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Bioorg Med Chem Lett. 2016 Jun 1;26(11):2645-8. doi: 10.1016/j.bmcl.2016.04.017. Epub 2016 Apr 9.

Synthesis and antimycobacterial activity of N-(2-aminopurin-6-yl) and N-(purin-6-yl) amino acids and dipeptides.

Author information

1
Postovsky Institute of Organic Synthesis, Russian Academy of Sciences (Ural Branch), 22, S. Kovalevskoy St., Ekaterinburg 620990, Russia. Electronic address: ca@ios.uran.ru.
2
Postovsky Institute of Organic Synthesis, Russian Academy of Sciences (Ural Branch), 22, S. Kovalevskoy St., Ekaterinburg 620990, Russia.
3
Ural Research Institute for Phthisiopulmonology, 50, 22 Parts'ezda St., Ekaterinburg 620039, Russia.
4
Vavilov Institute of General Genetics, Russian Academy of Sciences, 3, Gubkina St., Moscow 119991, Russia.

Abstract

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.

KEYWORDS:

Amino acids; Antimycobacterial activity; Cytotoxicity; Glutamic acid; Purine

PMID:
27107949
DOI:
10.1016/j.bmcl.2016.04.017
[Indexed for MEDLINE]

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