Synthesis, Antimicrobial and Antitumor Study of New Pyrido[2,1-a]isoquinolines via Isoquinoline-1-acetonitrile
- 1 January 2021
- journal article
- research article
- Published by The Japan Institute of Heterocyclic Chemistry in HETEROCYCLES
- Vol. 102 (9), 1729-1742
- https://doi.org/10.3987/com-21-14494
Abstract
Refluxing of enaminonitrile 3 with arylacetonitriles 2 in ethanol in the presence of piperidine afforded 4H-pyrido[2,1-a]isoquinoline-1-carbonitriles 6. Refluxing of 2-(6,7-dimethoxy-3,4-dihydroisoquinolin-1-yl)acetonitrile 1 with ethyl 3-aryl-2-cyanoacrylates 9 in acetonitrile in the presence of piperidine gave the corresponding 4H-pyrido[2,1-a]isoquinoline-1,3-dicarbonitriles 13. All the new synthesized compounds were identified by elemental analysis and spectral data. Cytotoxic assay was investigated for in vitro antitumor screening against MCF7, HepG2 and HCT-116 cell lines. Molecular docking using Mcule.com. software was carried out for the most potent compound 6b. The results are compared with doxorubicin standard anticancer drug. Antimicrobial activities were investigated, and all compounds revealed no antimicrobial activities against all tested strains except compounds 13b and 13e.Keywords
This publication has 31 references indexed in Scilit:
- Studies with Enamines: Route to Aminoazolopyrimidines and ArylazoazolopyrimidinesZeitschrift für Naturforschung B, 2013
- Wild-Type MIC Distribution and Epidemiological Cutoff Values for Aspergillus fumigatus and Three Triazoles as Determined by the Clinical and Laboratory Standards Institute Broth Microdilution MethodsJournal of Clinical Microbiology, 2009
- Selective Benzopyranone and Pyrimido[2,1-a]isoquinolin-4-one Inhibitors of DNA-Dependent Protein Kinase: Synthesis, Structure−Activity Studies, and Radiosensitization of a Human Tumor Cell Line in VitroJournal of Medicinal Chemistry, 2004
- Michael Reactions of Arylidenesulfonylacetonitriles. A New Route to Polyfunctional Benzo[a]quinolizinesMolecules, 2002
- Prediction of Hydrophobic (Lipophilic) Properties of Small Organic Molecules Using Fragmental Methods: An Analysis of ALOGP and CLOGP MethodsThe Journal of Physical Chemistry A, 1998
- Inhibition of Tubulin Polymerization by 5,6-Dihydroindolo[2,1-a]isoquinoline DerivativesJournal of Medicinal Chemistry, 1997
- N-(1,3,4,6,7,12b-hexahydro-2H-benzo[b]furo[2,3-a]quinolizin-2-yl)-N-methyl-2-hydroxyethanesulfonamide: a potent and selective .alpha.2-adrenoceptor antagonistJournal of Medicinal Chemistry, 1985
- The Emetine AlkaloidsJournal of Natural Products, 1984
- HL 725, an extremely potent inhibitor of platelet phosphodiesterase and induced platelet aggregation in vitroLife Sciences, 1982
- 973. The synthesis of emetine and related compounds. Part III. The reaction of some isoquinoline derivatives with acrylonitrileJournal of the Chemical Society, 1961