Synthesis and evaluation of new 1,2,3,4-tetrahydroisoquinoline analogs as antiglioma agents

Medicinal Chemistry Research
2011.0

Abstract

Novel tetrahydroisoquinoline (THI) analogs were designed, synthesized, and their antiglioma activity was evaluated. The results showed that 6,8-dimethoxy-1-(20 methoxybiphenyl-4-ylmethyl)-1,2,3,4-tetrahydroisoquinoline hydrochloride (25) demonstrated improved potency, and selectivity on C6 rat glioma vs cultured rat astrocytes (EC50 0.63 lM vs. 10.85 lM) compared to our recent lead molecule EDL-155 (EC50 1.5 lM vs. 27.4 lM). The isomers of 25 were isolated using a semi-preparative high-performance liquid chromatography (HPLC) method, and their in vitro biological evaluation revealed that (?) 25 was the most active, and it was nearly 21 fold more potent than (-) 25, suggesting the antiglioma profile is influenced by stereochemical factors.

Knowledge Graph

Similar Paper

Synthesis and evaluation of new 1,2,3,4-tetrahydroisoquinoline analogs as antiglioma agents
Medicinal Chemistry Research 2011.0
Discovery of Antiglioma Activity of Biaryl 1,2,3,4-Tetrahydroisoquinoline Derivatives and Conformationally Flexible Analogues
Journal of Medicinal Chemistry 2006.0
Design, Synthesis and Biological Evaluation of the Novel Antitumor Agent 2-benzyl-3, 4-dihydroisoquinolin-1(2H)-one and Its Derivatives
Lecture Notes in Electrical Engineering 2014.0
Substituted tetrahydroisoquinolines: synthesis, characterization, antitumor activity and other biological properties
European Journal of Medicinal Chemistry 2018.0
Design, synthesis and biological evaluation of novel 5-hydroxy-2-methyl-4H-pyran-4-one derivatives as antiglioma agents
MedChemComm 2018.0
Design, synthesis and biological evaluations of chirally pure 1,2,3,4-tertrahydroisoquinoline analogs as anti-cancer agents
European Journal of Medicinal Chemistry 2015.0
Synthesis and Pharmacological Evaluation of Noscapine-Inspired 5-Substituted Tetrahydroisoquinolines as Cytotoxic Agents
Journal of Medicinal Chemistry 2018.0
Thiazolidin-4-ones from 4-(methylthio)benzaldehyde and 4-(methylsulfonyl)benzaldehyde: Synthesis, antiglioma activity and cytotoxicity
European Journal of Medicinal Chemistry 2016.0
1-Aryl-tetrahydroisoquinoline analogs as active anti-HIV agents in vitro
Bioorganic & Medicinal Chemistry Letters 2008.0
Nonclassical antifolates, part 5. Benzodiazepine analogs as a new class of DHFR inhibitors: Synthesis, antitumor testing and molecular modeling study
European Journal of Medicinal Chemistry 2014.0