, 6R)-2-(acetoxymethyl)-6-(prop-2-yn-1-yloxy)tetrahydro-2H
, 00 g, 16.65 mmol) in acetic anhydride (20.46 mL, 216.47 mmol) was added sodium acetate (1.50 g, 18.32 mmol) under argon. The mixture was refluxed during 2 h and cooled to room temperature before being cooled in an ice bath. Water (50 mL) was added and the suspension was filtered
, CDCl 3 ): ? 1.42 (m, 9H, chromane CH 3 + linker CH 2 ), 1.91 (m, 3H, chromane 3-HaHb + triazole-CH 2 -CH 2 ), 1.98 (s, 3H, COCH 3 ), 2.00 (s, 3H, COCH 3 ), 2.03 (s, 3H, COCH 3 ), 2.09 (s, 6H, COCH 3 + chromane CH 3 ), 2.12 (m, 1H, chromane 3-HaHb), 2.14 (s, 3H, chromane CH 3 ), 2.19 (s, 3H, chromane CH 3 ), 2.59 (m, 2H, linker CH 2 ), 2.66 (m, 2H, chromane 4-H), 3.59 (d, J = 2.3 Hz, 2H, CH 2 CO), 3.74 (X part of an ABX system, ylidene)methyl)phenoxy)methyl)-2,5,7,8-tetramethylchroman-6-yl)hexyl)-1H-1,2,3-triazol-4-yl)methoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate (30) To a mixture of 28 (138 mg, 0.26 mmol) and 29 (100 mg, 0.26 mmol) were added t-BuOH (20 mL) and MeOH (2 mL) and sonication was applied. To the resulting solution was added a mixture of CuSO 4 (58 mg, 0.36 mmol) and sodium ascorbate (71 mg, 0.36 mmol) in water (0.5 mL), vol.1, pp.88-90
, 09 mL, 1.15 mg/mL) was added at room temperature and stirred under argon for 1 h. Amberlite ® IR 120H was added until neutral pH and the suspension was filtered to give after evaporation of the filtrate an orange liquid which was purified by reverse-phase column chromatography (eluent: H 2 O (0.1% TFA)/MeOH, 90:10 to 10:90) to afford after lyophilisation 71 mg (0.09 mmol, 100 % yield) of white powder, hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)methyl)-1H-1,2,3-triazol-1-yl)hexyl)chroman-2-yl)methoxy)benzylidene)pyrrolidine-2,5-dione (31) A suspension of compound 30 (87 mg, 0.09 mmol) in anhydrous MeOH (5 mL) was sonicated until dissolution. A solution of MeONa in MeOH, vol.525, pp.126-128, 1043.
These cell lines were grown at 37 °C under 5% CO 2 in Dulbecco's Modified Eagle Medium (DMEM, Gibco ® , Thermo Fisher Scientific, Villebon-sur-Yvette, France) for MCF-7, Hs578T, U87, and HCT116, and Roswell Park Memorial Institute (RPMI) 1640 medium (Gibco ® ) for MDA-MB-231 and MDA-MB-453. These phenol red containing media were supplemented with 2 mM L-glutamine, MDA-MB-453 and Hs578T human breast cancer cell lines, HCT116 colon cancer cell line, and U87 glioblastoma cell line were obtained from American Type Culture Collection, vol.50 ,
Global cancer statistics 2018: GLOBOCAN estimates of incidence and mortality worldwide for 36 cancers in 185 countries, CA: A Cancer Journal for Clinicians, vol.68, pp.394-424, 2018. ,
Treatment of Breast Cancer, AFP, vol.81, pp.1339-1346, 2010. ,
Biological determinants of endocrine resistance in breast cancer, Nature Reviews Cancer, vol.9, pp.631-643, 2009. ,
Trastuzumab: Updated Mechanisms of Action and Resistance in Breast Cancer, Front. Oncol, vol.2, 2012. ,
Molecular Pathways: Regulation and Therapeutic Implications of Multidrug Resistance, Clin Cancer Res, vol.18, pp.1863-1869, 2012. ,
Targeting the Molecular Subtypes of Triple Negative Breast Cancer: Understanding the Diversity to Progress the Field, The Oncologist, vol.22, pp.1086-1093, 2017. ,
Therapeutic journey of 2,4-thiazolidinediones as a versatile scaffold: An insight into structure activity relationship, European Journal of Medicinal Chemistry, vol.129, pp.218-250, 2017. ,
Biological potential of thiazolidinedione derivatives of synthetic origin, Chemistry Central Journal, vol.11, p.130, 2017. ,
