54233-07-7Relevant academic research and scientific papers
Structure–activity relationship studies of benzyl-, phenethyl-, and pyridyl-substituted tetrahydroacridin-9-amines as multitargeting agents to treat Alzheimer's disease
Osman, Wesseem,Mohamed, Tarek,Sit, Victor Munsing,Vasefi, Maryam S.,Beazely, Michael A.,Rao, Praveen P. N.
, p. 710 - 723 (2016/10/25)
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 IC50?=?20?nm; AChE IC50?=?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 IC50?=?0.8?μm; BuChE IC50?=?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 IC50?=?0.6?μm; BuChE IC50?=?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 (IC50?=?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.
Buchwald-Hartwig amination approach for the synthesis of functionalized 1,2,3,4-tetrahydroacridine derivatives
De Sousa, Julien,Brown, Richard C. D.,Baati, Rachid
, p. 3468 - 3474 (2014/06/09)
Electrophilic 1,2,3,4-tetrahydroacridin-9-yl trifluoromethanesulfonates have been prepared and applied for the first time in the synthesis of functionalized tacrines with high efficacy by using the Buchwald-Hartwig amination reaction. Remarkably, secondar
Search of antitubercular activities in tetrahydroacridines: Synthesis and biological evaluation
Tripathi,Verma,Pandey, Jyoti,Agarwal,Chaturvedi, Vinita,Manju,Srivastva,Gaikwad,Sinha
, p. 5144 - 5147 (2007/10/03)
A series of 9-substituted tetrahydroacridines were synthesized by nucleophilic substitution of chloro group with different nucleophiles in 9-chlorotetrahydroacridine (2). The latter could be obtained by POCl3 mediated cyclization of the interme
