Synthesis and antiviral activity of sulfur-containing derivatives of adamantane

Klimochkin, Yu. N.; Моисеев, И. К.; Abramov, O. V.; Vladyko, G. V.; Korobchenko, L. V.; Бореко, Е. И.

doi:10.1007/bf00772006

Cited by 19 publications

(8 citation statements)

References 2 publications

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“…The resulting mixture was stirred at 2 h at r.t, followed by TLC, then the aqueous phase was separated and extracted several times with DCM, dried over anhydrous Na 2 SO 4 and concentrated. The crude product was purified through flash chromatography (AcOEt/n-hexane 9:1 as the eluent) to get Memit as a clear oil 31 . 1H NMR (CDCl 3 –400 MHz): δ 0.84 (s, 6H), 1.12 (s, 2H), 1.24–1.34 (s, 4H), 1.47–1.69 (m, 4H), 1.77–1.78 (m, 2H), 2.11–2.16 (m, 1H) ppm.…”

Section: Methodsmentioning

confidence: 99%

Memantine prodrug as a new agent for Alzheimer’s Disease

Sestito

Daniele

Pietrobono

et al. 2019

Sci Rep

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Hydrogen sulphide has recently drawn much attention due to its potent anti-inflammatory and neuroprotective roles in brain functions. The purpose of the current study was to exploit these beneficial properties of H2S to design a new agent for the treatment of Alzheimer’s disease (AD). To pursue our aims, we replaced the free amine group of memantine with an isothiocyanate functionality as a putative H2S-donor moiety. The new chemical entity, named memit, was then tested in vitro to determine whether it retains the pharmacological profile of the “native drug”, while also providing a source of H2S in the CNS. Indeed, Memit showed the ability to release H2S through a cysteine-mediated mechanism, thus generating memantine. Moreover, the new hybrid molecule exerts protective effects against neuronal inflammation and induces a drastic fall in ROS production. In addition, memit was also able to reduce the Aβ(1-42) self-induced aggregation and exerted cytoprotective effect against Aβ oligomers-induced damage in both human neurons and rat microglia cells. Finally, similarly to memantine, the new compound promotes autophagy, a complex process required for cellular homeostasis in cell survival that results to be altered in neurodegenerative diseases. In conclusion, our study revealed that memit is a prodrug of memantine. Further in vivo studies will be necessary to fully investigate the synergic or cumulative effects due to the H2S-releasing moiety and the native drug.

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Section: Methodsmentioning

confidence: 99%

Memantine prodrug as a new agent for Alzheimer’s Disease

Sestito

Daniele

Pietrobono

et al. 2019

Sci Rep

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“…Selenocarbamates, a group of organoselenium compounds, act as precursors for α‐alkylidene‐β/δ‐lactams exhibiting antibiotic properties 9. The antiviral effects of compounds containing this framework have also been studied 10 . N ‐Substituted Se ‐phenylselenocarbamates are useful precursors for the generation of carbamoyl radicals and other synthetic transformations 11.…”

Section: Introductionmentioning

confidence: 99%

Oxidative C–Se Coupling of Formamides and Diselenides by Using Aqueous tert‐Butyl Hydroperoxide: A Convenient Synthesis of Selenocarbamates

et al. 2013

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“…The main reason is that such compounds, especially amino derivatives, exhibit strong biological activity due to lipophilic nature of the compact cage-like core and its considerable volume [136][137][138][139]. Many amines of the adamantane series possess antiviral activity; some adamantane amine hydrochlorides are well known antiviral drugs (amantadine, rimantadine) [140][141][142][143].…”

Section: Amino Alcohols Of the Adamantane Seriesmentioning

confidence: 99%

Cage-like amino alcohols. synthesis, reactions, and application

Kas’yan

Пальчиков

2010

Russ J Org Chem

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The review analyzes methods for the synthesis of amino alcohols containing cage-like norbornene, norbornane, and adamantane fragments. Such reactions of amino alcohols as selective functionalization of hydroxy and amino groups, as well as heterocyclizations with formation of nitrogen-and oxygen-containing heterocycles, are considered. Biological activity of cage-like amino alcohols and their derivatives and their use as ligands in catalytic asymmetric syntheses are discussed.

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Synthesis and antiviral activity of sulfur-containing derivatives of adamantane

Cited by 19 publications

References 2 publications

Memantine prodrug as a new agent for Alzheimer’s Disease

Memantine prodrug as a new agent for Alzheimer’s Disease

Oxidative C–Se Coupling of Formamides and Diselenides by Using Aqueous tert‐Butyl Hydroperoxide: A Convenient Synthesis of Selenocarbamates

Cage-like amino alcohols. synthesis, reactions, and application

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Synthesis and antiviral activity of sulfur-containing derivatives of adamantane

Cited by 19 publications

References 2 publications

Memantine prodrug as a new agent for Alzheimer’s Disease

Memantine prodrug as a new agent for Alzheimer’s Disease

Oxidative C–Se Coupling of Formamides and Diselenides by Using Aqueous tert‐But­yl Hydroperoxide: A Convenient Synthesis of Selenocarbamates

Cage-like amino alcohols. synthesis, reactions, and application

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Product

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Oxidative C–Se Coupling of Formamides and Diselenides by Using Aqueous tert‐Butyl Hydroperoxide: A Convenient Synthesis of Selenocarbamates