Anticoccidial 1-substituted 4(1H)-pyridinone hydrazones

Douglas, Alan W.; Fisher, M. H.; Fishinger, J. J.; Gund, Peter; Harris, Elbert E.; Olson, G.; Patchett, A. A.; Ruyle, W. V.

doi:10.1021/jm00217a015

Cited by 18 publications

(8 citation statements)

References 10 publications

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“…In both cases, points for acyclic alcohols fall close to straight lines, eqs. (13) and (14). The highest deviations are for 2-propanol: 0.65 kJ/mol (1.4%) in L, 9 J/cm3 (1.6%) in S2.…”

Section: Surface Areasmentioning

confidence: 94%

Molecular mechanics and molecular shape. III. Surface area and cross‐sectional areas of organic molecules

Meyer

1986

J Comput Chem

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A nonanalytical procedure is proposed to calculate the surface area and cross-sectional areas of molecules. Results are reviewed for about 70 species comprising alkanes, acyclic and cyclic, alkyl halides, and alcohols. By regression analysis, relationships are detected between surface areas or segment areas and physical properties. Computed cross-sectional areas are confronted with adsorption values. Four ways are proposed to define quantitatively the intuitive notion of «molecular globularity».

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“…In both cases, points for acyclic alcohols fall close to straight lines, eqs. (13) and (14). The highest deviations are for 2-propanol: 0.65 kJ/mol (1.4%) in L, 9 J/cm3 (1.6%) in S2.…”

Section: Surface Areasmentioning

confidence: 94%

Molecular mechanics and molecular shape. III. Surface area and cross‐sectional areas of organic molecules

Meyer

1986

J Comput Chem

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“…Chemistry The synthesis of arylidenehydrazinylpyridinium derivatives was carried out according to the literature 22,23) as summarized in Chart 1. In the first step, 4-hydrazinylpyridine was obtained by nucleophilic substitution of hydrazine with 4-chloropyridine then corresponding hydrazone derivatives 1-3 were furnished by the condensation of 4-hydrazi-nylpyridine with aromatic ketones in ethanol under reflux.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, Biological Evaluation and Molecular Docking Study of Hydrazone-Containing Pyridinium Salts as Cholinesterase Inhibitors

Parlar

Bayraktar

Tarikogullari

et al. 2016

CHEMICAL & PHARMACEUTICAL BULLETIN

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A series of pyridinium salts bearing alkylphenyl groups at 1 position and hydrazone structure at 4 position of the pyridinium ring were synthesized and evaluated for the inhibition of both acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) enzymes. The cholinesterase (ChE) inhibitory activity studies were carried out by using the Ellman's colorimetric method. All compounds displayed considerable AChE and BuChE inhibitory activity and some of the compounds manifested remarkable anti-AChE activity compared to the reference compound, galantamine. Among the title compounds, the series including benzofuran aromatic ring exhibited the best inhibitory activity both on AChE and BuChE enzymes. Key words acetylcholinesterase inhibitor; butyrylcholinesterase inhibitor; docking study; pyridinium salt; hydrazone Acetylcholinesterase (AChE) is an enzyme which is responsible for the hydrolysis of acetylcholine (ACh).1) AChE inhibitors bind to the enzyme thereby increases the level of acetylcholine by inhibiting the hydrolysis of ACh to choline and acetate.2) AChE inhibitors are used as therapeutic agents in the treatment of disorders related to ACh diminution such as Alzheimer disease, myasthenia gravis, glaucoma.3) AChE has a deep, narrow gorge approximately 20 Å long. Catalytic active site (CAS) of the enzyme is located at the bottom of the gorge whereas peripheral anionic site (PAS) is at the entrance. 4) Although anti-AChE drugs show a wide range of chemical diversity, they generally include aromatic-heterocyclic ring systems and a nitrogen atom as chemical structure (Fig. 1). These structures have an important role for the interaction with specific amino acids in the enzyme.5) Aromaticheterocyclic nuclei generally have potential hydrophobic and charge-transfer interaction, while nitrogen atom and its quaternary form can make hydrogen or ionic bonds as well as dipole-dipole or ion-dipole interactions with amino acids in the enzyme gorge.5-10) In addition, quaternary nitrogen cation displays highly positive binding stabilization due to cation-π interactions with amino acid residues in AChE enzyme. [9][10][11][12] Many reports indicated that compounds bearing aromatic/ heteroaromatic rings on lateral parts of pyridinium displayed high AChE inhibitory activity and act as dual binding inhibitors. [13][14][15][16] According to the docking studies of these compounds, it was found that both terminal rings attached to the pyridinium were able to bind simultaneously to both CAS and PAS of the enzyme resulting in higher AChE inhibitory activity. [13][14][15][16] Among the reported studies, pyridinium derivatives having benzofuran ring were shown to have a significant AChE inhibitory activity and it was observed that benzofuran and phenyl moieties as terminal rings were interacted with both PAS and CAS of AChE. 15,16) On the other hand, many of compounds bearing hydrazonehydrazide functional group have been reported to possess ChE inhibitory activity. 17,18) The hydrazones have hydrogen donor and acceptor nitrogen atoms an...

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“…For the synthesis and pharmacological activity of (benzylidene-hydrazono)-1,4-dihydropyridine derivatives, see: Douglas et al (1977); Alptü zü n et al H atoms treated by a mixture of independent and constrained refinement Á max = 0.16 e Å À3 Á min = À0.18 e Å À3 Table 1 Hydrogen-bond geometry (Å , ). Symmetry codes: (i) x þ 1; y; z; (ii) x; Ày þ 3 2 ; z þ 1 2 ; (iii) Àx; Ày þ 1; Àz.…”

Section: Related Literaturementioning

confidence: 99%

Ethyl 2-{3-[(2-chloro-1,3-thiazol-5-yl)methyl]-4-nitroimino-1,3,5-triazinan-1-yl}acetate

et al. 2010

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In the title compound, C11H15ClN6O4S, which belongs to the neonicotinoid class of insecticidally active heterocyclic compounds, the six-membered triazine ring adopts an opened envolope conformation. The planar nitro imine group [dihedral angle between nitro and imine groups = 1.07 (7)°] and the thiazole ring are oriented at a dihedral angle of 69.62 (8)°. A classical intramolecular N—H⋯O hydrogen bond is found in the molecular structure. Moreover, one classical intermolecular N—H⋯N and four non-classical C—H⋯O and C—H⋯N hydrogen bonds are also present in the crystal structure. Besides intermolecular hydrogen bonds, the Cl atom forms an intermolecular short contact [3.020 (2) Å] with one of the nitro O atoms.

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Anticoccidial 1-substituted 4(1H)-pyridinone hydrazones

Cited by 18 publications

References 10 publications

Molecular mechanics and molecular shape. III. Surface area and cross‐sectional areas of organic molecules

Molecular mechanics and molecular shape. III. Surface area and cross‐sectional areas of organic molecules

Synthesis, Biological Evaluation and Molecular Docking Study of Hydrazone-Containing Pyridinium Salts as Cholinesterase Inhibitors

Ethyl 2-{3-[(2-chloro-1,3-thiazol-5-yl)methyl]-4-nitroimino-1,3,5-triazinan-1-yl}acetate

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