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 / Belskaya Nataliya P.,Lugovik Kseniya I.,Bakulev Vasiliy A.,Bauer Jenny,Kitanovic Igor,Holenya Pavlo,Zakhartsev Maksim,Woelfl Stefan // EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY. - 2016. - V. 108, l. . - P. 245-257.

ISSN/EISSN:

0223-5234 / 1768-3254

Type:

Article

Abstract:

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. (C) 2015 Elsevier Masson SAS. All rights reserved.

Author keywords:

3-Hydrazonoindoline-2-thiones; Oxidative cyclization; 1,2,3-Thiadiazolo{[}5,4-b]indoles; Apoptosis induction; Antiproliferative activity CELL-DEATH; OXIDATIVE CYCLIZATION; INDOLE-DERIVATIVES; INHIBITORS; APOPTOSIS; 1,2,3-THIADIAZOLE; COMPLEX; POTENT; REARRANGEMENT; REPLICATION

DOI:

10.1016/j.ejmech.2015.11.011

Web of Science ID:

ISI:000369191800021

Соавторы в МНС:

Другие поля

Поле	Значение
Month	JAN 27
Publisher	ELSEVIER FRANCE-EDITIONS SCIENTIFIQUES MEDICALES ELSEVIER
Address	23 RUE LINOIS, 75724 PARIS, FRANCE
Language	English
EISSN	1768-3254
Keywords-Plus	CELL-DEATH; OXIDATIVE CYCLIZATION; INDOLE-DERIVATIVES; INHIBITORS; APOPTOSIS; 1,2,3-THIADIAZOLE; COMPLEX; POTENT; REARRANGEMENT; REPLICATION
Research-Areas	Pharmacology \& Pharmacy
Web-of-Science-Categories	Chemistry, Medicinal
Author-Email	n.p.belskaya@urfu.ru maksim.zakhartsev@uni-hohenheim.de
ResearcherID-Numbers	Belskaya, Nataliya/S-3953-2017
ORCID-Numbers	Belskaya, Nataliya/0000-0002-2509-7916
Number-of-Cited-References	51
Usage-Count-Last-180-days	2
Usage-Count-Since-2013	10
Journal-ISO	Eur. J. Med. Chem.
Doc-Delivery-Number	DC4LG