New Derivatives of 9-Amino-1,2,3,4-tetrahydroacridine

Brian, W. P.; Souther, B. L.

doi:10.1021/jm00325a041

Cited by 9 publications

(6 citation statements)

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“…Compounds were synthesized by heating a mixture of 9‐chloro‐1,2,3,4‐tetrahydroacridine (10.9 g, 0.05 mol) and n ‐alkylamine (0.12 mol) in phenol (50 g) at 125–130°C for 5 h, [7]. Their identities were confirmed by spectroscopic methods.…”

Section: Methodsmentioning

confidence: 99%

Studies on a new series of THA analogues: Effects of the aromatic residues that line the gorge of AChE

et al. 1997

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A series of N-monoalkylsubstituted 1,2,3,4-tetrahydro-9-aminoacridines have been prepared after modelling simulation of the AChE-inhibitor complex. Molecular modelling has predicted a number of hydrophobic residues to be involved in the catalytic mechanism of this interaction between the binding sites of AChE and this series of aminoacridines. In these compounds the acridine moiety becomes sandwiched between the rings of PHE330 and TRP84. In particular, the alkyl chain shows the important role of aromatic groups as binding sites. Their in vitro inhibitory properties (enzyme from Electrophorus electricus) confirm the aromatic groups as a general and significant characteristic of the mechanism of AChE inhibition.

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Section: Methodsmentioning

confidence: 99%

Studies on a new series of THA analogues: Effects of the aromatic residues that line the gorge of AChE

et al. 1997

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“…Org. Chem., 30, 2225(1965. Abstr., 61, 8317c (1964)] refers to it as 2-amino-5-phenyl-l,3,4-oxadiazole hydrochloride.…”

mentioning

confidence: 99%

2-Amino-5-Substituted 1,3,4-Oxadiazoles and 5-Imino-2-Substituted Δ²-1,3,4-Oxadiazolines. A Group of Novel Muscle Relaxants

Yale¹,

Losee²

1966

J. Med. Chem.

140

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“…All the chemicals, reagents, and solvents were obtained from commercial vendors [Sigma‐Aldrich (St. Louis, MO, USA), Acros Organics (Waltham, MA, USA), and Alfa Aesar, Ward Hill, MA, USA] with ≥ 95% purity and were used without further purification. The tetrahydroacridin‐9‐amine derivatives 7a – c , 8a , 8d , 9a , and 10a are known compounds which were reported earlier . 1 H NMR spectra were obtained and analyzed using a 300‐MHz spectrometer (Bruker ® Avance; Department of Chemistry, University of Waterloo).…”

Section: Methodsmentioning

confidence: 78%

Structure–activity relationship studies of benzyl‐, phenethyl‐, and pyridyl‐substituted tetrahydroacridin‐9‐amines as multitargeting agents to treat Alzheimer's disease

et al. 2016

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A library of substituted tetrahydroacridin-9-amine derivatives were designed, synthesized, and evaluated as dual cholinesterase and amyloid aggregation inhibitors. Compound 8e (N-(3,4-dimethoxybenzyl)-1,2,3,4-tetrahydroacridin-9-amine) was identified as a potent inhibitor of butyrylcholinesterase (BuChE IC = 20 nm; AChE IC = 2.2 μm) and was able to inhibit amyloid aggregation (40% inhibition at 25 μm). Compounds 9e (6-chloro-N-(3,4-dimethoxybenzyl)-1,2,3,4-tetrahydroacridin-9-amine, AChE IC = 0.8 μm; BuChE IC = 1.4 μm; Aβ-aggregation inhibition = 75.7% inhibition at 25 μm) and 11b (6-chloro-N-(3,4-dimethoxyphenethyl)-1,2,3,4-tetrahydroacridin-9-amine, AChE IC = 0.6 μm; BuChE IC = 1.9 μm; Aβ-aggregation inhibition = 85.9% inhibition at 25 μm) were identified as the best compounds with dual cholinesterase and amyloid aggregation inhibition. The picolylamine-substituted compound 12c (6-chloro-N-(pyridin-2-ylmethyl)-1,2,3,4-tetrahydroacridin-9-amine) was the most potent AChE inhibitor (IC = 90 nm). These investigations demonstrate the utility of 3,4-dimethoxyphenyl substituent as a novel pharmacophore possessing dual cholinesterase inhibition and anti-Aβ-aggregation properties that can be used in the design and development of small molecules with multitargeting ability to treat Alzheimer's disease.

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New Derivatives of 9-Amino-1,2,3,4-tetrahydroacridine

Cited by 9 publications

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Studies on a new series of THA analogues: Effects of the aromatic residues that line the gorge of AChE

Studies on a new series of THA analogues: Effects of the aromatic residues that line the gorge of AChE

2-Amino-5-Substituted 1,3,4-Oxadiazoles and 5-Imino-2-Substituted Δ²-1,3,4-Oxadiazolines. A Group of Novel Muscle Relaxants

Structure–activity relationship studies of benzyl‐, phenethyl‐, and pyridyl‐substituted tetrahydroacridin‐9‐amines as multitargeting agents to treat Alzheimer's disease

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New Derivatives of 9-Amino-1,2,3,4-tetrahydroacridine

Cited by 9 publications

References 0 publications

Studies on a new series of THA analogues: Effects of the aromatic residues that line the gorge of AChE

Studies on a new series of THA analogues: Effects of the aromatic residues that line the gorge of AChE

2-Amino-5-Substituted 1,3,4-Oxadiazoles and 5-Imino-2-Substituted Δ2-1,3,4-Oxadiazolines. A Group of Novel Muscle Relaxants

Structure–activity relationship studies of benzyl‐, phenethyl‐, and pyridyl‐substituted tetrahydroacridin‐9‐amines as multitargeting agents to treat Alzheimer's disease

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Product

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2-Amino-5-Substituted 1,3,4-Oxadiazoles and 5-Imino-2-Substituted Δ²-1,3,4-Oxadiazolines. A Group of Novel Muscle Relaxants