Sequential synthesis of a new analogue of amlodipine bearing a short amino polyethyleneglycol chain

Legeay, Jean Christophe; Eynde, Jean Jacques Vanden; Bazureau, Jean Pierre

doi:10.1016/j.tet.2007.08.111

Cited by 14 publications

(15 citation statements)

References 26 publications

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“…2-[2-(2-azidoethoxy)ethoxy]ethanol was synthesised by a modification of the method of Legeay et al . [28] 2-[2-(2-aminoethoxy)ethoxy]ethanol was synthesised by the procedure of Liu et al . [29] 2-[2-(2-azidoethoxy)ethoxy]ethyl mesylate was synthesised by a modification of the procedure of Sakamoto et al .…”

Section: Methodsmentioning

confidence: 99%

A Warburg effect targeting vector designed to increase the uptake of compounds by cancer cells demonstrates glucose and hypoxia dependent uptake

2019

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Glycoconjugation to target the Warburg effect provides the potential to enhance selective uptake of anticancer or imaging agents by cancer cells. A Warburg effect targeting group, rationally designed to facilitate uptake by glucose transporters and promote cellular accumulation due to phosphorylation by hexokinase (HK), has been synthesised. This targeting group, the C2 modified glucose analogue 2-(2-[2-(2-aminoethoxy)ethoxy]ethoxy)-D-glucose, has been conjugated to the fluorophore nitrobenzoxadiazole to evaluate its effect on uptake and accumulation in cancer cells. The targeting vector has demonstrated inhibition of glucose phosphorylation by HK, indicating its interaction with the enzyme and thereby confirming the potential to facilitate an intracellular trapping mechanism for compounds it is conjugated with. The cellular uptake of the fluorescent analogue is dependent on the glucose concentration and is so to a greater extent than is that of the widely used fluorescent glucose analogue, 2-NBDG. It also demonstrates selective uptake in the hypoxic regions of 3D spheroid tumour models whereas 2-NBDG is distributed primarily through the normoxic regions of the spheroid. The increased selectivity is consistent with the blocking of alternative uptake pathways.

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Section: Methodsmentioning

confidence: 99%

A Warburg effect targeting vector designed to increase the uptake of compounds by cancer cells demonstrates glucose and hypoxia dependent uptake

2019

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“…Upon completion, the reaction mixture was cooled to room temperature and extracted with Et 2 O (3×25 mL), and the organic extracts were combined. After removal of the solvent, the crude product was purified by column chromatography on silica gel with EtOAc/n-hexane (1:3 7, 66.6, 126.9, 128.2, 128.4, 128.6, 129.2, 132.7, 135.4, 139.9, 171.7 3, 43.9, 65.5, 126.2, 127.7, 128.1, 128.9, 129.5, 131.8, 134.4, 137.8, 171.4 38.8, 65.8, 122.6, 122.9, 126.6, 126.9, 128.1, 128.6, 129.0, 132.7, 134.6, 139.9, 171.7 m,H PhC ),m,3,4,7.94 (2H,m,2,6-H PhS ); 13 C NMR (CDCl 3 ): δ 33. 8, 43.2, 65.4, 122.4, 123.0, 126.7, 126.9, 127.9, 128.5, 129.4, 132.4, 134.1, 139.3, 171.5; MS: m/z (%) 400 (7.9, M-C 9 H 9 O), 392 (27.1, M-C 6 H 5 SO 2 ); Anal.…”

Section: Methodsmentioning

confidence: 99%

Organic reactions in ionic liquids: MgO as efficient and reusable catalyst for the Michael addition of sulfonamides to α,β-unsaturated esters under microwave irradiation

Hasaninejad¹,

Khalafi-Nezhad²,

Zare³

et al. 2007

Arkivoc

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“…The heterocyclic ring in DHP is a common feature of various bioactive compounds such as anticonvulsant, antidiabetic, antianxiety, antidepressive, antitumor, analgesic, sedative, vasodilator, bronchodilator, hypnotic and anti-inflammatory agents 2 . DHPs are commercially used as calcium channel blockers for the treatment of cardiovascular diseases including hypertension 3 .…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Experimental and DFT Studies on the Crystal Structure, Ftir, ¹h NMR and 13c NMR Spectra of Drivatives of Dihydropyridines

Fekri

Nikpassan

2012

J. Chil. Chem. Soc.

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Several derivatives of dihydropyridines are prepared through the condensation of aldehydes, dimedone and NH 4 OAc in H 2 O, in the presence of a catalytic amount of nano-Fe 3 O 4 . The crystalline products were characterized by FTIR, 1 H NMR and 13 C NMR. Density Functional Theory (DFT) calculations at the B3LYP level is used to optimize the geometries of isolated molecules, and to calculate the, FTIR, 1 H NMR and 13 C NMR spectra of selected synthesized compounds. We found that the DFT B3LYP calculated FTIR, 1 H NMR and 13 C NMR spectra are in accordance with the experimental data.

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Sequential synthesis of a new analogue of amlodipine bearing a short amino polyethyleneglycol chain

Cited by 14 publications

References 26 publications

A Warburg effect targeting vector designed to increase the uptake of compounds by cancer cells demonstrates glucose and hypoxia dependent uptake

A Warburg effect targeting vector designed to increase the uptake of compounds by cancer cells demonstrates glucose and hypoxia dependent uptake

Organic reactions in ionic liquids: MgO as efficient and reusable catalyst for the Michael addition of sulfonamides to α,β-unsaturated esters under microwave irradiation

Synthesis, Experimental and DFT Studies on the Crystal Structure, Ftir, ¹h NMR and 13c NMR Spectra of Drivatives of Dihydropyridines

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