Synthesis and evaluation of p - N , N -dialkyl substituted chalcones as anti-cancer agents
- PDF / 328,536 Bytes
- 5 Pages / 595.276 x 790.866 pts Page_size
- 110 Downloads / 180 Views
Med Chem Res (2013) 22:4610–4614 DOI 10.1007/s00044-013-0469-8
ORIGINAL RESEARCH
Synthesis and evaluation of p-N,N-dialkyl substituted chalcones as anti-cancer agents Grady Nelson • Mohammad A. Alam • Tyler Atkinson • Shirisha Gurrapu • J. Sravan Kumar • Chris Bicknese • Joseph L. Johnson • Michael Williams
Received: 23 August 2012 / Accepted: 3 January 2013 / Published online: 16 January 2013 Ó Springer Science+Business Media New York 2013
Abstract Several new N,N-dialkyl substituted chalcones (chalconoids or benzylideneacetophenones) have been synthesized via the condensation of corresponding N,Ndialkylbenzaldehyde with various aryl methyl ketones. All the chalcones have been synthesized from readily available and cheap starting materials under environmentally benign conditions in very high yields without work up and column chromatographic purification. Synthesized compounds have been tested for their biological activity against pathogenic microorganisms such as Escherichia coli, Bacillus subtilis, and Mycobacterium smegmatis. Anti-cancer activity of these compounds has also been tested against multiple myeloma (RPMI-8226) and human mammary adenocarcinoma (MCF-7) cell lines. The most hydrophilic molecules 23 and 24 showed very good anti-cancer activity against MCF-7 cell lines at low micro-molar concentrations. All the compounds have also been evaluated for their activity against Beta-secretase 1 enzyme. One of the synthesized compounds showed Beta-secretase 1 enzyme inhibition activity at micro-molar concentration. Keywords Chalcones Anti-cancer Anti-microbial Beta-secretase 1 enzyme
Electronic supplementary material The online version of this article (doi:10.1007/s00044-013-0469-8) contains supplementary material, which is available to authorized users. G. Nelson M. A. Alam (&) T. Atkinson S. Gurrapu J. Sravan Kumar C. Bicknese J. L. Johnson M. Williams Department of Chemistry and Biochemistry, University of Minnesota Duluth, Duluth, MN 55812, USA e-mail: [email protected]
123
Introduction Chalcones of various classes have been extensively investigated for anti-proteasomal activity (Bazzaro et al., 2011; Achanta et al., 2006), anti-cancer activity (Kim et al., 2010; Dimmock et al., 1999; Echeverria et al., 2009; Go et al., 2005; Zhou et al., 2009), anti-microbial activity (Ahmad et al., 2011; Venkatesan and Maruthavanan, 2011; Choudhary et al., 2011; Liaras et al., 2011; Karamunge et al., 2011), and several other therapeutic uses (Jianzhang et al., 2011; Fei et al., 2011; Umair et al., 2011; Ramesh and Babitha, 2009). Very recently (Chiaradia et al., 2012) reported naphthaline derived chalcones as a potent inhibitor of Mycobacterium tuberculosis protein tyrosine phosphatase. Beta-secretase 1 or beta-site APP cleaving enzyme 1 (BACE1), the main cause of Alzheimer’s disease (AD) is an aspartic-acid protease encoded by BACE1 gene. AD is a neurodegenerative disease and the most common type of dementia. AD affects millions of elderly persons worldwide and is a major global social and financia
Data Loading...
