9H‐Carbazole Derivatives Containing the N‐Benzyl‐1, 2, 3‐triazole Moiety as New Acetylcholinesterase Inhibitors. Issue 5 (27th March 2015)

• Record Type: Journal Article
• Authors: Akrami, Hamidreza; Mirjalili, Bibi F.; Khoobi, Mehdi; Moradi, Alireza; Nadri, Hamid; Emami, Saeed; Foroumadi, Alireza; Vosooghi, Mohsen; Shafiee, Abbas
• Is Part Of: Archiv der Pharmazie. Volume 348:Issue 5(2015:May)
• Page Start: 366
• Page End: 374
• Publication Date: 2015-03-27
• Subjects: Pharmaceutical chemistry -- Periodicals; Pharmacology -- Periodicals; 615.19
• DOI: 10.1002/ardp.201400365
• Languages: English
• ISSNs: 0365-6233

Abstract

<abstract abstract-type="main" xml:lang="en"> <title> <x xml:space="preserve">Abstract</x> </title> <sec id="ardp201400365-sec-0001" sec-type="section"> <p>A series of triazole‐containing carbazole derivatives were designed as new anti‐acetylcholinesterase (AChE) agents. The target compounds <bold>6a–q</bold> were simply prepared via a one‐pot three‐component click reaction of <italic>N</italic>‐propargyl‐9<italic>H</italic>‐carbazole, sodium azide, and an appropriate benzyl halide. The <italic>in vitro</italic> anti‐cholinesterase assay showed that the unsubstituted benzyl derivative <bold>6p</bold> along with the 2‐F, 2‐Me, 3‐Me, 3‐MeO, and 3‐F analogs (<bold>6a</bold>, <bold>6c</bold>, and <bold>6g–i</bold>) had significant anti‐AChE activity (IC₅₀s ≤ 3.8 μM). Among them, the 2‐methylbenzyl derivative <bold>6c</bold> with an IC₅₀ value of 1.9 μM was the most active compound. The SAR studies revealed that small halogen atoms such as the fluorine atom or electron‐donating groups such as methyl or methoxy at the <italic>ortho</italic> or <italic>meta</italic> positions of the benzyl pendent group could be tolerated or improved the anti‐AChE activity.</p> </sec> </abstract>