Synthesis, crystal structure and biological activity screening of novel N-(α-bromoacyl)-α-amino esters containing valyl moiety

Authors

  • Denista Yancheva Institute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, Acad. G. Bonchev Str., build. 9, 1113 Sofia
  • Emiliya Cherneva Department of Chemistry, Faculty of Pharmacy, Medical University of Sofia, 2 Dunav Str., 1000 Sofia
  • Markus Quick Institute of Pharmacy, Pharmaceutical Biology, University of Regensburg, Universitätstrasse 31, 93053 Regensburg
  • Bozhanka Mikhova Institute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, Acad. G. Bonchev Str., build. 9, 1113 Sofia
  • Boris Shivachev Institute of Mineralogy and Crystallography "Acad. Ivan Kostov", Bulgarian Academy of Sciences, Acad G. Bonchev Str. build. 107, 1113 Sofia
  • Rosica Nikolova Institute of Mineralogy and Crystallography "Acad. Ivan Kostov", Bulgarian Academy of Sciences, Acad G. Bonchev Str. build. 107, 1113 Sofia
  • Aleksandra Djordjevic Department of Chemistry, Faculty of Science and Mathematics, University of Nis, 18000 Nis
  • Monika Untergehrer Institute of Pharmacy, Pharmaceutical Biology, University of Regensburg, Universitätstrasse 31, 93053 Regensburg
  • Guido Jürgenliemk Institute of Pharmacy, Pharmaceutical Biology, University of Regensburg, Universitätstrasse 31, 93053 Regensburg
  • Birgit Kraus Institute of Pharmacy, Pharmaceutical Biology, University of Regensburg, Universitätstrasse 31, 93053 Regensburg
  • Andrija Smelcerovic Department of Chemistry, Faculty of Medicine, University of Nis, Bulevar Dr Zorana Djindjica 81, 18000 Nis

DOI:

https://doi.org/10.17344/acsi.2015.1418

Keywords:

N-(α-bromoacyl)-α-amino esters, X-ray structure, cytotoxicity, anti-inflammatory activity, antibacterial activity

Abstract

Three novel N-(α-bromoacyl)-α-amino esters, methyl 2-(2-bromo-3-methylbutanamido)pentanoate (1), methyl 2-(2-bromo-3-methylbutanamido)-2-phenylacetate (2) and methyl 2-(2-bromo-3-methylbutanamido)-3-phenylpropanoate (3) were synthesized. Single crystal X-ray diffraction data are reported for compounds 1 and 2. The cytotoxicity, anti-inflammatory and antibacterial activity of compounds 1-3 were investigated. Additionally, the physico-chemical properties of studied compounds were calculated and an in silico toxicological study of compounds 1-3 was performed. The low level of cytotoxicity and absence of antibacterial and anti-inflammatory activity of 1-3 in tested concentrations might be a beneficial prerequisite for their incorporation in prodrugs.

Author Biography

Rosica Nikolova, Institute of Mineralogy and Crystallography "Acad. Ivan Kostov", Bulgarian Academy of Sciences, Acad G. Bonchev Str. build. 107, 1113 Sofia


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Published

17.07.2015

Issue

Vol. 62 No. 3 (2015)

Section

Organic chemistry

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Except where otherwise noted, articles in this journal are published under the Creative Commons Attribution 4.0 International License