Application of 2-Substituted Ethyl Isothiocyanates and 2-Aminothiols in the Synthesis of the Analogs of Indole Phytoalexin Camalexin

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Title:Application of 2-Substituted Ethyl Isothiocyanates and 2-Aminothiols in the Synthesis of the Analogs of Indole Phytoalexin Camalexin
Creators:
Dzurilla, Milan
Ružinský, Martin
Kutschy, Peter
Tewari, Jalpa P.
Kováčik, Vladimír
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 64, 9, pp. 1448-1456
Uncontrolled Keywords:Antifungal activity, Benzocamalexin, Phytoalexins, Indoles, Dihydrocamalexin

Abstract

Treatment of (indol-1-yl)magnesium bromide or iodide with 2-bromoethyl isothiocyanate afforded 1-(4,5-dihydrothiazol-2-yl)indole (<strong>6</strong>). Analogous reaction with 2,2-dimethoxyethyl isothiocyanate led to corresponding 1-thiocarbamoylindole derivative (<strong>7</strong>), which was cyclized to 1-(5-methoxy-4,5-dihydrothiazol-2-yl)indole (<strong>8</strong>) by treatment with boron trifluoride etherate. New analogs of camalexin, namely 4',5'-dihydrocamalexin (<strong>12</strong>) and benzocamalexin (<strong>14</strong>) were prepared by cyclocondensation reaction of 1-(<i>tert</i>-butoxycarbonyl)indole-3-carbaldehyde with cysteamine and 2-aminobenzenethiol. Antifungal activity of the prepared compounds was studied, using the fungi <i>Alternaria brassicae </i>and <i>Alternaria brassicicola</i>. <p>

Title:Application of 2-Substituted Ethyl Isothiocyanates and 2-Aminothiols in the Synthesis of the Analogs of Indole Phytoalexin Camalexin
Creators:
Dzurilla, Milan
Ružinský, Martin
Kutschy, Peter
Tewari, Jalpa P.
Kováčik, Vladimír
Uncontrolled Keywords:Antifungal activity, Benzocamalexin, Phytoalexins, Indoles, Dihydrocamalexin
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:64
Number:9
Page Range:pp. 1448-1456
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19991448UNSPECIFIED
ID Code:1569
Item Type:Article
Deposited On:06 Feb 2009 17:10
Last Modified:06 Feb 2009 16:10

Citation

Dzurilla, Milan; Ružinský, Martin; Kutschy, Peter; Tewari, Jalpa P.; Kováčik, Vladimír (1999) Application of 2-Substituted Ethyl Isothiocyanates and 2-Aminothiols in the Synthesis of the Analogs of Indole Phytoalexin Camalexin. Collection of Czechoslovak Chemical Communications, 64 (9). pp. 1448-1456. ISSN 0010-0765

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