113866-44-7Relevant articles and documents
THE CHEMISTRY OF 1-HYDROXYINDOLE DERIVATIVES: NUCLEOPHILIC SUBSTITUTION REACTIONS ON INDOLE NUCLEUS
Somei, Masanori,Kawasaki, Toshiya,Fukui, Yoshikazu,Yamada, Fumio,Kobayashi, Tetsuya,et al.
, p. 1877 - 1884 (1992)
Nucleophilic substitution reactions were newly found to occur generally in the chemistry of 1-hydroxyindole derivatives.Its application to the synthesis of a phytoalexin, brassicanal A, is reported.
Biotransformation of the Brassica Phytoalexin Brassicanal A by the Blackleg Fungus
Pedras, M. Soledade C.,Khan, Abdul Q.
, p. 3403 - 3407 (1996)
The biotransformation of the brassica phytoalexin brassicanal A by the blackleg fungus [Leptosphaeria maculans (Desm.) Ces. et de Not., asexual stage Phoma lingam (Tode ex Fr.) Desm] was investigated. Three main biotransformation products were detected and isolated; their chemical structures were determined by spectroscopic methods and concomitant synthesis. Additionally, the antifungal activities of brassicanal A and its biotransformation products were compared. Overall, the biotransformation pathway suggests that the blackleg fungus has enzymes to carry out this biotransformation different from those involved in the biotransformation of the brassica phytoalexin brassinin.
Strategies of cruciferous pathogenic fungi: Detoxification of the phytoalexin cyclobrassinin by mimicry
Pedras, M. Soledade C.,Okanga, Francis I.
, p. 1196 - 1202 (1999)
The remarkable metabolism of the cruciferous phytoalexin cyclobrassinin by the phytopathogenic root rot (Rhizoctonia solani Kuhn) and blackleg [Phoma lingam (Tode ex Fr.) Desm., asexual stage of Leptosphaeria maculans (Desm.) Ces. et de Not.] fungi is reported. It was established that R. solani metabolized and detoxified cyclobrassinin via the phytoalexin brassicanal A, which was further transformed into nontoxic products. Detoxification of cyclobrassinin in P. lingam avirulent isolate unity occurred via the phytoalexin brassilexin, whereas the detoxification in P. lingam virulent isolate BJ 125 occurred via the phytoalexin dioxibrassinin. The chemistry involved in the structure determination of the intermediates of these three apparently different pathways and their antifungal activities are described. In addition, efficient syntheses of both phytoalexins brassicanal A and brassilexin by mimicry of the fungal biotransformation route are reported. Implications of these unprecedented transformations are discussed.
Derivatives of thiourea and thiosemicarbazide. Structure, transformations, and pharmacological activity: VII. Synthesis of 2-mercaptopyrimido[4,5-b]indole and 2-mercaptoindole-3-carbaldehyde derivatives
Tomchin,Marysheva
, p. 1060 - 1068 (2007/10/03)
2-Mercaptopyrimido[4,5-b]indole and 2-mercaptoindole-3-carbaldehyde derivatives were synthesized for the first time by reaction of 2-imino-9H-1,3-thiazino[6,5-b]indole with alkyl halides in alkaline medium. The alkylation is preceded by transformation of the thiazine ring into pyrimidine and cleavage of the latter with addition of water molecule and elimination of cyanamide. Attempts to obtain 2-mercaptopyrimido[4,5-b]indole or its 5-methyl derivative by cyclization of N-(2-oxo-2,3-dihydroindol-3-ylmethylene)-thiourea or its S-methyl derivative were unsuccessful. N-(2-Oxo-2,3-dihydroindol-3-ylmethylene)thiourea underwent cleavage of the C=N bond in the side chain.
