Synthesis and Biological Evaluation of New Tricyclic Dihydropyridine Based Derivatives on Potassium Channels

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Gunduz Miyase Gozde; Kaya Yesim; simsek Rahime; Sahin Erdemli Inci; safak Cihat

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Journal Paper

Paper Information

Journal: Iranian Journal of Pharmaceutical Research Year:2016 | Volume:15 | Issue:4 Page(s): 763-775

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Title

Synthesis and Biological Evaluation of New Tricyclic Dihydropyridine Based Derivatives on Potassium Channels

Author(s)

Keywords

4-Dihydropyridine;

Potassium channel;

Pinacidil;

Docking

Abstract

The present study reports a microwave-assisted method for the synthesis of twelve novel tricyclic 1, 4-dihydropyridine derivatives in which dimethyl-substituted cyclohexane and / or tetrahydrothiophene rings are fused to the DHP ring. The structures of the compounds were confirmed by spectral methods and elemental analysis. The potassium channel opening effects of the compounds were determined on rat mesenteric arteries and urinary bladders. The obtained results indicated that some compounds produced mesenteric artery-selective relaxant properties and the effects of these compounds were mediated through ATP-sensitive potassium channels. The replacement of the second tetrahydrothiophene ring with dimethyl-substituted cyclohexane ring led to more active compounds. Docking studies were carried out to understand the interactions of the compounds with the active site of potassium channel. The unsubstituted nitrogen atom on the 1, 4-dihydropyridine ring and one of the sulfonyl oxygens were found to be important for the formation of hydrogen bonds to stabilize the compound in the center of the cavity. The nature and position of phenyl ring substituents were also effective on the activity of the compounds. Finally, a theoretical study was established to predict the ADME of the most active compounds.

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APA: Copy

Gunduz, Miyase Gozde, Kaya, Yesim, simsek, Rahime, Sahin Erdemli, Inci, & safak, Cihat. (2016). Synthesis and Biological Evaluation of New Tricyclic Dihydropyridine Based Derivatives on Potassium Channels. IRANIAN JOURNAL OF PHARMACEUTICAL RESEARCH (IJPR), 15(4), 763-775. SID. https://sid.ir/paper/289054/en

Vancouver: Copy

Gunduz Miyase Gozde, Kaya Yesim, simsek Rahime, Sahin Erdemli Inci, safak Cihat. Synthesis and Biological Evaluation of New Tricyclic Dihydropyridine Based Derivatives on Potassium Channels. IRANIAN JOURNAL OF PHARMACEUTICAL RESEARCH (IJPR)[Internet]. 2016;15(4):763-775. Available from: https://sid.ir/paper/289054/en

IEEE: Copy

Miyase Gozde Gunduz, Yesim Kaya, Rahime simsek, Inci Sahin Erdemli, and Cihat safak, “Synthesis and Biological Evaluation of New Tricyclic Dihydropyridine Based Derivatives on Potassium Channels,” IRANIAN JOURNAL OF PHARMACEUTICAL RESEARCH (IJPR), vol. 15, no. 4, pp. 763–775, 2016, [Online]. Available: https://sid.ir/paper/289054/en

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