Next Article in Journal
4a,5,9,10,11,12-Hexahydro-6H-benzo[a]cyclohepta[hi]benzofuran - Synthesis of Unnatural Galanthamine Analogs
Previous Article in Journal
Synthesis of 2,3-Dimethoxy-7-methyl-7,12-dihydro-6H-[1]-benzofuro-[2,3-c]-[1]-benzazepin-6,12-dione
Article Menu

Export Article

Open AccessArticle
Molecules 2002, 7(3), 363-373; doi:10.3390/70300363

Substituted Amides of Pyrazine-2-carboxylic acids: Synthesis and Biological Activity

1
Department of Pharmaceutical Chemistry and Drug Control, Faculty of Pharmacy, Charles University, 500 05 Hradec Králové, Czech Republic
2
Department of Inorganic and Organic Chemistry, Faculty of Pharmacy, Charles University, 500 05 Hradec Králové, Czech Republic
3
Institute of Chemistry, Faculty of Natural Sciences, Comenius University, 842 15 Bratislava, Slovak Republic
*
Author to whom correspondence should be addressed.
Received: 24 October 2001 / Revised: 12 March 2002 / Accepted: 22 March 2002 / Published: 31 March 2002
View Full-Text   |   Download PDF [103 KB, uploaded 18 June 2014]   |  

Abstract

Condensation of 6-chloro-, 5-tert-butyl- or 6-chloro-5-tert-butylpyrazine-2-carboxylic acid chloride with ring substituted anilines yielded a series of amides, which were tested for their in vitro antimycobacterial, antifungal and photosynthesis-inhibiting activities. The highest antituberculotic activity (72% inhibition) against Mycobacterium tuberculosis and the highest lipophilicity (log P = 6.85) were shown by the 3,5-bistrifluoromethylphenyl amide of 5-tert-butyl-6-chloropyrazine-2-carboxylic acid (2o). The 3-methylphenyl amides of 6-chloro- and 5-tert-butyl-6-chloro-pyrazine-2-carboxylic acid (2d and 2f) exhibited only a poor in vitro antifungal effect (MIC = 31.25-500 μmol·dm-3) against all strains tested, although the latter was the most active antialgal compound (IC50 = 0.063 mmol·dm-3). The most active inhibitor of oxygen evolution rate in spinach chloroplasts was the (3,5-bis-trifluoromethylphenyl)amide of 6-chloropyrazine-2-carboxylic acid (2m, IC50 = 0.026 mmol·dm-3). View Full-Text
Keywords: Amides of pyrazinecarboxylic acid; antimycobacterial activity; antifungal evaluation; photosynthesis inhibition Amides of pyrazinecarboxylic acid; antimycobacterial activity; antifungal evaluation; photosynthesis inhibition
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

Dolezal, M.; Miletin, M.; Kunes, J.; Kralova, K. Substituted Amides of Pyrazine-2-carboxylic acids: Synthesis and Biological Activity. Molecules 2002, 7, 363-373.

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