Events The 4th International Electronic Conference on Synthetic Organic Chemistry

Event submissions

Published

10.3390/ecsoc-4-01921

This submission belongs to the session c. Bioorganic Chemistry and Natural Products of the event The 4th International Electronic Conference on Synthetic Organic Chemistry

Published date

11 Sep, 2000

Citation

Jiri Kunes, Katarina Kralova, Jiri Hartl, Miroslav Miletin, Martin Dolezal, Synthesis of Some Anilides of Substituted Pyrazine-2-carboxylic Acids and Their Photosynthesis-inhibiting Activity, in Proceedings of The 4th International Electronic Conference on Synthetic Organic Chemistry, 1 November–30 November 2000, MDPI: Basel, Switzerland, doi: 10.3390/ecsoc-4-01921

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Synthesis of Some Anilides of Substituted Pyrazine-2-carboxylic Acids and Their Photosynthesis-inhibiting Activity

Martin Dolezal ¹

Miroslav Miletin ¹

Jiri Hartl ¹

Katarina Kralova ²

Jiri Kunes ³

1. Department of Pharmaceutical Chemistry and Drug Control, Faculty of Pharmacy, Charles University, 500 05 Hradec Kralove, Czech Republic

2. Institute of Chemistry, Faculty of Natural Sciences, Comenius University, 842 15 Bratislava, Slovak Republic

3. Department of Inorganic and Organic Chemistry, Faculty of Pharmacy, Charles University, 500 05 Hradec Kralove, Czech Republic

Abstract

Condensation of chlorides of substituted pyrazine-2-carboxylic acids with ring substituted anilines yielded a series of anilides of 6-chloropyrazine-2-carboxylic, 5-(1,1-dimethylethyl)-pyrazine-2-carboxylic or 6-chloro-5-(1,1-dimethylethyl)pyrazine-2-carboxylic acids. Products were tested for their photosynthesis-inhibiting activity. The most active inhibitor of oxygen evolution rate in spinach chloroplasts was 3,5-bis(trifluoromethyl)anilide of 6-chloropyrazine-2-carboxylic acid (IC50 = 0.026 mmol dm-3), the most active antialgal compound was 3-methylanilide of 6-chloro-5-(1,1dimethylethyl)pyrazine-2-carboxylic acid (IC50 = 0.063 mmol dm-3). The elimination of phenolic group in the benzene moiety led to an decreased photosynthesis-inhibitory activity.

Keywords

Anilides of 6-chloro-5-alkylpyrazine-2-carboxylic acids

Photosynthesis inhibition

Spinach chloroplasts

Chlorella vulgaris.

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