Synthesis of Camalexin
| Autor: | M. Dzurilla, M. Ruzinsky, P. Kutschy, J. Zaletova, V. Kovacik |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2001 |
| Předmět: |
phytoalexins
Decarboxylation Stereochemistry Pharmaceutical Science Article Analytical Chemistry lcsh:QD241-441 lcsh:Organic chemistry Camalexin Drug Discovery Arabidopsis thaliana Physical and Theoretical Chemistry Indole test chemistry.chemical_classification biology Chemistry Phytoalexin Organic Chemistry Carbon-13 NMR indoles biology.organism_classification Alternaria brassicae Chemistry (miscellaneous) Proton NMR Molecular Medicine |
| Zdroj: | Molecules : A Journal of Synthetic Chemistry and Natural Product Chemistry Molecules, Vol 6, Iss 9, Pp 716-720 (2001) Molecules Volume 6 Issue 9 Pages 716-720 |
| ISSN: | 1420-3049 |
| Popis: | In this paper we describe a new method for the synthesis of camalexin ( 1 )based on the reaction of 1-(tert-butoxycarbonyl)indole-3-carboxaldehyde with methyl L-cysteinate hydrochloride, followed by oxidation and decarboxylation. Compounds 1 , andintermediates 5 - 7 were identified by elemental analysis, 1 H NMR, 13 C NMR and massspectroscopy. Keywords: Camalexin, phytoalexins, indoles Introduction Camalexin [3-(2 ’ -thiazolyl)indole] ( 1 ) is a natural phytoalexin, isolated for the first time from theleaves of Camelina sativa and elicited by the fungus Alternaria brassicae [1]. Camalexin is also theprincipal phytoalexin found in Arabidopsis thaliana [2]. It exhibits antifungal activity similar to thesystemic fungicide thiabendazole ( 2 ) [1,3] and also has antitumor activity [4]. In the literature there aredescribed four methods for synthesis of camalexin, based on the reaction of indolylmagnesium iodidewith 2-bromothiazole [3], heating of indole-3-carboxamide with P 2 S |
| Databáze: | OpenAIRE |
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