Synthesis and biological evaluation of some tacrine analogs: study of the effect of the chloro substituent on the acetylcholinesterase inhibitory activity

New tetrahydroquinoline derivatives were synthesized, characterized, and evaluated for their in vitro and in vivo acetylcholinesterase inhibitory activity as well as hepatotoxicity using tacrine as a reference standard. The obtained results revealed that most of the compounds comprising a chloro sub...

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Bibliographic Details
Published inMonatshefte für Chemie Vol. 147; no. 3; pp. 539 - 552
Main Authors Ragab, Hanan M., Ashour, Hayam M. A., Galal, Amal, Ghoneim, Asser I., Haidar, Hassan R.
Format Journal Article
LanguageEnglish
Published Vienna Springer Vienna 01.03.2016
Springer Nature
Subjects
Analytical Chemistry
Chemistry
Chemistry and Materials Science
Chemistry, Multidisciplinary
Chemistry/Food Science
Inorganic Chemistry
Organic Chemistry
Original Paper
Physical Chemistry
Physical Sciences
Science & Technology
Theoretical and Computational Chemistry
Chlorinated analogs
Bioorganic synthesis
Alzheimer’s disease
Tacrine
Acetylcholinesterase inhibitory activity
TARGET
ALZHEIMERS-DISEASE
DRUGS
HYPOTHESIS
HIGHLY POTENT
Alzheimer's disease
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Summary:New tetrahydroquinoline derivatives were synthesized, characterized, and evaluated for their in vitro and in vivo acetylcholinesterase inhibitory activity as well as hepatotoxicity using tacrine as a reference standard. The obtained results revealed that most of the compounds comprising a chloro substituent displayed higher activity when compared with the other analogs. Among the newly synthesized compounds, four analogs displayed in vitro and in vivo acetylcholinesterase inhibitory activity comparable to or slightly higher than tacrine. Among these compounds, the 2-chlorotetrahydroquinoline derivative emerged with hepatotoxicity results comparable to saline. Graphical abstract
ISSN:0026-9247
1434-4475
DOI:10.1007/s00706-015-1641-2