Synthesis, Physico-Chemical Properties and DFT Calculations of New 2-(4- Arylpiperazine-1-yl)-1-(3-ethylbenzofuran-2-yl)ethanols As Potential Antihypertensive Agents

Author(s): Zuzana Mandelova, Radka Opatrilova, Ivan Raich, Jaroslav Havlicek, Sandra Kacerova, Tomas Pekarek, Marcela Tkadlecova, Petra Staskova, Jiri Dohnal, Jozef Csollei, Josef Jampilek

Journal Name: Current Organic Chemistry

Volume 15 , Issue 7 , 2011

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Abstract:

Six new arylpiperazinylbenzofurane derivatives as potential hybrid antihypertensive agents were designed and synthesised. The discussed compounds were prepared as free bases and subsequently they were transformed to hydrochloride salts. The position of protonation of nitrogen atoms in the piperazine ring in hydrochloride salts was determined by means of IR spectrometry and 13C CP/MAS and 15N CP/MAS NMR spectroscopy. Using these solid state analytical methods it was found that both nitrogen atoms were protonated. These results were supported by elemental analysis and also by ab initio/DFT calculations of partial charges and proton affinities. Physico- chemical properties of free bases and salts are discussed; especially partition and distributive coefficients log P and log D7.4, dissociation constants pKa and molecular surfaces and volumes. The experimental results were also subsequently correlated with ab initio/DFT calculations.

Keywords: Heteroarylethanolamines, Piperazine, CP/MAS NMR spectroscopy, IR spectrometry, Ab initio/DFT calculations, Physicochemical properties, hypertension, cardiovascular mortality, renal diseases, hypertrophy, β-blockers, Arylpiperazine substitution, chromatography, UV irradiation, titration

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Article Details

VOLUME: 15
ISSUE: 7
Year: 2011
Page: [1081 - 1096]
Pages: 16
DOI: 10.2174/138527211794785154
Price: $58

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