Thiazolidine-2,4-dione derivatives: Programmed chemical weapons for key protein targets of various pathological conditions, Bioorganic & Medicinal Chemistry, vol.23, pp.2953-2974, 2015. ,
Erosion of the chronic myeloid leukaemia stem cell pool by PPAR? agonists, Nature, vol.525, pp.380-383, 2015. ,
New insights into antidiabetic drugs: Possible applications in cancer treatment, Chemical Biology & Drug Design, vol.90, pp.1056-1066, 2017. ,
Synthesis of new troglitazone derivatives: Anti-proliferative activity in breast cancer cell lines and preliminary toxicological study, European Journal of Medicinal Chemistry, vol.51, pp.206-215, 2012. ,
URL : https://hal.archives-ouvertes.fr/hal-00746870
Optimization of troglitazone derivatives as potent anti-proliferative agents: Towards more active and less toxic compounds, European Journal of Medicinal Chemistry, vol.83, pp.129-140, 2014. ,
URL : https://hal.archives-ouvertes.fr/hal-01094539
Reprofiling of troglitazone towards more active and less toxic derivatives: a new hope for cancer treatment?, Current Topics in Medicinal Chemistry, vol.16, pp.2115-2124, 2016. ,
URL : https://hal.archives-ouvertes.fr/hal-01281602
Investigation of the role of the thiazolidinedione ring of troglitazone in inducing hepatotoxicity, Toxicology Letters, vol.192, pp.141-149, 2010. ,
Pyrrolidinediones reduce the toxicity of thiazolidinediones and modify their anti-diabetic and anti-cancer properties, European Journal of Pharmacology, vol.697, pp.13-23, 2012. ,
A Short and Convenient Chemical Route to Optically Pure 2-Methyl Chromanmethanols. Total Asymmetric Synthesis of ?-, ?-, and ?-Tocotrienols, J. Org. Chem, vol.72, pp.6735-6741, 2007. ,
Zur Kenntnis der Dioxydiphenylsulfone, Journal Für Praktische Chemie, vol.160, pp.41-64, 1942. ,
A kinetic resolution route to the (S)-chromanmethanol intermediate for synthesis of the natural tocols, Tetrahedron: Asymmetry, vol.8, pp.20-27, 1997. ,
Enantioselective transesterification of (±)-6-benzyloxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-ylmethanol catalyzed by the Amano PS lipase in the ionic liquid [bmim]PF6, Russ Chem Bull, vol.59, pp.2129-2132, 2010. ,
Ferrocene derivatives of liquid chiral molecules allow assignment of absolute configuration by X-ray crystallography, Tetrahedron: Asymmetry, vol.28, pp.1321-1329, 2017. ,
From D-glucuronic acid to L-iduronic acid derivatives via a radical tandem decarboxylation-cyclization, Carbohydrate Research, vol.386, pp.99-105, 2014. ,
URL : https://hal.archives-ouvertes.fr/hal-01494402
, Reactions of Carbohydrates, pp.211-215, 1963.
Synthesis of saccharinglycoconjugates targeting carbonic anhydrase using a one-pot cyclization/deprotection strategy, Carbohydrate Research, vol.476, pp.65-70, 2019. ,
The Evolving Role of Tumor Treating Fields in Managing Glioblastoma: Guide for Oncologists, Am J Clin Oncol, vol.41, pp.191-196, 2018. ,
Metabolic Pathways of the Warburg Effect in Health and Disease: Perspectives of Choice, Chain or Chance, International Journal of Molecular Sciences, vol.18, p.2755, 2017. ,
Cancer Energy Metabolism: Shutting Power off Cancer Factory, Biomolecules & Therapeutics, vol.26, pp.39-44, 2018. ,
Glucose conjugation for the specific targeting and treatment of cancer, Chemical Science, vol.4, p.2319, 2013. ,
?2-Troglitazone promotes cytostatic rather than pro-apoptotic effects in breast cancer cells cultured in high serum conditions, Cell Cycle, vol.15, pp.3402-3412, 2016. ,
NMR Chemical Shifts of Common Laboratory Solvents as Trace Impurities, J. Org. Chem, vol.62, pp.7512-7515, 1997. ,