Synthesis and biological evaluation of C-13′ substituted 7′- homo -anhydrovinblastine derivatives

Gherbovet, Olga; Spisa, Fabio La; Thoret, Sylviane; Alvarez, María Concepción García; Lévaique, Hélène; Bignon, Jérôme; Roussi, Fanny

doi:10.1016/j.bmcl.2015.02.045

Cited by 5 publications

(1 citation statement)

References 13 publications

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“…To assess if modified vinca compounds could be good Pgp inhibitors, we decided to evaluate a wide range of substrates functionalized on ring A′ and/or C′, playing with the size, the location, and the orientation of the substituents. In fact, we recently disclosed the elaboration of new analogues of VLN 3 or of various C-12′-functionalized VLN derivatives by an innovative ring enlargement. , These compounds scan a large chemical space around velbenamine. Among all the derivatives elaborated by this strategy, we intentionally chose 7 – 15 (Figure ).…”

Section: Introductionmentioning

confidence: 99%

Original Vinca Derivatives: From P-Glycoprotein Substrates to P-Glycoprotein Inhibitors

et al. 2016

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The first example of vinca derivatives 16-18 able to modulate P-glycoprotein (Pgp) efflux activity is reported. They were elaborated in two steps from vinorelbine 3 (VLN) by a modification of the velbenamine moiety. These compounds were able to decrease efficiently Pgp mediated influx and efflux of rhodamine-123 (Rho) and to restore the cytotoxicity of vinorelbine 3 (VLN) and doxorubicin (Dox) on K562R (dox-resistant) cell lines.

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Section: Introductionmentioning

confidence: 99%

Original Vinca Derivatives: From P-Glycoprotein Substrates to P-Glycoprotein Inhibitors

et al. 2016

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Synthesis and antiproliferativeactivity of new vinca alkaloids containing an α,β-unsaturated aromatic side chain

Ngo

Nguyen

et al. 2015

Bioorganic & Medicinal Chemistry Letters

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Pd(II)-Catalyzed C4-Selective Alkynylation of Indoles by a Transient Directing Group

Zhang,

Yuan

et al. 2024

Org. Lett.

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With alanine as a transient directing group, Pdcatalyzed regioselective alkynylation at the indole C4-position was successfully established in a good yield. The total synthesis of the PAF antagonist demonstrated the synthetic utility of this protocol. The regioselectivity was explicitly proven by the prepared C4selective palladacycle intermediate in the catalytic process and the DFT calculation of the energy barriers of C4-and C2-site-selective C−H activation of indole.

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Synthesis and biological evaluation of C-13′ substituted 7′- homo -anhydrovinblastine derivatives

Cited by 5 publications

References 13 publications

Original Vinca Derivatives: From P-Glycoprotein Substrates to P-Glycoprotein Inhibitors

Original Vinca Derivatives: From P-Glycoprotein Substrates to P-Glycoprotein Inhibitors

Synthesis and antiproliferativeactivity of new vinca alkaloids containing an α,β-unsaturated aromatic side chain

Pd(II)-Catalyzed C4-Selective Alkynylation of Indoles by a Transient Directing Group

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