Next Article in Journal
Fabrication of Mesoporous Silica Shells on Solid Silica Spheres Using Anionic Surfactants and Their Potential Application in Controlling Drug Release
Previous Article in Journal
Spiculisporic Acids B–D, Three New γ-Butenolide Derivatives from a Sea Urchin-Derived Fungus Aspergillus sp. HDf2
Article Menu

Export Article

Open AccessArticle
Molecules 2012, 17(11), 13183-13198; doi:10.3390/molecules171113183

Substituted N-Benzylpyrazine-2-carboxamides: Synthesis and Biological Evaluation

1
Department of Pharmaceutical Chemistry and Drug Control, Faculty of Pharmacy, Charles University in Prague, Heyrovského 1203, 500 05 Hradec Králové, Czech Republic
2
Department of Biophysics and Physical Chemistry, Faculty of Pharmacy, Charles University in Prague, Heyrovského 1203, 500 05 Hradec Králové, Czech Republic
3
Department of Clinical Microbiology, University Hospital, Sokolská 581, 500 05 Hradec Králové, Czech Republic
4
Department of Ecosozology and Physiotactics, Faculty of Natural Sciences, Comenius University, Mlynská Dolina Ch-2, 84215 Bratislava, Slovakia
5
Institute of Chemistry, Faculty of Natural Sciences, Comenius University, Mlynská Dolina CH-2, 842 15 Bratislava, Slovakia
Preliminary results related to the topic of this article were presented at The Fifteenth International Electronic Conference on Synthetic Organic Chemistry (ECSOC-15, https://docs.google.com/ viewer?url=http://www.sciforum.net/presentation/599/pdf&chrome=true), 1–30 November 2011.
*
Author to whom correspondence should be addressed.
Received: 22 October 2012 / Revised: 31 October 2012 / Accepted: 2 November 2012 / Published: 6 November 2012
(This article belongs to the Section Medicinal Chemistry)
View Full-Text   |   Download PDF [359 KB, uploaded 18 June 2014]   |  

Abstract

A series of twelve amides was synthesized via aminolysis of substituted pyrazinecarboxylic acid chlorides with substituted benzylamines. Compounds were characterized with analytical data and assayed in vitro for their antimycobacterial, antifungal, antibacterial and photosynthesis-inhibiting activity. 5-tert-Butyl-6-chloro-N-(4-methoxybenzyl)pyrazine-2-carboxamide (12) has shown the highest antimycobacterial activity against Mycobacterium tuberculosis (MIC = 6.25 µg/mL), as well as against other mycobacterial strains. The highest antifungal activity against Trichophyton mentagrophytes, the most susceptible fungal strain tested, was found for 5-chloro-N-(3-trifluoromethylbenzyl)-pyrazine-2-carboxamide (2, MIC = 15.62 µmol/L). None of the studied compounds exhibited any activity against the tested bacterial strains. Except for 5-tert-butyl-6-chloro-N-benzylpyrazine-2-carboxamide (9, IC50 = 7.4 µmol/L) and 5-tert-butyl-6-chloro-N-(4-chlorobenzyl)pyrazine-2-carboxamide (11, IC50 = 13.4 µmol/L), only moderate or weak photosynthesis-inhibiting activity in spinach chloroplasts (Spinacia oleracea L.) was detected. View Full-Text
Keywords: pyrazinamide analogues; lipophilicity determination; in vitro antimycobacterial; antifungal and photosynthesis inhibitory activity pyrazinamide analogues; lipophilicity determination; in vitro antimycobacterial; antifungal and photosynthesis inhibitory activity
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

Scifeed alert for new publications

Never miss any articles matching your research from any publisher
  • Get alerts for new papers matching your research
  • Find out the new papers from selected authors
  • Updated daily for 49'000+ journals and 6000+ publishers
  • Define your Scifeed now

SciFeed Share & Cite This Article

MDPI and ACS Style

Servusová, B.; Eibinová, D.; Doležal, M.; Kubíček, V.; Paterová, P.; Peško, M.; Kráľová, K. Substituted N-Benzylpyrazine-2-carboxamides: Synthesis and Biological Evaluation. Molecules 2012, 17, 13183-13198.

Show more citation formats Show less citations formats

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]

Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top