Synthesis, characterization and crystal structure of the 2-quinolone derivative

Abstract

2-Quinolones represent important structural motifs in the numerous biologically active compounds and naturally occurring alkaloids. Their derivatives show remarkable diversity of pharmalogical properties such as antibacterial, antifungal, anticancer, antitubercular, anti-inflammatory, and antihypertensive and play a significant role in the development of the new pharmaceuticals. On the other hand, propanoic acid derivatives are known for their uniqe terapeutic activity. In an effort to merge these two structural motifs, two-step synthesis of 3-(4-methyl-2-oxoquinolinyl)propanoic acid, 1, was performed. The obtained compound was characterized by melting point, FTIR and NMR spectra. The single crystals of molecule 1, was prepared by slow evaporation from the ethyl acetate solution. The single crystal X-ray analysis revealed that molecule 1 crystallizes in monoclinic P21/c space group with Z = 4. The main structural feature is pseudo wavy layer formed by O–H···O and C–H···O interactions between adjacent molecules, whereas among the layers π···π stacking and C–H···π interactions were observed, resulting in the formation of supramolecular network. The main crystallographic data for 1: C13H13NO3, a = 9.2414(4), b = 9.0128(3), c = 13.6567(6) Å, β = 109.676(4) °, V = 1071.06(8) Å 3 . The refinement based on F 2 (156 parameters) yielded: R1 = 0.0456, wR2 = 0.1287, S = 1.068 for all data, and R1 = 0.0433 for 1765 reflections with I ≥ 2σ(I).