title: 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.
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.
authors.affiliation: Ural Federal University, Mira Str. 19, Ekaterinburg 620002, Russia. Electronic address: n.p.belskaya@urfu.ru.
authors.forename: Nataliya P
authors.initials: NP
authors.lastname: Belskaya
authors.affiliation: Ural Federal University, Mira Str. 19, Ekaterinburg 620002, Russia.
authors.forename: Kseniya I
authors.initials: KI
authors.lastname: Lugovik
authors.affiliation: Ural Federal University, Mira Str. 19, Ekaterinburg 620002, Russia; Institute of Pharmacology and Molecular Biotechnology, University of Heidelberg, Im Neuenheimer Feld 364, 69120 Heidelberg, Germany.
authors.forename: Vasiliy A
authors.initials: VA
authors.lastname: Bakulev
authors.affiliation: Institute of Pharmacology and Molecular Biotechnology, University of Heidelberg, Im Neuenheimer Feld 364, 69120 Heidelberg, Germany.
authors.forename: Jenny
authors.initials: J
authors.lastname: Bauer
authors.affiliation: Institute of Pharmacology and Molecular Biotechnology, University of Heidelberg, Im Neuenheimer Feld 364, 69120 Heidelberg, Germany.
authors.forename: Igor
authors.initials: I
authors.lastname: Kitanovic
authors.affiliation: Institute of Pharmacology and Molecular Biotechnology, University of Heidelberg, Im Neuenheimer Feld 364, 69120 Heidelberg, Germany.
authors.forename: Pavlo
authors.initials: P
authors.lastname: Holenya
authors.affiliation: Institute of Pharmacology and Molecular Biotechnology, University of Heidelberg, Im Neuenheimer Feld 364, 69120 Heidelberg, Germany. Electronic address: maksim.zakhartsev@uni-hohenheim.de.
authors.forename: Maksim
authors.initials: M
authors.lastname: Zakhartsev
authors.affiliation: Institute of Pharmacology and Molecular Biotechnology, University of Heidelberg, Im Neuenheimer Feld 364, 69120 Heidelberg, Germany.
authors.forename: Stefan
authors.initials: S
authors.lastname: Wölfl
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D017209:Apoptosis / Q000187:drug effects; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D004305:Dose-Response Relationship, Drug; D004354:Drug Screening Assays, Antitumor; D057809:HEK293 Cells; D006801:Humans; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D008958:Models, Molecular; D015394:Molecular Structure; D013329:Structure-Activity Relationship; D013830:Thiadiazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
chemical_list: D000970:Antineoplastic Agents; D007211:Indoles; D013830:Thiadiazoles
keywords: 1,2,3-Thiadiazolo[5,4-b]indoles; 3-Hydrazonoindoline-2-thiones; Antiproliferative activity; Apoptosis induction; Oxidative cyclization