188988-46-7Relevant academic research and scientific papers
The synthesis and anticancer activity of analogs of the indole phytoalexins brassinin, 1-methoxyspirobrassinol methyl ether and cyclobrassinin This work is dedicated to the memory of Associated Professor Peter Kutschy (1953-2012)
Budovska, Mariana,Pilatova, Martina,Varinska, Lenka,Mojzis, Jan,Mezencev, Roman
, p. 6623 - 6633 (2013)
An effective synthesis of analogs of the indole phytoalexin cyclobrassinin with NR1R2 group instead of SCH3 was developed starting from indole-3-carboxaldehyde. The target compounds were prepared by spirocyclization of 1-Boc-thioureas with the formation of isolable spiroindoline intermediates, followed by the trifluoroacetic acid-induced cascade reaction consisting of methanol elimination, deprotection and rearrangement of the iminium ion. The structures of novel products were elucided by the 1H and 13C NMR spectroscopy, including HMBC, HSQC, COSY, NOESY and DEPT measurements. Several newly synthesized compounds demonstrated significant antiproliferative/cytotoxic activity against human leukemia and solid tumor cell lines, as well as remarkable selectivity of these effects against cancer cells relative to the non-malignant HUVEC cells.
Iodine mediated deprotection of N-tert-butanesulfinyl amines: A functional group compatible method
Chen, Wen,Ren, Jian,Wang, Minshou,Dang, Lingjing,Shen, Xianfu,Yang, Xiaodong,Zhang, Hongbin
supporting information, p. 6259 - 6262 (2014/06/09)
In the presence of iodine, a functional group compatible method for the deprotection of tert-butanesulfinyl and p-toluenesulfinyl units was developed. This journal is the Partner Organisations 2014.
A novel palladium-catalyzed cyclization of indole phytoalexin brassinin and its 1-substituted derivatives
Budovska, Mariana
, p. 5575 - 5582 (2014/01/23)
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.
New syntheses of indole phytoalexins and related compounds
Kutschy, Peter,Dzurilla, Milan,Takasugi, Mitsuo,Toeroek, Marcel,Achbergerova, Ingrid,Homzova, Renata,Racova, Maria
, p. 3549 - 3566 (2007/10/03)
Synthesis of indole phytoalexins brassinin, brassitin, cyclobrassinin and related compounds via 3-aminomethylindole and its 1-substituted derivatives obtained by nickel boride catalyzed reduction of corresponding aldoximes with sodium borohydride and via [1-(t-butoxycarbonyl)-indol-3-yl]methyl isothiocyanate, the first stable derivative of indol-3-ylmethyl isothiocyanate is described. Antifungal activity of the prepared compounds was examined by using the fungus Bipolaris leersiae by t.l.c. bioassay and quantitative screening was carried out with the selected compounds.
Synthesis of Indole Phytoalexins Brassinin and Cyclobrassinin via [1-(tert-Butoxycarbonyl)indol-3-yl]-methyl Isothiocyanate as the Key Biomimetic Intermediate
Kutschy, Peter,Achbergerová, Ingrid,Dzurilla, Milan,Takasugi, Mitsuo
, p. 289 - 290 (2007/10/03)
A four-step synthesis of 1-protected indol-3-ylmethyl isothiocyanates from indole-3-carboxaldehyde has been elaborated. [1-(tert-Butoxycarbonyl)indol-3-yl]methyl isothiocyanate appeared to be a suitable biomimetic intermediate for the synthesis of protected phytoalexins brassinin and cyclobrassinin. Removing of the tert-butoxycarbonyl protecting group under specific conditions afforded phytoalexins identical with previously described compounds.
