Synthesis of polybrominated benzimidazole and benzotriazole derivatives containing a tetrazole ring and their cytotoxic activity

Edyta Łukowska-Chojnacka , Patrycja Wińska , Monika Wielechowska , Maria Bretner

Abstract

A series of new benzimidazole and benzotriazole derivatives containing a tetrazole moiety was synthesized by N-alkylation of 5-aryltetrazole with 4,5,6,7-tetrabromo- 1-(3-chloropropyl)-1H-benzimidazole and 4,5,6,7-tetrabromo- 2-(3-chloropropyl)-2H-benzotriazole. The reaction was regioselective and mostly 2,5-disubstituted tetrazole derivatives were obtained. The effect of all synthesized compounds on human recombinant casein kinase 2alpha subunit (rhCK2a) and cytotoxicity against human T-cell lymphoblast (CCRF-CEM) and breast adenocarcinoma (MCF-7) cell lines were evaluated. The results have shown that many of the synthesized compounds exhibit significant cytotoxicity at micromolar concentration.
Author Edyta Łukowska-Chojnacka ZTiBSL
Edyta Łukowska-Chojnacka,,
- Department Of Drug Technology And Biotechnology
, Patrycja Wińska ZTiBSL
Patrycja Wińska,,
- Department Of Drug Technology And Biotechnology
, Monika Wielechowska ZTiBSL
Monika Wielechowska,,
- Department Of Drug Technology And Biotechnology
, Maria Bretner ZTiBSL
Maria Bretner,,
- Department Of Drug Technology And Biotechnology
Journal seriesMonatshefte Fur Chemie, ISSN 0026-9247
Issue year2016
Vol147
No10
Pages1789-1796
Publication size in sheets0.5
Keywords in EnglishAntitumor agents; Azole; Benzimidazole Heterocycles; Tetrazole Total synthesis Int
DOIDOI:10.1007/s00706-016-1785-8
URL https://www.ncbi.nlm.nih.gov/pubmed/27729714
Languageen angielski
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Score (nominal)25
ScoreMinisterial score = 20.0, 28-11-2017, ArticleFromJournal
Ministerial score (2013-2016) = 25.0, 28-11-2017, ArticleFromJournal
Publication indicators WoS Impact Factor: 2016 = 1.282 (2) - 2016=1.224 (5)
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