Abstract
The title compounds C17H14BrNO2, (I), and C17H15NO3, (II), were obtained from the reaction of 6-meth-oxy-3,4-di-hydro-2H-naphthalen-1-one and 2-bromo-nicotinaldehyde in ethanol. Compound (I) was the expected product and compound (II) was the oxidation product from air exposure. In the crystal structure of compound (I), there are no short contacts or hydrogen bonds. The structure does display π-π inter-actions between adjacent benzene rings and adjacent pyridyl rings. Compound (II) contains two independent mol-ecules, A and B, in the asymmetric unit; both are non-planar, the dihedral angles between the meth-oxy-benzene and 1H-pyridin-2-one mean planes being 35.07 (9)° in A and 35.28 (9)°in B. In each mol-ecule, the 1H-pyridin-2-one unit participates in inter-molecular N-H⋯O hydrogen bonding to another mol-ecule of the same type (A to A or B to B). The structure also displays π-π inter-actions between the pyridyl and the benzene rings of non-equivalent mol-ecules (viz., A to B and B to A).
Highlights
B, in the asymmetric unit; both are non-planar, the dihedral angles between the methoxybenzene and 1H-pyridin-2-one mean planes being 35.07 (9) in A
The 1H-pyridin-2-one unit participates in intermolecular N—H O hydrogen bonding to another molecule of the same type (A to A or B to B)
Bioactive defense molecules found in plants and used in traditional Chinese medicine, have demonstrated anticancer, antibacterial, antifungal, and anti-inflammatory properties (Nowakowska, 2007; Katsori et al, 2011)
Summary
Our research strategy to synthesize novel compounds considered analogs of the natural product chalcone, which contains two aromatic rings and an --unsaturated ketone. Bioactive defense molecules found in plants and used in traditional Chinese medicine, have demonstrated anticancer, antibacterial, antifungal, and anti-inflammatory properties (Nowakowska, 2007; Katsori et al, 2011). Chalcones that contain methoxy groups (Shenvi et al, 2013; Bandgar et al, 2010) and/or pyridine groups (Prasad et al., 2008; Yee et al, 2005) have demonstrated activity against a variety of cancer cell lines and antibiotic-resistant bacteria. During the synthesis of the title compound (I) by the Claisen–Schmidt condensation of. The title compound (I) is a chalcone analog of one currently being studied for its potential anticancer and antibacterial activity [unpublished results]. Pyridyl angle being 36.18 (10) in A and 35.91 (10) in B
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