ArticleChemMedChem2014
Tetrahydroisoquinolinone-based steroidomimetic and chimeric microtubule disruptors.
Article in ChemMedChem, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 11 papers.
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Who cites it
11 citing papers in PubMed.
- Isolation, Total Synthesis and Anti-Diabetic Activity of Filiforidine fromMolecules (Basel, Switzerland) · 2025Article
- Total Synthesis of the Racemate of Laurolitsine.Molecules (Basel, Switzerland) · 2024Article
- Cell Fate following Irradiation of MDA-MB-231 and MCF-7 Breast Cancer Cells Pre-Exposed to the Tetrahydroisoquinoline Sulfamate Microtubule Disruptor STX3451.Molecules (Basel, Switzerland) · 2022Article
- Screening of σJournal of medicinal chemistry · 2022Article
- The Pictet-Spengler Reaction Updates Its Habits.Molecules (Basel, Switzerland) · 2020Review
- Nonsteroidal sulfamate derivatives as new therapeutic approaches for Neurofibromatosis 2 (NF2).BMC pharmacology & toxicology · 2019Article
- Article
- Modes of cell death induced by tetrahydroisoquinoline-based analogs in MDA-MB-231 breast and A549 lung cancer cell lines.Drug design, development and therapy · 2018Article
- Discovery and Development of the Aryl O-Sulfamate Pharmacophore for Oncology and Women's Health.Journal of medicinal chemistry · 2015Article
- Article
- Synthesis, anti-tubulin and antiproliferative SAR of steroidomimetic dihydroisoquinolinones.ChemMedChem · 2014Article
Corrections and comments
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Authors and funding
9 authors.
Funding
Abstract
A structure-activity relationship (SAR) translation strategy was used for the discovery of tetrahydroisoquinoline (THIQ)-based steroidomimetic and chimeric microtubule disruptors based upon a steroidal starting point. A steroid A,B-ring-mimicking THIQ core was connected to methoxyaryl D-ring ring mimics through methylene, carbonyl and sulfonyl linkers to afford a number of steroidomimetic hits (e.g., 7-methoxy-2-(3- methoxybenzyl)-6-sulfamoyloxy-1,2,3,4-tetrahydroisoquinoline (20 c) GI₅₀=2.1 μM). Optimisation and control experiments demonstrate the complementary SAR of this series and the steroid derivatives that inspired its design. Linkage of the THIQ-based A,B-mimic with the trimethoxyaryl motif prevalent in colchicine site binding microtubule disruptors delivered a series of chimeric molecules whose activity (GI₅₀=40 nM) surpasses that of the parent steroid derivatives. Validation of this strategy was obtained from the excellent oral activity of 7-methoxy-6-sulfamoyloxy-2-(3,4,5-trimethoxybenzyl)-1,2,3,4-tetrahydroisoquinoline relative to a benchmark steroidal bis- sulfamate in an in vivo model of multiple myeloma.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.