Synthesis, antihistaminic action and theoretical studies of (4-methoxybenzyl)(1,4,5,6-tetrahydropirimidin-2-yl)amine hydroiodide

Synthesis, antihistaminic action and theoretical studies of... In this study, (4-methoxybenzyl)(1,4,5,6-tetrahydropyrimidin-2-yl)amine hydroiodide (2) was synthesized by reaction of 2-methylmercapto-1,4,5,6-tetrahydropyrimidine hydroiodide (1) and 4-methoxybenzylamine. The synthesized compound was tested for its in vitro H1-antihistaminic activity on guinea pig trachea. A promising bronchorelaxant effect of 2 was observed in histamine-contracted guinea pig tracheal chain via H1 receptor antagonism. In addition, the molecular geometry and gauge including atomic orbital (GIAO) 1H chemical shift values of the title compound in the ground state were calculated using the density functional method (DFT/UB3LYP) and Hartree–Fock (HF) approach using 6–311G+(d), 6–311G+(d,p), LANL2DZ, DGDZVP, and DGDZVP2 basis sets and compared with the experimental data. According to the experimental and theoretical results, HF/6–311G+(d) showed a better fit to experimental values in evaluating 1H-nuclear magnetic resonance (NMR) chemical shift values. Theoretical studies supported our findings, revealing the N12 atom as the most nucleophilic. In addition, other structures of the compound such as the aromatic ring and OCH3 group increased this property. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Research on Chemical Intermediates Springer Journals

Synthesis, antihistaminic action and theoretical studies of (4-methoxybenzyl)(1,4,5,6-tetrahydropirimidin-2-yl)amine hydroiodide

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Publisher
Springer Journals
Copyright
Copyright © 2012 by Springer Science+Business Media B.V.
Subject
Chemistry; Catalysis; Physical Chemistry; Inorganic Chemistry
ISSN
0922-6168
eISSN
1568-5675
D.O.I.
10.1007/s11164-012-0813-5
Publisher site
See Article on Publisher Site

Abstract

In this study, (4-methoxybenzyl)(1,4,5,6-tetrahydropyrimidin-2-yl)amine hydroiodide (2) was synthesized by reaction of 2-methylmercapto-1,4,5,6-tetrahydropyrimidine hydroiodide (1) and 4-methoxybenzylamine. The synthesized compound was tested for its in vitro H1-antihistaminic activity on guinea pig trachea. A promising bronchorelaxant effect of 2 was observed in histamine-contracted guinea pig tracheal chain via H1 receptor antagonism. In addition, the molecular geometry and gauge including atomic orbital (GIAO) 1H chemical shift values of the title compound in the ground state were calculated using the density functional method (DFT/UB3LYP) and Hartree–Fock (HF) approach using 6–311G+(d), 6–311G+(d,p), LANL2DZ, DGDZVP, and DGDZVP2 basis sets and compared with the experimental data. According to the experimental and theoretical results, HF/6–311G+(d) showed a better fit to experimental values in evaluating 1H-nuclear magnetic resonance (NMR) chemical shift values. Theoretical studies supported our findings, revealing the N12 atom as the most nucleophilic. In addition, other structures of the compound such as the aromatic ring and OCH3 group increased this property.

Journal

Research on Chemical IntermediatesSpringer Journals

Published: Sep 29, 2012

References

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