Synthesis, Cytotoxicity and Docking Simulation of Novel Annulated Dihydroisoquinoline Heterocycles.

doi:10.2174/1389557520666200130104632

Paper

Synthesis, Cytotoxicity and Docking Simulation of Novel Annulated Dihydroisoquinoline Heterocycles.

Published Jan 29, 2020 · Fatma M. Saleh, H. Hassaneen, Magda F. Mohamed

Mini reviews in medicinal chemistry

Q2 SJR score

1

Citations

0

Influential Citations

Full textSemantic Scholar

Abstract

Coupling of ethyl 2-(6,7-dimethoxy-3,4-dihydroisoquinolin-1-yl)acetate 2 with diazotized anilines in ethanol in the presence of sodium acetate yielded 2-(2-arylhydrazono)-2-(6,7-dimethoxy-3,4-dihydroisoquinolin-1-yl)acetate (4a-f). Treatment of 2 with α-bromoketones 6a-f in dry benzene at reflux gave the corresponding isoquinolinium bromides 7a-f. Refluxing of each of the latter salts 7a-f in dry benzene and in the presence of triethylamine yielded 2-arylpyrrolo-[2,1-a]isoquinoline structures 8a-f, that converted to ethyl (E)-8,9-dimethoxy-3-(phenyldiazen-yl)-2-(aryl)-5,6-dihydropyrrolo[2,1-a]isoquinoline-1-carboxylate (9a-f) upon treatment with diazotized anilines 3 in ethanol in the presence of sodium acetate. Cytotoxic assay was performed for in vitro antitumor screening against caucasian breast adenocarcinoma (MCF7), hepatocellular carcinoma (HepG2) and colorectal carcinoma (HCT-116) cell lines. The results were compared with the standard anticancer drug (doxorubicin). Molecular docking using MOE 2014.09 software was carried out for the most potent compound 4d which showed the highest binding affinity toward the four tested proteins and thus initiated apoptosis of cancer cells.

Study Snapshot

Novel annulated dihydroisoquinoline heterocycles show potential as potent anticancer drugs, initiating apoptosis in cancer cells when bound to specific proteins.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Sign up to use Study Snapshot

Consensus is limited without an account. Create an account or sign in to get more searches and use the Study Snapshot.

Create an account

Paper

Synthesis, Cytotoxicity and Docking Simulation of Novel Annulated Dihydroisoquinoline Heterocycles.

Sign up to use Study Snapshot

References

Citations

An efficient method based on an inhibitor-enzyme complex to screen an active compound against lipase from Toona sinensis.

The study developed a rapid method to screen lipase inhibitors from Toona sinensis, identifying 1,2,3,4,6-penta-O-galloyl--D-glucose as a promising compound for bioactive compounds in natural food and plants.