Synthesis and Cytotoxic Properties of Halogen and Aryl-/Heteroarylpiperazinyl Derivatives of Benzofurans

Author(s):

Mariola Krawiecka, Bozena Kuran, Jerzy Kossakowski, Marcin Cieslak, Julia Kazmierczak- Baranska, Karolina Krolewska and Barbara Nawrot   Pages 115 - 121 ( 7 )

Abstract:

A series of seven derivatives of 1,1'-(5,6-dimethoxy-3-methyl-1-benzofuran-2,7-diyl)diethanone was synthesized and characterized by ¹HNMR and ESI MS spectra and elemental analyses. The obtained new compounds and three halogen derivatives of benzofuran, reported in our earlier work, were tested for their cytotoxic properties in human chronic (K562) and acute (HL60) leukemia cells, human cervical cancer (HeLa), and normal endothelial cells (HUVEC). Four compounds (2, 3, 4, 5), which contain halogens in their structure showed significant anticancer activity. The most promising was 1,1'-[3- (bromomethyl)-5,6-dimethoxy-1-benzofuran-2,7-diyl]diethanone (2), which was highly and selectively toxic for K562 cells (IC₅₀ of 5µM) and HL60 cells (IC₅₀ of 0.1µM), which showed no cytotoxicity toward HeLa and HUVEC cells. Moreover, the observed remarkable cytotoxicity of this compound toward K562 cells resulted from cells apoptosis.

Keywords:

Apoptosis, benzofurans, cytotoxic properties, HeLa, HL60, K562.

Affiliation:

Department of Biochemistry, Medical University of Warsaw, 1 Banacha Str., 02-097 Warsaw, Poland.

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