Palladium-Catalyzed Carbonylation of (Hetero)Aryl, Alkenyl and Allyl Halides by Means of <i>N-</i>Hydroxysuccinimidyl Formate as CO Surrogate

Barré, Anaïs; Ţînţaş, Mihaela-Liliana; Alix, Florent; Gembus, Vincent; Papamicaël, Cyril; Levacher, Vincent

doi:10.1021/acs.joc.5b01119

Cited by 29 publications

(26 citation statements)

References 49 publications

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“…Next, compound 8 was reacted with the activated succinimidyl ester 10 prepared according to our previously described synthesis [45], to afford product 12 at a 71% yield (Scheme 3). Under the same reaction conditions, with the succinimidyl ester 11 as reactant, compound 13 was also prepared, in order to demonstrate the influence of the carbamate at the C-5 position on the AChE inhibitory activity.…”

Section: Resultsmentioning

confidence: 99%

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Design, Synthesis, and In Vitro Biological Activities of a Bio-Oxidizable Prodrug to Deliver Both ChEs and DYRK1A Inhibitors for AD Therapy

et al. 2019

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Despite their side effects, cholinesterase (ChE) inhibitors remain the only approved drugs to treat Alzheimer’s disease patients, along with the N-methyl-d-aspartate (NMDA) receptor antagonist memantine. In the last few years, the dual-specificity tyrosine phosphorylation-regulated kinase 1A (DYRK1A) has also been studied as a promising target for the development of new drugs for this pathology. In this context, and based on our previous characterization of bio-oxidizable prodrugs of potent acetylcholinesterase (AChE) inhibitors, we envisioned a strategy involving the synthesis of a bio-oxidizable prodrug of both ChE and DYRK1A inhibitors. To this end, we fixed our interest on a known potent inhibitor of DYRK1A, namely INDY. The designed prodrug of both ChE and DYRK1A inhibitors was successfully synthesized, connecting both inhibitors by a carbonate link. This prodrug and its corresponding drug were then evaluated as ChEs and DYRK1A inhibitors. Remarkably, in vitro results were in accordance with the starting hypothesis, showing a relative inactivity of the prodrug against DYRK1A and ChEs and a potent inhibition of ChEs by the oxidized form. Molecular docking and kinetic studies of ChE inhibition by the active compound are also discussed in this report.

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Section: Resultsmentioning

confidence: 99%

“…High-resolution mass spectrometry (HRMS) was carried out on a Waters LCT XE spectrometer (WATERS, Guyancourt, France). Compounds 10 and 3 were synthesized using a previously described synthesis [44,45].…”

Section: Methodsmentioning

confidence: 99%

Design, Synthesis, and In Vitro Biological Activities of a Bio-Oxidizable Prodrug to Deliver Both ChEs and DYRK1A Inhibitors for AD Therapy

et al. 2019

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“…Levahcer et al described in 2015 the Pd-catalyzed carbonylation of (hetero)aryl, alkenyl, and alkyl halides with N -hydroxysuccinimidyl formate as CO surrogate [78]. A large range of aryl, vinyl, allyl, and benzyl halides can be transformed into the corresponding NHS esters in good to excellent yields under mild conditions (60 °C/10 h/2-MeTHF; Scheme 16).…”

Section: Use Of 2-methf In Transition Metal Catalyzed Chemistrymentioning

confidence: 99%

Recent advancements on the use of 2-methyltetrahydrofuran in organometallic chemistry

et al. 2016

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Since the introduction of 2-methyltetrahydrofuran as an useful alternative to the classical tetrahydrofuran, there has been a continuous interest in the synthetic community operating at academic and industrial towards it. In particular, the much higher stability that basic organometallic reagents display in 2-methyltetrahydrofuran makes it suitable for processes involving such sensitive species including asymmetric transformations. The easy formation of an azeotropic mixture with water, the substantial immiscibility with water, and the fact it derives from natural sources (corncobs or bagasse), allow to consider it in agreement with the Anastas’ Geen Chemistry principles. In this minireview, selected examples of its employment in organometallic transformations ranging from carbanions to radical and transition metal-catalyzed processes are provided.Graphical abstract

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“…Others used halobenzyl alcohols under radical conditions [34,35] or halobenzoic acid and N,N′-succinimidyl carbonate [36]. Transition metal catalyzed reactions are also applied such as palladium catalyzed coupling reactions with CO [37] or with formyl derivatives [38] as well as Ru-catalyzed reactions using the respective benzaldehyde [39].…”

Section: X-ray Structure Determinationmentioning

confidence: 99%

X-ray Structures of Succinimidyl Halobenzoates

2017

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Abstract:The crystal and molecular structures of five succinimidyl halobenzoates are reported. Corresponding derivatives with the respective halo-radionuclide ( 18 F, 76 Br, 123 I/ 124 I/ 125 I/ 131 I) were prepared and used for the radiolabeling of biologically active (macro-)molecules (peptides, proteins, antibodies) under mild labeling conditions. All compounds were crystalized from petroleum ether/ethyl acetate mixtures.

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Palladium-Catalyzed Carbonylation of (Hetero)Aryl, Alkenyl and Allyl Halides by Means of N-Hydroxysuccinimidyl Formate as CO Surrogate

Cited by 29 publications

References 49 publications

Design, Synthesis, and In Vitro Biological Activities of a Bio-Oxidizable Prodrug to Deliver Both ChEs and DYRK1A Inhibitors for AD Therapy

Design, Synthesis, and In Vitro Biological Activities of a Bio-Oxidizable Prodrug to Deliver Both ChEs and DYRK1A Inhibitors for AD Therapy

Recent advancements on the use of 2-methyltetrahydrofuran in organometallic chemistry

X-ray Structures of Succinimidyl Halobenzoates

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