV-1 nucleotide-competing reverse transcriptase inhibitors (NcRTIs). The study began with the screening of a compound collection, leading to the identification of several benzofuranopyrimidone hits. Through iterative modifications at positions N1, C4, C7, and C8 on the benzofuranopyrimidone scaffold, the researchers achieved significant improvements in antiviral potency, optimizing the compounds from low micromolar enzymatic activity to low nanomolar antiviral potency. Key chemicals that played a role in this research include the initial benzofuranopyrimidone hits (e.g., inhibitors 1, 2, and 3), various analogues with different substituents, and the optimized compound 30, which demonstrated promising in vitro properties and maintained potency against drug-resistant HIV-1 variants. The synthesis of these compounds involved various chemical reactions and reagents, such as ethyl chloroformate, NaH, bromoacetyl bromide, and boronic ester 40, as outlined in Scheme 1.
C
