SYNTHESIS, CYTOTOXICITY AND DOCKING SIMULATION OF BIOACTIVE [1,2,4] TRIAZOLO [3,4-a] DIHYDROISOQUINOLINE CHALCONE DERIVATIVES

1-(1-Aryl-8,9-dimethoxy-1,5,6,10b-tetrahydro-[1,2,4]triazolo[3,4-a]-isoquinolin-3-yl)ethan-l-ones 4 were prepared via reaction of C-acetylmethanohydrazonoyl chlorides 1A,B with 6,7-dimethoxy-3,4-dihydroisoquinoline 3. Treatment of the latter products 4 with 3-aryl-1-phenyl-1H-pyrazole-4-carbaldehyde...

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Published inHeterocycles Vol. 104; no. 2; pp. 339 - 351
Main Authors Hassaneen, Hamdi M., Teleb, Mohamed A. M., Hassan, Nourhan, Hassaneen, Huwaida M. E., Laboud, Yara N., Saleh, Fatma M.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 01.01.2022
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
INHIBITORY-ACTIVITIES
DESIGN
POTENT
ANTICANCER
PYRAZOLE DERIVATIVES
ANTIBACTERIAL ACTIVITY
ANALOGS
BIOLOGICAL EVALUATION
ANTIFUNGAL
ANTITUMOR
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Summary:1-(1-Aryl-8,9-dimethoxy-1,5,6,10b-tetrahydro-[1,2,4]triazolo[3,4-a]-isoquinolin-3-yl)ethan-l-ones 4 were prepared via reaction of C-acetylmethanohydrazonoyl chlorides 1A,B with 6,7-dimethoxy-3,4-dihydroisoquinoline 3. Treatment of the latter products 4 with 3-aryl-1-phenyl-1H-pyrazole-4-carbaldehyde derivatives 5 in ethanol in the presence of sodium hydroxide solution at room temperature afforded chalcones 6. Cytotoxic assay was performed for in vitro antitumor screening against caucasian breast adenocarcinoma (MCF7) and hepatocellular carcinoma (HepG2) cell lines. Chalcones 6Ab and 6Ba have promising cytotoxic effects against MCF7 with IC50 values 8.0 and 7.5 mu g/mL, respectively. Molecular docking using Mcule.com was carried out, for the most potent compounds 6Ab and 6Ba, against two protiens which are EGFR and DHFR.
ISSN:0385-5414
1881-0942
DOI:10.3987/COM-21-14579