Stereoselective synthesis of novel adamantane derivatives with high potency against rimantadine-resistant influenza A virus strains

Kuznetsov, N. Yu.; Tikhov, Rabdan M.; Godovikov, Ivan A.; Medvedev, Michael G.; Burtseva, Elena; Кириллова, Е. С.; Bubnov, Yurii N.

doi:10.1039/c7ob00331e

Cited by 18 publications

(7 citation statements)

References 43 publications

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“…( R ) - isomers of compounds 4 and 5 were synthesized from the corresponding ( R ) -N -Boc-derivative of adamantyl homoallylamine 1 , according to the procedures described in [ 18 ]. For each experiment, freshly made solutions of compounds 4 , 5 and RMT in 50% DMSO were used.…”

Section: Methodsmentioning

confidence: 99%

Efficacy of (R)-6-Adamantane-Derivatives of 1,3-Oxazinan-2-One and Piperidine-2,4-Dione in The Treatment of Mice Infected by the A/California/04/2009 influenza Virus

et al. 2021

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The World Health Organization (WHO) recommends antivirals as an additional line of defense against influenza. One of such drugs is rimantadine. However, most of the circulating strains of influenza A viruses are resistant to this drug. Thus, a search for analogs effective against rimantadine-resistant viruses is of the utmost importance. Here, we examined the efficiency of two adamantane azaheterocyclic rimantadine derivatives on a mouse model of pneumonia caused by the rimantadine-resistant influenza A virus /California/04/2009 (H1N1). BALB/c mice inoculated with the virus were treated with two doses (15 mg and 20 mg/kg a day) of tested analogs via oral administration for 5 days starting 4 hours before the infection. The efficacy was assessed by survival rate, mean day to death, weight loss, and viral titer in the lungs. Oral treatment with both compounds in both doses protected 60100% of the animals, significantly increased the survival rate, and abolished weight loss. The treatments also inhibited virus titer in the lungs in comparison to the control group. This treatment was more effective compared to rimantadine at the same scheme and dosage. Moreover, the study of the sensitivity of the virus isolated from the lungs of the treated mice and grown in MDCK cells showed that no resistance had emerged during the 5 days of treatment with both compounds.

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Section: Methodsmentioning

confidence: 99%

Efficacy of (R)-6-Adamantane-Derivatives of 1,3-Oxazinan-2-One and Piperidine-2,4-Dione in The Treatment of Mice Infected by the A/California/04/2009 influenza Virus

et al. 2021

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“…The most powerful compounds were both enantiomers of the enol ester 13 (Fig. 19) exhibiting IC value equals to 7.7 µM with the 2016 Orenburg strain [33]. Guoxin et al performed modifications on the structure of an original compound appointed from high throughput screening.…”

Section: Piperidine Derivatives With Antiviral Activitymentioning

confidence: 99%

Piperidine nucleus in the field of drug discovery

Abdelshaheed¹,

Fawzy

El‐Subbagh

et al. 2021

Futur J Pharm Sci

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Background Piperidine is an essential heterocyclic system and a pivotal cornerstone in the production of drugs. Piperidine byproducts showed several important pharmacophoric features and are being utilized in different therapeutic applications. Main text Piperidine derivatives are being utilized in different ways as anticancer, antiviral, antimalarial, antimicrobial, antifungal, antihypertension, analgesic, anti-inflammatory, anti-Alzheimer, antipsychotic and/or anticoagulant agents. Conclusions This review article sheds a light on the most recent studies proving the importance of piperidine nucleus in the field of drug discovery.

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“…The same reaction applied to the imine derived from adamantyl aldehyde 176 gave the expected homoallyl amine 177 , which was further desulfinylated to give the expected amine, isolated as its Boc derivative (Scheme 77). [100] …”

Section: Organozinc Compoundsmentioning

confidence: 99%

Chiral N‐tert‐Butylsulfinyl Imines: New Discoveries

Foubelo

Yus

2020

The Chemical Record

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In this account the reactions of chiral N‐tert‐butylsulfinyl imines with organometallic reagents such as organoalkaline (lithium, sodium, potassium and cesium derivatives), organomagnesium, organozinc, organoboron, organoaluminium, organoindium and organosilicon compounds is comprehensively described. The reactivity in all cases is derived to synthetic applications in order to prepare interesting organic nitrogenated molecules, especially in the field of alkaloid compounds.

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Stereoselective synthesis of novel adamantane derivatives with high potency against rimantadine-resistant influenza A virus strains

Cited by 18 publications

References 43 publications

Efficacy of (R)-6-Adamantane-Derivatives of 1,3-Oxazinan-2-One and Piperidine-2,4-Dione in The Treatment of Mice Infected by the A/California/04/2009 influenza Virus

Efficacy of (R)-6-Adamantane-Derivatives of 1,3-Oxazinan-2-One and Piperidine-2,4-Dione in The Treatment of Mice Infected by the A/California/04/2009 influenza Virus

Piperidine nucleus in the field of drug discovery

Chiral N‐tert‐Butylsulfinyl Imines: New Discoveries

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