1097641-68-3Relevant academic research and scientific papers
From β-Amino-γ-sultone to Unusual Bicyclic Pyridine and Pyrazine Heterocyclic Systems: Synthesis and Cytostatic and Antiviral Activities
deCastro, Sonia,Familiar, Olga,Andrei, Graciela,Snoeck, Robert,Balzarini, Jan,Camarasa, Maria-Jose,Velazquez, Sonsoles
scheme or table, p. 686 - 697 (2012/01/05)
Herein we describe the first successful application of the β-amino-γ-sultone system as an intermediate for the synthesis of hitherto virtually unknown 3H-[1,2]-oxathiole [4,3-b]pyridine and pyrazine 1,1-dioxide bicyclic heterocyclic systems. All novel compounds were evaluated for their antiviral and cytostatic activities. Compounds 3a, 15a, and 21a inhibited HIV-1-induced cytopathicity. Compound 7 showed remarkable cytostatic activity, and can be regarded as a potential antitumor candidate for further exploration.
Reactivity of the 4-amino-5H-1,2-oxathiole-2,2-dioxide heterocyclic system: A combined experimental and theoretical study
De Castro, Sonia,Teresa Peromingo,Lozano, Angel E.,Camarasa, Maria-Jose,Velazquez, Sonsoles
experimental part, p. 9620 - 9632 (2009/10/01)
The reactivity of the 4-amino-5H-1,2-oxathiole-2,2-dioxide (or β-amino-γ-sultone) heterocyclic system has scarcely been studied. Here we describe the reactivity of this system towards electrophiles and amines on readily available model substrates differently substituted at the C-5 position. A variety of C-electrophiles, carbonyl electrophiles (such as acyl chlorides, isocyanates, or aldehydes) and halogen or nitrogen electrophiles have been explored. Both the C-3 and 4-amino positions of the β-amino-γ- sultone system are able to undergo electrophilic reactions, and the reaction products depend on the electrophile used and on the reaction conditions. On the other hand, nucleophilic attack of amines occurs at the C-4 position of the β-amino-γ-sultone system only in spiranic substrates bearing alicyclic substituents at the C-5 position. A comparative computational study between spiranic and non-spiranic substrates suggests that conformational changes, undergone on intermediate compounds, account for the observed reactivity differences. Moreover, these conformational changes seem to bring about an increase of electron density on the N-4 and C-3 atoms of the enaminic system, and a possible enhancement in the reactivity of spiranic substrates towards electrophiles in the presence of amines. Experimental data consistent with this predicted enhanced reactivity is also presented.
