Novel anthelmintic agents. II. Pyrantel and other cyclic amidines

McFarland, James W.; Conover, L. H.; Howes, Harold L.; Lynch, John E.; Chisholm, D. R.; Austin, W. C.; Cornwell, R.L.; Danilewicz, John C.; Courtney, Welby G.; Morgan, Delmar

doi:10.1021/jm00306a023

Cited by 49 publications

(11 citation statements)

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“…Beyond the chemical and biochemical interest of 4,5‐1 H ‐dihydroimidazole, the synthesis as well as vibrational and structural studies are of pharmacological importance because some substances of this kind present antihypertensive, antihelminthic, hypoglycemic, anti‐inflammatory, and analgesic activities 1–6. These biological effects were attributed to the activation of three groups of imidazoline receptors 7.…”

Section: Introductionmentioning

confidence: 99%

Structural and vibrational study of 2‐(2′‐ furyl)‐4,5‐1H‐dihydroimidazole

Zinczuk

Ledesma

Brandán

et al. 2009

J of Physical Organic Chem

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In this study 2-(2(-furyl)-4,5-1H-dihydroimidazole (1) was prepared and then characterized by infrared, Raman, and multidimensional nuclear magnetic resonance (NMR) spectroscopies. The crystal and molecular structures of 1 were determined by X-ray diffraction methods. The density functional theory (DFT) and second-order Møller-Plesset theory (MP2) with Pople's basis set show that there are two conformers for the title molecule that have been theoretically determined in the gas phase, and that only one of them, conformer I, is present in the solid phase. NMR spectra observed for 1 were successfully compared with the calculated chemical shifts at the B3LYP/6-311RRG ** level theorized for this conformer. The harmonic vibrational frequencies for the optimized geometry of the latter conformer were calculated at the B3LYP/6-311RRG ** level in the approximation of the isolated molecule. For a complete assignment of the IR and Raman spectra in the solid phase of 1, DFT calculations were combined with Pulaý s scaled quantum mechanics force field (SQMFF) methodology to fit the theoretical frequency values to the experimental ones.

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Section: Introductionmentioning

confidence: 99%

Structural and vibrational study of 2‐(2′‐ furyl)‐4,5‐1H‐dihydroimidazole

Zinczuk

Ledesma

Brandán

et al. 2009

J of Physical Organic Chem

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“…1 H -4,5-Dihydroimidazoles (2-imidazolines, I ) are cyclic amidines of pharmacological interest owing to certain properties exhibited by some members of the class, such as antihypertensive [ 1 ], antihelminthic [ 2 , 3 ], hypoglycemic [ 5 ], antiinflamatory and analgesic activity [ 4 ]. These biological effects were attributed to activation of three groups of imidazoline receptors (I 1 , I 2 , I 3 ) [ 6 ].…”

Section: Introductionmentioning

confidence: 99%

1H- and 13C-NMR Analysis of a Series of 1,2-Diaryl-1H-4,5-dihydroimidazoles

Salerno¹,

Perillo²

2005

Molecules

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An analysis of the 1H- and 13C-NMR spectra of a series of 1,2-diaryl-1H-4,5-dihydroimidazoles and comparisons with 4,5-dihydroimidazoles having different substitution patterns are presented. The influence of different 1-aryl and 2-aryl group substituents on spectroscopic parameters of the heterocyclic ring and on the contributions of possible mesomeric structures in the system was determined. Spectroscopic features are coherent with the presence of two conjugated systems (Ar1-N and Ar2-C=N) which compete with the delocalization characteristics of the amidine system.

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“…Optimal activity against a variety of nematodes was obtained by enlarging the imidazoline to a tetrahydropyrimidine ring, as in pyrantel. 99 This was an orally active broad-spectrum anthelmintic that was effective against roundworms, hookworms and threadworms in both humans and animals.…”

Section: Pyrantelmentioning

confidence: 99%

Drugs Originating from the Screening of Organic Chemicals

Sneader

2005

Drug Discovery

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Novel anthelmintic agents. II. Pyrantel and other cyclic amidines

Cited by 49 publications

References 1 publication

Structural and vibrational study of 2‐(2′‐ furyl)‐4,5‐1H‐dihydroimidazole

Structural and vibrational study of 2‐(2′‐ furyl)‐4,5‐1H‐dihydroimidazole

1H- and 13C-NMR Analysis of a Series of 1,2-Diaryl-1H-4,5-dihydroimidazoles

Drugs Originating from the Screening of Organic Chemicals

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