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Microwave-Assisted Synthesis Of Condensed 1,4-Dihydropyridines As Potential Calcium Channel Modulators

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Date
2015
Author
Ozer, Erdem Kamil
Gunduz, Miyase Gozde
El-Khouly, Ahmed
Sara, Mehmet Yildirim
Simsek, Rahime
Iskit, Alper Bektas
Safak, Osman Cihat
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Abstract
This study reports the design, synthesis, and calcium channel modulatory activity evaluation of a series of 14 novel fused 1,4-dihydropyridine derivatives. The molecular design of the compounds was based on modifications of nifedipine, which is a calcium channel blocker. The compounds were achieved by one-pot microwave-assisted reaction of 4,4-dimethyl-1,3-cyclohexanedione, 5-chlorosalicylaldehyde/3,5-dichlorosalicylaldehyde, an appropriate alkyl acetoacetate, and ammonium acetate in ethanol according to a modified Hantzsch reaction. The structures of the compounds were confirmed by spectral methods and elemental analysis. To evaluate their relaxant activities, the maximum relaxant response (E-max) and pD(2) values of the compounds and nifedipine were determined on isolated rat aorta rings. The obtained results indicated that all compounds produced concentration-dependent relaxation on the rings possibly due to the blockade of calcium channels. The E-max values (a measure of efficacy) of five compounds were higher than those of nifedipine.
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https://doi.org/10.3906/kim-1412-72
http://hdl.handle.net/11655/20024
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