Synthesis and Antituberculotic Activity of 5-Alkyl-6-chloro-2-pyrazinecarboxamides and Corresponding Thioamides

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Title:Synthesis and Antituberculotic Activity of 5-Alkyl-6-chloro-2-pyrazinecarboxamides and Corresponding Thioamides
Creators:
Hartl, Jiří
Doležal, Martin
Krinková, Jana
Lyčka, Antonín
Odlerová, Želmíra
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 61, 7, pp. 1109-1114
Uncontrolled Keywords:Pyrazinecarbothioamides, Pyrazinecarboxamides, Homolytic alkylation, Tuberculostatic activity

Abstract

Homolytic alkylation of 6-chloro-2-pyrazinecarbonitrile by alkanoic acid and subsequent partial hydrolysis afforded 5-alkyl-6-chloro-2-pyrazinecarboxamides <strong>1a-1e</strong>. Reaction of amides <strong>1a-1e</strong> by Lawesson's reagent afforded corresponding thioamides <strong>2a-2e</strong>. The structure of compounds was confirmed by elemental analysis, IR and <sup>1</sup>H NMR spectra. The assessment of in vitro antimycobacterial activity of the compounds was carried out. The highest antituberculotic activity against <i>Mycobacterium tuberculosis</i> and other mycobacterial strains in this series was shown by 5-(1,1-dimethylethyl)-6-chloro-2-pyrazinecarbothioamide (<strong>2e</strong>).

Title:Synthesis and Antituberculotic Activity of 5-Alkyl-6-chloro-2-pyrazinecarboxamides and Corresponding Thioamides
Creators:
Hartl, Jiří
Doležal, Martin
Krinková, Jana
Lyčka, Antonín
Odlerová, Želmíra
Uncontrolled Keywords:Pyrazinecarbothioamides, Pyrazinecarboxamides, Homolytic alkylation, Tuberculostatic activity
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:61
Number:7
Page Range:pp. 1109-1114
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19961109UNSPECIFIED
ID Code:1016
Item Type:Article
Deposited On:06 Feb 2009 17:05
Last Modified:06 Feb 2009 16:05

Citation

Hartl, Jiří; Doležal, Martin; Krinková, Jana; Lyčka, Antonín; Odlerová, Želmíra (1996) Synthesis and Antituberculotic Activity of 5-Alkyl-6-chloro-2-pyrazinecarboxamides and Corresponding Thioamides. Collection of Czechoslovak Chemical Communications, 61 (7). pp. 1109-1114. ISSN 0010-0765

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