Substituted 2-Styrylquinazoline Derivatives: Preparation and Their Biological Activities

Jaroslaw Polanski; Aidan Coffey; Jim O'Mahony; Jacek Finster; Katarina Kralova; James Carroll; Matus Pesko; Josef Jampilek; Robert Musiol

doi:10.3390/ecsoc-13-00204

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Substituted 2-Styrylquinazoline Derivatives: Preparation and Their Biological Activities

Jaroslaw Polanski

¹,

Aidan Coffey

²,

Jim O'Mahony

²,

Jacek Finster

¹,

Katarina Kralova

³,

James Carroll

²,

Matus Pesko

⁴,

Josef Jampilek

^{*

5, 6},

Robert Musiol

^{*

1}

¹ Institute of Chemistry, University of Silesia, Szkolna 9, 40007 Katowice, Poland
² Department of Biological Sciences, Cork Institute of Technology, Bishopstown, Cork, Ireland
³ Institute of Chemistry, Faculty of Natural Sciences, Comenius University, Mlynska dolina Ch-2, 84215 Bratislava, Slovakia
⁴ Department of Ecosozology and Physiotactics, Faculty of Natural Sciences, Comenius University, Mlynska dolina Ch-2, 84215 Bratislava, Slovakia
⁵ Zentiva a.s., U kabelovny 130, 102 37 Prague 10, Czech Republic
⁶ Department of Chemical Drugs, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences, Palackeho 1/3, 61242 Brno, Czech Republic

Published: 01 November 2009 by MDPI in The 13th International Electronic Conference on Synthetic Organic Chemistry session Bioorganic Chemistry and Natural Products

https://doi.org/10.3390/ecsoc-13-00204

Abstract: In this study, a series of five ring-substituted 2-styrylquinazolin-4(3H)-one and five ring-substituted 4-chloro-2-styrylquinazoline derivatives were prepared. The procedures for synthesis of the compounds are presented. The compounds were analyzed using RP-HPLC to determine lipophilicity. They were tested for their activity related to inhibition of photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts. Primary in vitro screening of the synthesized compounds was also performed against four mycobacterial strains. Several compounds showed biological activity comparable with or higher than the standard isoniazid. For all the compounds, the relationships between the lipophilicity and the chemical structure of the studied compounds are discussed, as well as their structure-activity relationships (SAR).

Keywords: Styrylquinazoline derivatives; Lipophilicity; PET inhibition; Spinach chloroplasts; In vitro antimycobacterial activity; Structure-activity relationships

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