Skip to main content

Structure-activity relationships of novel heteroaryl-acrylonitriles as cytotoxic and antibacterial agents.

Saczewski, Franciszek, Stencel, Agnieszka, Bie?czak, Andrzej M, Langowska, Karolina A, Michaelis, Martin, Werel, W?adys?aw, Ha?asa, Rafa?, Reszka, Przemyslaw, Bednarski, Patrick J (2008) Structure-activity relationships of novel heteroaryl-acrylonitriles as cytotoxic and antibacterial agents. European Journal of Medicinal Chemistry, 43 (9). pp. 1847-57. ISSN 0223-5234. (The full text of this publication is not currently available from this repository. You may be able to access a copy if URLs are provided)

The full text of this publication is not currently available from this repository. You may be able to access a copy if URLs are provided. (Contact us about this Publication)

Abstract

Eighteen new 2,6-disubstituted acrylonitriles and two new (benzimidazol-1-yl)-acetamide derivatives were prepared and screened for antibacterial and cytotoxic activities on 12 human cancer cell lines. Based on the lead structure 2-(benzimidazol-2-yl)-3-(5-nitrothiophen-2-yl) acrylonitrile it was found that placement of methyl groups at the 5,6 positions of the benzimidazole ring lead to a 3-fold increase in overall cytotoxic activity. Replacing the nitrothiophene for pyridine reduced cytotoxic activity as did replacing the nitro group for a methoxy group. Cytotoxic activity was only slightly reduced when the benzimidazole ring was replaced by a imidazo[4,5-b]pyridine or a benzthiazole ring but replacement by benzoxazole led to a substantial decrease in activity. Moving the acrylonitrile group from position 2 to position 1 of the benzimidazole ring also resulted in moderately active compounds. (Benzimidazol-1-yl)acetamides showed only modest activity. The structure-activity relationships found in the cytotoxicity studies are mirrored in the results of the antibacterial experiments.

Item Type: Article
Subjects: R Medicine > RM Therapeutics. Pharmacology
Divisions: Faculties > Sciences > School of Biosciences
Depositing User: Martin Michaelis
Date Deposited: 05 Jun 2013 19:54 UTC
Last Modified: 29 May 2019 10:15 UTC
Resource URI: https://kar.kent.ac.uk/id/eprint/34133 (The current URI for this page, for reference purposes)
  • Depositors only (login required):