- 2-(Substituted phenyl)amino analogs of 1-methoxyspirobrassinol methyl ether: Synthesis and anticancer activity
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New analogs of indole phytoalexin 1-methoxyspirobrassinol methyl ether have been designed by replacement of its 2-methoxy group with 2-(substituted phenyl)amino group. Synthesized by spirocyclization methodology, trans- and cis-diastereoisomers of target
- Kutschy, Peter,Salayova, Aneta,Curillova, Zuzana,Kozar, Tibor,Mezencev, Roman,Mojzis, Jan,Pilatova, Martina,Balentova, Eva,Pazdera, Pavel,Sabol, Marian,Zburova, Michaela
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- A novel palladium-catalyzed cyclization of indole phytoalexin brassinin and its 1-substituted derivatives
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A novel simple synthetic approach to spiroindoline phytoalexins and their derivatives has been developed. The spirocyclization of brassinin and its 1-substituted derivatives was achieved using palladium catalyst PdCl 2(CH3CN)2 in DMSO at 80°C in the presence of water, methanol or aniline.
- Budovska, Mariana
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- Sinalbins A and B, phytoalexins from Sinapis alba: Elicitation, isolation, and synthesis
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The chemical structure and synthesis of sinalbin A is described. This cruciferous phytoalexin is produced by white mustard (Sinapis alba) after treatment with biotic and abiotic elicitors. In addition, a related metabolite, named sinalbin B, is present in extracts from elicited plants, but not in those from non-elicited controls. Sinalbin B, which was also synthesized appears to be both a phytoalexin and a biosynthetic precursor of sinalbin A. (C) 2000 Elsevier Science Ltd.
- Pedras, M.Soledade C,Zaharia, Irina L
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- Initial and Final Products, Nitriles, and Ascorbigens Produced in Myrosinase-Catalyzed Hydrolysis of Indole Glucosinolates
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Micellar electrokinetic capillary chromatography (MECC) was used to follow the myrosinase (β-thioglucoside glucohydrolase EC 3.2.3.1)-catalyzed transformation of glucobrassicin (indol-3-ylmethylglucosinolate, 1a) and neoglucobrassicin (N-methoxyglucobrassicin, 1b) into nitriles, ascorbigens, and other products. The influence of pH, ascorbic acid, and Fe(II) ions was investigated. In the presence of ascorbic acid, (5 mM), thiocyanate ion and ascorbigens were the dominating products from 1a and 1b. In the presence of Fe(II) ions (2.5 mM), nitriles were the dominating products between pH 4 and 6-7. During hydrolysis of 1b in neutral or weakly basic solution, an unstable intermediate was detected by MECC. Comparisons of the rate of ascorbigen formation from 1a, 1b, and indol-3-ylcarbinol showed that ascorbigens were formed directly from ascorbate and unstable products of the hydrolysis of indole glucosinolates and that indol-3-ylcarbinols were not important intermediates. Structures of 1a, 1b, and products of 1b were confirmed by 1H NMR, MS, and UV spectroscopy.
- Agerbirk, Niels,Olsen, Carl Erik,Sorensen, Hilmer
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p. 1563 - 1571
(2007/10/03)
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- A SIMPLE SYNTHESIS OF A PHYTOALEXIN, METHOXYBRASSININ
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A simple and an alternative multi-gram scale synthetic method methoxybrassinin is developed starting from indole-3-carboxaldehyde.
- Somei, Masanori,Kobayashi, Kensuke,Shimizu, Kazuhisa,Kawasaki, Toshiya
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- THE FIRST TOTAL SYNTHESES OF 9-METHOXYCARBAZOLE-3-CARBOXALDEHYDE AND METHOXYBRASSININ (THE CHEMISTRY OF 1-METHOXYINDOLE)
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The first total syntheses of an alkaloid 9-methoxycarbazole-3-carboxaldehyde and a phytoalexin methoxybrassinin are reported.
- Kawasaki, Toshiya,Somei, Masanori
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p. 1605 - 1608
(2007/10/02)
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- Chemistry of Indole Glucosinolates: Intermediacy of Indol-3-ylmethyl Isothiocyanates in the Enzymic Hydrolysis of Indole Glucosinolates
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The enzymic hydrolysis of 1-methoxyindol-3-ylmethyl glucosinolate (1b) proceeds via the corresponding isothiocyanate (2b), thus providing evidence for a previously unsubstantiated breakdown pathway and establishing a link with 1-methoxycyclobrassinin (4b) and related indole phytoalexins.
- Hanley, A. Bryan,Parsley, Keith R.,Lewis, Jenny A.,Fenwick, G. Roger
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p. 2273 - 2276
(2007/10/02)
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