Publication: Design, synthesis and molecular docking studies of novel N-benzenesulfonyl-1,2,3,4-tetrahydroisoquinoline-based triazoles with potential anticancer activity
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Issued Date
2014
Resource Type
File Type
application/pdf
ISSN
2235234
Other identifier(s)
2-s2.0-84900986993
Rights Holder(s)
Scopus
Bibliographic Citation
European Journal of Medicinal Chemistry. Vol 81, (2014), p.192-203
Suggested Citation
Pingaew R., Mandi P., Nantasenamat C., Prachayasittikul S., Ruchirawat S., Prachayasittikul V. Design, synthesis and molecular docking studies of novel N-benzenesulfonyl-1,2,3,4-tetrahydroisoquinoline-based triazoles with potential anticancer activity. European Journal of Medicinal Chemistry. Vol 81, (2014), p.192-203. doi:10.1016/j.ejmech.2014.05.019 Retrieved from: https://hdl.handle.net/20.500.14740/6646
Abstract
A novel series of N-benzenesulfonyl-1,2,3,4-tetrahydroisoquinolines (14-33) containing triazole moiety were designed and synthesized through rational cycloadditions using the modified Pictet-Spengler reaction and the Click chemistry. Antiproliferative activity against four cancer cell lines (e.g., HuCCA-1, HepG2, A549 and MOLT-3) revealed that many substituted triazole analogs of benzoates (20, 29) and benzaldehydes (30, 32) exhibited anticancer activity against all of the tested cancer cell lines in which the ester analog 20 was shown to be the most potent compound against HuCCA-1 (IC50 = 0.63 μM) and A549 (IC50 = 0.57 μM) cell lines. Triazoles bearing phenyl (15, 24), tolyl (26, 27), acetophenone (19), benzoate (20, 29), benzaldehyde (21, 30) and naphthalenyl (25) substituents showed stronger anticancer activity against HepG2 cells than that of the etoposide. Interestingly, the p-tolyl analog (27) displayed the most potent inhibitory activity (IC50 = 0.56 μM) against HepG2 cells without affecting normal cells. Of the investigated tetrahydroisoquinoline-triazoles, the promising compounds 20 and 27 were selected for molecular docking against AKR1C3, which was identified to be a plausible target site. © 2014 Elsevier Masson SAS. All rights reserved.
Subject(s)
Acetophenone
Benzaldehyde
Benzoic acid
Ester
Naphthalene
Tetrahydroisoquinoline
Triazole derivative
Unclassified drug
Antineoplastic agent
Isoquinoline derivative
Triazole derivative
Animal cell
Antineoplastic activity
Antiproliferative activity
Article
Cancer cell line
Click chemistry
Controlled study
Cycloaddition
Cytotoxicity
Drug design
Drug structure
Drug synthesis
HepG2 cell line
IC 50
Molecular docking
Nonhuman
Pictet Spengler reaction
Substitution reaction
Animal
Cell proliferation
Chemical structure
Chemistry
Chlorocebus aethiops
Dose response
Drug design
Drug effects
Drug screening
Human
Structure activity relation
Synthesis
Tumor cell line
Vero cell line
Animals
Antineoplastic Agents
Cell Line, Tumor
Cell Proliferation
Cercopithecus aethiops
Dose-Response Relationship, Drug
Drug Design
Drug Screening Assays, Antitumor
Hep G2 Cells
Humans
Isoquinolines
Molecular Docking Simulation
Molecular Structure
Structure-Activity Relationship
Triazoles
Vero Cells
Benzaldehyde
Benzoic acid
Ester
Naphthalene
Tetrahydroisoquinoline
Triazole derivative
Unclassified drug
Antineoplastic agent
Isoquinoline derivative
Triazole derivative
Animal cell
Antineoplastic activity
Antiproliferative activity
Article
Cancer cell line
Click chemistry
Controlled study
Cycloaddition
Cytotoxicity
Drug design
Drug structure
Drug synthesis
HepG2 cell line
IC 50
Molecular docking
Nonhuman
Pictet Spengler reaction
Substitution reaction
Animal
Cell proliferation
Chemical structure
Chemistry
Chlorocebus aethiops
Dose response
Drug design
Drug effects
Drug screening
Human
Structure activity relation
Synthesis
Tumor cell line
Vero cell line
Animals
Antineoplastic Agents
Cell Line, Tumor
Cell Proliferation
Cercopithecus aethiops
Dose-Response Relationship, Drug
Drug Design
Drug Screening Assays, Antitumor
Hep G2 Cells
Humans
Isoquinolines
Molecular Docking Simulation
Molecular Structure
Structure-Activity Relationship
Triazoles
Vero Cells