Synthesis, structural characterization and myorelaxant activity of 4-naphthylhexahydroquinoline derivatives containing different ester groups

Miyase Gozde Gunduz, Emine Albayrak, Fatma Isli, Gokce Sevim Ozturk Fincan, Seniz Yildirim, Rahime Simsek, Cihat Safak, Yusuf Sarioglu, Sema Ozturk Yildirim, Ray J Butcher

Abstract


The present study reports the synthesis, structural characterization and myorelaxant activity evaluation of a series of 16 novel 4-naphthylhexa­hydroquinoline derivatives. The compounds were achieved by one-pot micro­wave-assisted method via a modified Hantzsch reaction. The structures of the compounds were confirmed by various spectral methods, such as IR, 1D and 2D NMR techniques and mass analysis. X-Ray studies of compound 10 pro­vided further evidence for the proposed structure. To evaluate their myorelax­ant activities, the Emax and pD2 values of the compounds and nifedipine were determined on isolated rabbit gastric fundus smooth muscle strips. The obtained results indicated that the introduction of long chain alkyl groups, such as the 2-methoxyethyl or 2-(methacryloyloxy)ethyl moiety, to the ester group led to the most active compounds. 


Keywords


1,4-dihydropyridine; synthesis; myorelaxant activity; crystal structure, structure elucidation

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DOI: https://doi.org/10.2298/JSC151206035G

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