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From β‐Amino‐γ‐sultone to Unusual Bicyclic Pyridine and Pyrazine Heterocyclic Systems: Synthesis and Cytostatic and Antiviral Activities
Author(s) -
de Castro Sonia,
Familiar Olga,
Andrei Graciela,
Snoeck Robert,
Balzarini Jan,
Camarasa MaríaJosé,
Velázquez Sonsoles
Publication year - 2011
Publication title -
chemmedchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.817
H-Index - 100
eISSN - 1860-7187
pISSN - 1860-7179
DOI - 10.1002/cmdc.201000546
Subject(s) - pyrazine , bicyclic molecule , pyridine , chemistry , stereochemistry , combinatorial chemistry , human immunodeficiency virus (hiv) , medicinal chemistry , biology , virology
Herein we describe the first successful application of the β‐amino‐γ‐sultone system as an intermediate for the synthesis of hitherto virtually unknown 3 H ‐[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 3 a , 15 a , and 21 a inhibited HIV‐1‐induced cytopathicity. Compound 7 showed remarkable cytostatic activity, and can be regarded as a potential antitumor candidate for further exploration.