A series of triazole-containing carbazole derivatives were designed as new anti-acetylcholinesterase (AChE) agents. The target compounds 6a-q were simply prepared via a one-pot three-component click reaction of N-propargyl-9H-carbazole, sodium azide, and an appropriate benzyl halide. The in vitro anti-cholinesterase assay showed that the unsubstituted benzyl derivative 6p along with the 2-F, 2-Me, 3-Me, 3-MeO, and 3-F analogs (6a, 6c, and 6g-i) had significant anti-AChE activity (IC50s ≤ 3.8 μM). Among them, the 2-methylbenzyl derivative 6c 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 ortho or meta positions of the benzyl pendent group could be tolerated or improved the anti-AChE activity.
Background:Chromene and anilinopyrimidine heterocyclics are attractive anticancer
compounds that have inspired many researchers to design novel derivatives bearing improved anticancer
activity.Methods:A series of pyrimidine-fused benzo[f]chromene derivatives 6a-x were synthesized as
anticancer hybrids of 1H-benzo[f]chromenes and anilinopyrimidines. The inhibitory activity of the
synthesized compounds 6a-x against cell viability of human chronic myelogenous leukemia
(K562), human acute lymphoblastic leukemia (MOLT-4) and human breast adenocarcinoma
(MCF-7) cell lines was evaluated using MTT assay. The interaction of the most promising compound
with calf-thymus DNA was also studied using spectrometric titrations and Circular Dichroism
(CD) spectroscopy.Results:Most compounds showed promising activity against tested cell lines. Among them, 2,4-
dimethoxyanilino derivative 6g exhibited the best profile of activity against tested cell lines
(IC50s = 1.6-6.1 μM) with no toxicity against NIH3T3 normal cell (IC50 >200 μM). The spectrometric
studies exhibited that compound 6g binds to DNA strongly and may change DNA conformation
significantly, presumably via a groove binding mechanism.Conclusion:The results of this study suggest that the prototype compound 6g can be considered as
a novel lead compound for the design and discovery of novel anticancer agents.
A series of 7H-benzo[7,8]chromeno[2,3-d]pyrimidin-8-amines 6a-t were synthesized as new potential antiproliferative agents. The in vitro antiproliferative activity evaluation of title compounds using MTT assay revealed that most compounds showed significant activity against tested cancer cell lines (A549, MOLT-4, and HeLa). The 2-fluoro-aniline derivatives 6e and 6l were the most active compounds against A549 and MOLT-4 cells, respectively. The benzylamine analog 6h showed superior activity against HeLa cells. However, compound 6l with IC values of 5.2-6.9 μM had the best profile of activity against all tested cell lines. The morphological and flow cytometric analyses showed that compound 6l can induce apoptosis in the MOLT-4 cells.
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