Synthesis and Anti-Proliferative Activity of New Biphenyle-Benzylidenethiazolidine- 2,4-dione Bis-Adducts Containing Various Heterocyclic Cores

Meyer, Maxime; Kuntz, Sandra; Grillier-Vuissoz, Isabelle; Martin, Hélène; Richert, Lysiane; Flament, Stéphane; Chapleur, Yves; Boisbrun, Michel

doi:10.2174/15701808113106660080

Cited by 4 publications

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“…Thus, it could be interesting to determine if our dual molecules also display anti-proliferative activity. We already reported [37] the anti-proliferative activities of unsaturated synthetic intermediates 30, 31, 40, 41, 51, 52 and of unsaturated analogues of compounds 32, 33, 44, and 45. Mainly, the anti-proliferative activity was observed with compounds bearing t-butyl protecting groups.…”

Section: Tablementioning

confidence: 96%

“…In order to follow strategy B, we used imidazole and triazole heterocycles as central templates and grafted on them chemical moieties intended to hold AT 1 and PPAR-γ activities. We already reported [37] the three-steps synthesis of unsaturated derivatives 30 and 31 from freshly prepared tert-butyl-4' (bromomethyl)biphenyl-2-carboxylate and commercially available imidazole derivatives (Scheme 4). Reduction of the double bond and removal of tert-butyl ester afforded 32 and…”

Section: Chemistrymentioning

confidence: 99%

“…We also used 1,2,3-triazole as a heterocyclic template in order to follow strategy B (Scheme 6). We already reported [37] the synthesis of unsaturated derivatives 40 and 41 by a "click chemistry" cycloaddition reaction from tert-butyl-4' (azidomethyl)biphenyl-2-carboxylate and appropriate alkynes, followed by condensation with TZD. Catalytic hydrogenation easily gave saturated compounds 42 and 43.…”

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confidence: 99%

“…In order to follow strategy C, we intended to graft a 4′-methylbiphenyl-2-carboxylate moiety on a molecule of troglitazone. We already reported [37] a three-step synthesis of unsaturated compounds 51 and 52. Catalytic hydrogenation of 51 afforded reduced compound 53 which after acid deprotection gave target compound 54 (Scheme 8).…”

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confidence: 99%

“…2). Thus, we coupled the already reported [37] molecule 55 with tyrosine derivative 23 (Scheme 9), affording 56. Cleavage of both t-butyl esters with TFA at room temperature was quite troublesome, since we observed a partial concomitant cleavage of the…”

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confidence: 99%

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Synthesis and evaluation of new designed multiple ligands directed towards both peroxisome proliferator-activated receptor-γ and angiotensin II type 1 receptor

Meyer

Foulquier

Dupuis

et al. 2018

European Journal of Medicinal Chemistry

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Because of the complex biological networks, many pathologic disorders fail to be treated with a molecule directed towards a single target. Thus, combination therapies are often necessary, but they have many drawbacks. An alternative consists in building molecules intended to interact with multiple targets, called designed multiple ligands. We followed such a strategy in order to treat metabolic syndrome, by setting up molecules directed towards both type 1 angiotensin II (AT) receptor and peroxisome proliferator-activated receptor-γ (PPAR-γ). For this purpose, many molecules were prepared by merging both pharmacophores following three different strategies. Their ability to activate PPAR-γ and to block AT receptors were evaluated in vitro. This strategy led to the preparation of many new PPAR-γ activating and AT blocking molecules. Among them, some exhibited both activities, highlighting the convenience of this approach.

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Section: Tablementioning

confidence: 96%

Section: Chemistrymentioning

confidence: 99%

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confidence: 99%

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confidence: 99%

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confidence: 99%

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Synthesis and evaluation of new designed multiple ligands directed towards both peroxisome proliferator-activated receptor-γ and angiotensin II type 1 receptor

Meyer

Foulquier

Dupuis

et al. 2018

European Journal of Medicinal Chemistry

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Casting light on synthetic, SC-XRD and quantum mechanical studies for 2,1-benzothiazine based bis-adducts

Ahmad

Khalid

et al. 2023

Journal of Molecular Structure

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Photoisomerization of Arylidene Heterocycles: Toward the Formation of Fused Heterocyclic Quinolines

et al. 2022

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We report herein the photoinduced isomerization of a series of arylidene heterocycles 1. The photoreaction mechanism was investigated by a combined UV–vis/photo-NMR spectroscopic study, and we showed that Ar-TZDs exhibit a positive P-type photochromism, which limits their isomerization efficiency. By exploring the solvatochromism in a series of solvents, the conditions favoring the conversion toward one or the other stereoisomer have been studied, in particular by choosing the appropriate wavelengths. Finally, the extension of this photoisomerization study was proposed with a convenient preparation of various fused heterocyclic quinolines in good overall yields.

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Synthesis and Anti-Proliferative Activity of New Biphenyle-Benzylidenethiazolidine- 2,4-dione Bis-Adducts Containing Various Heterocyclic Cores

Cited by 4 publications

References 0 publications

Synthesis and evaluation of new designed multiple ligands directed towards both peroxisome proliferator-activated receptor-γ and angiotensin II type 1 receptor

Synthesis and evaluation of new designed multiple ligands directed towards both peroxisome proliferator-activated receptor-γ and angiotensin II type 1 receptor

Casting light on synthetic, SC-XRD and quantum mechanical studies for 2,1-benzothiazine based bis-adducts

Photoisomerization of Arylidene Heterocycles: Toward the Formation of Fused Heterocyclic Quinolines

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