Synthesis and antimycobacterial activity of N-(2-aminopurin-6-yl) and N-(purin-6-yl) amino acids and dipeptides.
Synthetic routes to novel N-(purin-6-yl)- and N-(2-aminopurin-6-yl) conjugates with amino acids and glycine-containing dipeptides were developed. In vitro testing of 42 new and known compounds made it possible to reveal a series of N-(purin-6-yl)- and N-(2-aminopurin-6-yl) conjugates exhibiting significant antimycobacterial activity against Mycobacterium tuberculosis H37Rv, Mycobacterium avium, Mycobacterium terrae, and multidrug-resistant M. tuberculosis strain isolated from tuberculosis patients in the Ural region (Russia). N-(2-Aminopurin-6-yl)- and N-(purin-6-yl)-glycyl-(S)-glutamic acids were the most active compounds.
Postovsky Institute of Organic Synthesis, Russian Academy of Sciences (Ural Branch), 22, S. Kovalevskoy St., Ekaterinburg 620990, Russia. Electronic address: ca@ios.uran.ru.
Victor P
VP
Krasnov
Postovsky Institute of Organic Synthesis, Russian Academy of Sciences (Ural Branch), 22, S. Kovalevskoy St., Ekaterinburg 620990, Russia.
Alexey Yu
AY
Vigorov
Postovsky Institute of Organic Synthesis, Russian Academy of Sciences (Ural Branch), 22, S. Kovalevskoy St., Ekaterinburg 620990, Russia.
Vera V
VV
Musiyak
Postovsky Institute of Organic Synthesis, Russian Academy of Sciences (Ural Branch), 22, S. Kovalevskoy St., Ekaterinburg 620990, Russia.
Irina A
IA
Nizova
Postovsky Institute of Organic Synthesis, Russian Academy of Sciences (Ural Branch), 22, S. Kovalevskoy St., Ekaterinburg 620990, Russia.
Dmitry A
DA
Gruzdev
Postovsky Institute of Organic Synthesis, Russian Academy of Sciences (Ural Branch), 22, S. Kovalevskoy St., Ekaterinburg 620990, Russia.
Tatyana V
TV
Matveeva
Postovsky Institute of Organic Synthesis, Russian Academy of Sciences (Ural Branch), 22, S. Kovalevskoy St., Ekaterinburg 620990, Russia.
Galina L
GL
Levit
Ural Research Institute for Phthisiopulmonology, 50, 22 Parts'ezda St., Ekaterinburg 620039, Russia.
Marionella A
MA
Kravchenko
Ural Research Institute for Phthisiopulmonology, 50, 22 Parts'ezda St., Ekaterinburg 620039, Russia.
Sergey N
SN
Skornyakov
Vavilov Institute of General Genetics, Russian Academy of Sciences, 3, Gubkina St., Moscow 119991, Russia.
Olga B
OB
Bekker
Vavilov Institute of General Genetics, Russian Academy of Sciences, 3, Gubkina St., Moscow 119991, Russia.
Valery N
VN
Danilenko
Postovsky Institute of Organic Synthesis, Russian Academy of Sciences (Ural Branch), 22, S. Kovalevskoy St., Ekaterinburg 620990, Russia.
Valery N
VN
Charushin
D000596:Amino Acids / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D004151:Dipeptides / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D004305:Dose-Response Relationship, Drug; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D009161:Mycobacterium / Q000187:drug effects*; D013329:Structure-Activity Relationship
D000596:Amino Acids; D000900:Anti-Bacterial Agents; D004151:Dipeptides
Amino acids; Antimycobacterial activity; Cytotoxicity; Glutamic acid; Purine