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Synthesis of Novel Tacrine Analogs as Acetylcholinesterase Inhibitors
Author(s) -
Mahdavi Mohammad,
Saeedi Mina,
Gholamnia Laleh,
Jeddi Seyed Amir Behzad,
Sabourian Reyhaneh,
Shafiee Abbas,
Foroumadi Alireza,
Akbarzadeh Tahmineh
Publication year - 2017
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.2594
Subject(s) - chemistry , tacrine , malononitrile , acetylcholinesterase , cyclohexanone , rivastigmine , butyrylcholinesterase , pyrazolones , aryl , stereochemistry , pyrazole , cholinesterase , combinatorial chemistry , medicinal chemistry , organic chemistry , aché , enzyme , pharmacology , catalysis , medicine , dementia , alkyl , disease , pathology , donepezil
In this work, a wide range of novel pyrazolo[4′,3′:5,6]pyrano[2,3‐ b ]quinolin‐5‐amines were synthesized as tacrine analogs. At first, reaction of 3‐methyl‐1‐phenyl‐1 H ‐pyrazol‐5(4 H )‐one, aromatic aldehydes, and malononitrile gave 6‐amino‐4‐aryl‐3‐methyl‐1‐phenyl‐1,4‐dihydropyrano[2,3‐ c ]pyrazole‐5‐carbonitriles. Then, reaction of the latter compounds with cyclohexanone led to the formation of the title compounds. Also, they were evaluated for their in vitro acetylcholinesterase and butyrylcholinesterase inhibitory activities. Interestingly, most of them showed good inhibitory activity comparing with rivastigmine as the reference drug.