Please use this identifier to cite or link to this item: http://ir.swu.ac.th/jspui/handle/123456789/12238
Title: Novel triazole-tetrahydroisoquinoline hybrids as human aromatase inhibitors
Authors: Chamduang C.
Pingaew R.
Prachayasittikul V.
Prachayasittikul S.
Ruchirawat S.
Prachayasittikul V.
Keywords: 2 [[3 [4 (4 bromophenoxy) 1h 1,2,3 triazol 1 yl]phenyl]sulfonyl] 6,7 dimethoxy 1,2,3,4 tetrahydroisoquinoline
2 [[3 [4 [(4 benzylphenoxy)methyl] 1h 1,2,3 triazol 1 yl]phenyl]sulfonyl] 6,7 dimethoxy 1,2,3,4 tetrahydroisoquinoline
2 [[3 [4 [(4 bromophenoxy)methyl] 1h 1,2,3 triazol 1 yl]phenyl]sulfonyl] 6,7 dimethoxy 1,2,3,4 tetrahydroisoquinoline
2 [[3 [4 [[(1,1' biphenyl) 4 yloxy]methyl] 1h 1,2,3 triazol 1 yl]phenyl]sulfonyl] 6,7 dimethoxy 1,2,3,4 tetrahydroisoquinoline
6,7 dimethoxy 2 [[3 [4 (phenoxymethyl) 1h 1,2,3 triazol 1 yl]phenyl]sulfonyl] 1,2,3,4 tetrahydroisoquinoline
6,7 dimethoxy 2 [[3 [4 [(4 ethylphenoxy)methyl] 1h 1,2,3 triazol 1 yl]phenyl]sulfonyl] 1,2,3,4 tetrahydroisoquinoline
6,7 dimethoxy 2 [[3 [4 [(4 propylphenoxy)methyl] 1h 1,2,3 triazol 1 yl]phenyl]sulfonyl] 1,2,3,4 tetrahydroisoquinoline
6,7 dimethoxy 2 [[3 [4 [(4 tolyloxy)methyl] 1h 1,2,3 triazol 1 yl]phenyl]sulfonyl] 1,2,3,4 tetrahydroisoquinoline
6,7 dimethoxy 2 [[3 [4 [(naphthalen 2 yloxy)methyl] 1h 1,2,3 triazol 1 yl]phenyl]sulfonyl] 1,2,3,4 tetrahydroisoquinoline
6,7 dimethoxy 2 [[3 [4 [4 (trifluoromethyl)phenyl] 1h 1,2,3 triazol 1 yl]phenyl]sulfonyl] 1,2,3,4 tetrahydroisoquinoline
6,7 dimethoxy 2 [[3 [4 [[4 (tert butyl)phenoxy]methyl] 1h 1,2,3 triazol 1 yl]phenyl]sulfonyl] 1,2,3,4 tetrahydroisoquinoline
aromatase inhibitor
tetrahydroisoquinoline
triazole
unclassified drug
[1 [3 [(6,7 dimethoxy 3,4 dihydroisoquinolin 2(1h) yl)sulfonyl]phenyl] 1h 1,2,3 triazol 4 yl]methyl adamantane 1 carboxylate
[1 [3 [(6,7 dimethoxy 3,4 dihydroisoquinolin 2(1h) yl)sulfonyl]phenyl] 1h 1,2,3 triazol 4 yl]methyl benzoate
aromatase inhibitor
tetrahydroisoquinoline derivative
triazole derivative
alkylation
Article
cytotoxicity
drug synthesis
enzyme active site
human
hydrogen bond
IC50
molecular docking
priority journal
structure activity relation
chemistry
drug screening
procedures
spectroscopy
synthesis
tumor cell line
Aromatase Inhibitors
Cell Line, Tumor
Drug Screening Assays, Antitumor
Humans
Hydrogen Bonding
Inhibitory Concentration 50
Molecular Docking Simulation
Spectrum Analysis
Structure-Activity Relationship
Tetrahydroisoquinolines
Triazoles
Issue Date: 2019
Abstract: Novel thirteen triazole-tetrahydroisoquinoline derivatives (2a-m) were synthesized and evaluated for their aromatase inhibitory activities. Seven triazoles showed significant aromatase inhibitory activity (IC50 = 0.07–1.9 μM). Interestingly, the analog bearing naphthalenyloxymethyl substituent at position 4 of the triazole ring (2i) displayed the most potent aromatase inhibitory activity (IC50 = 70 nM) without significant cytotoxicity to a normal cell. Molecular docking also suggested that the direct H-bonding interaction with residue Thr310 may be responsible for a striking inhibitory effect of the most potent compound 2i. © 2019 Elsevier Inc.
URI: https://www.scopus.com/inward/record.uri?eid=2-s2.0-85073107177&doi=10.1016%2fj.bioorg.2019.103327&partnerID=40&md5=d993e1f6df5ce14efacb18134bcece56
http://ir.swu.ac.th/jspui/handle/123456789/12238
ISSN: 452068
Appears in Collections:SCOPUS 1983-2021

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