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The new facile and straightforward method for the synthesis of 4H-1,2,3-thiadiazolo[5,4-b]indoles and determination of their antiproliferative activity

A series of 4H-1,2,3-thiadiazolo[5,4-b]indoles were synthesized by novel tandem of oxidative cyclization of 3-alkoxycarbonylhydrazonoindoline-2-thiones, 1,5-H-shift and elimination of tert-butoxy(ethoxy)carbonyl group. The simple method for their modifications by the reactions with electrophilic age...

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Main Authors: Belskaya, Nataliya P. (Author) , Lugovik, Kseniya I. (Author) , Bakulev, Vasiliy A. (Author) , Bauer, Jenny (Author) , Kitanovic, Igor (Author) , Holenya, Pavlo (Author) , Zakhartsev, Maksim (Author) , Wölfl, Stefan (Author)
Format: Article (Journal)
Language:English
Published: 2016
In: European journal of medicinal chemistry
Year: 2015, Volume: 108, Pages: 245-257
ISSN:1768-3254
DOI:10.1016/j.ejmech.2015.11.011
Online Access:Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1016/j.ejmech.2015.11.011
Verlag, lizenzpflichtig, Volltext: http://www.sciencedirect.com/science/article/pii/S0223523415303482
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Author Notes:Nataliya P. Belskaya, Kseniya I. Lugovik, Vasiliy A. Bakulev, Jenny Bauer, Igor Kitanovic, Pavlo Holenya, Maksim Zakhartsev, Stefan Wölfl
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Summary:A series of 4H-1,2,3-thiadiazolo[5,4-b]indoles were synthesized by novel tandem of oxidative cyclization of 3-alkoxycarbonylhydrazonoindoline-2-thiones, 1,5-H-shift and elimination of tert-butoxy(ethoxy)carbonyl group. The simple method for their modifications by the reactions with electrophilic agents were elaborated and as a result of the synthetic investigation a number of N-alkyl-, N-acyl- and N-sulfonyl-4H-1,2,3-thiadiazolo[5,4-b]indoles were prepared in good yields. Preliminary biological tests for the three examples of synthesized compounds with different substituents at the nitrogen atom indole ring have shown that the biological behavior of the investigated 1,2,3-thiadiazolo[5,4-b]indoles is substantially directed by this structural fragment.
Item Description:Online 11 November 2015
Gesehen am 05.05.2020
Physical Description:Online Resource
ISSN:1768-3254
DOI:10.1016/j.ejmech.2015.11.011

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