J. Guillon, David Montoir, M. Marchivie
Jul 10, 2017
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X-ray Structure Analysis Online
Abstract
Naphthyridones are well-known heterocyclic building-blocks that have been attracting considerable attention due to their potential pharmaceutical interests. Especially, 1,8-naphthyridin4(1H)-ones have been widely investigated as aza-heterocycles with a large family of fluoroquinolones antibiotics.1 Moreover, substituted 1,6-naphthyridin-2(1H)-one compounds have shown many interesting biological activities as, for example, cardiotonic drugs,2 protein kinases inhibitors3 or neuroprotective agents.4 Furthermore, due to this large range of biological applications we undertook to investigate the synthesis of functionalized 1,6-naphthyridin-2(1H)-ones5 in order to propose a practical access to these heterocycles and find potential biological activities. We report herein on the structural characterization of the N-(7{[2-(dimethylamino)ethyl]amino}-1-methyl-2-oxo-1,2-dihydro1,6-naphthyridin-3-yl)-3,4,5-trimethoxybenzamide (Fig. 1), a 1,6-naphthyridin-2(1H)-one derivative that has been described to display antiproliferative activity towards breast cancer cell lines.5 The title compound was synthesized by through regioselective palladium-catalyzed cross-coupling reactions. Pale-yellow crystals having dimensions of 0.24 × 0.13 × 0.04 mm3 suitable for X-ray diffraction analysis were obtained by the slow crystallization from a dichloromethane–ethyl acetate solution at +20°C. The molecular structure of the title compound is depicted in Fig. 2. Crystal and experimental data are given in Table 1. Crystallographic data of this compound were collected at 200 K with a Bruker APEX II diffractometer using monochromatic Mo-Kα radiation (λ = 0.71073 Å). The collected data were reduced using SAINT software (SAINT, Bruker AXS Inc., Madison, Wisconsin, USA), and all reflections were used for unit-cell refinement. The crystal structure was solved by direct methods and successive Fourier difference syntheses with the SHELXS program.6 Refinement of the crystal structure was performed on F2 by weighted anisotropic full-matrix leastsquares methods using the SHELXL program.6 An absorption correction was performed by semi-empirical methods using the 2017 © The Japan Society for Analytical Chemistry