Synthesis of N-heterocyclic amides based on (+)-camphoric acid and study of their antiviral activity and pharmacokinetics

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Synthesis of N-heterocyclic amides based on (+)-camphoric acid and study of their antiviral activity and pharmacokinetics. / Yarovaya, O I; Baranova, D V; Sokolova, A S et al.

In: Russian Chemical Bulletin, Vol. 72, No. 3, 03.2023, p. 807-818.

Research output: Contribution to journal › Article › peer-review

BibTeX

@article{d0760b1f4d8449f8918a36d723b6f4c7,

title = "Synthesis of N-heterocyclic amides based on (+)-camphoric acid and study of their antiviral activity and pharmacokinetics",

abstract = "Efficient conditions for the synthesis of nitrogen-containing heterocyclic derivatives of (1R,3S)(+)-camphoric acid were selected. A series of heterocyclic compounds based on (+)-camphoric acid bearing pharmacophoric fragments was synthesized using the developed methodology. The compounds were tested for their antiviral activity against SARS-CoV-2 and H1N1 influenza viruses, and efficient inhibitors were identified that are of significant interest for further studies. The stability of the compounds and pharmaco-kinetics of the leader compound were studied when administered intragastrically and intramuscularly to mice at a dose of 200 mg kg-1 using the HPLC-MS/MS method.",

keywords = "(+)-camphoric acid, A H1N1 influenza virus, N-heterocycles, SARS-CoV-2 virus, pharmacokinetics",

author = "Yarovaya, {O I} and Baranova, {D V} and Sokolova, {A S} and Nemolochnova, {A G} and Sal'nikova, {O P} and Fat'anova, {A V} and Rogachev, {A D} and Volobueva, {A S} and Zarubaev, {V V} and Pokrovsky, {A G} and Salakhutdinov, {N F}",

note = "This work fi nancially supported by the Ministry of Science and Higher Education of the Russian Federation (Projects Nos FWUE-2022-0007, 122040400033-9; N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry (Siberian Branch of the Russian Academy of Sciences)). Biological assays toward infl uenza virus were carried out in terms of state assignment of the Pasteur Institute of Epidemiology and Microbiology (St. Petersburg, Russia) (Project No. AAAA-A21-121030200272-6). {\textcopyright} Springer Science+Business Media LLC 2023.",

year = "2023",

month = mar,

doi = "10.1007/s11172-023-3845-9",

language = "English",

volume = "72",

pages = "807--818",

journal = "Russian Chemical Bulletin",

issn = "1066-5285",

publisher = "Springer Nature",

number = "3",

}

RIS

TY - JOUR

T1 - Synthesis of N-heterocyclic amides based on (+)-camphoric acid and study of their antiviral activity and pharmacokinetics

AU - Yarovaya, O I

AU - Baranova, D V

AU - Sokolova, A S

AU - Nemolochnova, A G

AU - Sal'nikova, O P

AU - Fat'anova, A V

AU - Rogachev, A D

AU - Volobueva, A S

AU - Zarubaev, V V

AU - Pokrovsky, A G

AU - Salakhutdinov, N F

N1 - This work fi nancially supported by the Ministry of Science and Higher Education of the Russian Federation (Projects Nos FWUE-2022-0007, 122040400033-9; N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry (Siberian Branch of the Russian Academy of Sciences)). Biological assays toward infl uenza virus were carried out in terms of state assignment of the Pasteur Institute of Epidemiology and Microbiology (St. Petersburg, Russia) (Project No. AAAA-A21-121030200272-6). © Springer Science+Business Media LLC 2023.

PY - 2023/3

Y1 - 2023/3

N2 - Efficient conditions for the synthesis of nitrogen-containing heterocyclic derivatives of (1R,3S)(+)-camphoric acid were selected. A series of heterocyclic compounds based on (+)-camphoric acid bearing pharmacophoric fragments was synthesized using the developed methodology. The compounds were tested for their antiviral activity against SARS-CoV-2 and H1N1 influenza viruses, and efficient inhibitors were identified that are of significant interest for further studies. The stability of the compounds and pharmaco-kinetics of the leader compound were studied when administered intragastrically and intramuscularly to mice at a dose of 200 mg kg-1 using the HPLC-MS/MS method.

AB - Efficient conditions for the synthesis of nitrogen-containing heterocyclic derivatives of (1R,3S)(+)-camphoric acid were selected. A series of heterocyclic compounds based on (+)-camphoric acid bearing pharmacophoric fragments was synthesized using the developed methodology. The compounds were tested for their antiviral activity against SARS-CoV-2 and H1N1 influenza viruses, and efficient inhibitors were identified that are of significant interest for further studies. The stability of the compounds and pharmaco-kinetics of the leader compound were studied when administered intragastrically and intramuscularly to mice at a dose of 200 mg kg-1 using the HPLC-MS/MS method.

KW - (+)-camphoric acid

KW - A H1N1 influenza virus

KW - N-heterocycles

KW - SARS-CoV-2 virus

KW - pharmacokinetics

UR - https://www.scopus.com/record/display.uri?eid=2-s2.0-85153255240&origin=inward&txGid=429f12c445eb1bdf69c936229f4d4e4e

UR - https://www.mendeley.com/catalogue/63f67054-12c2-31d5-a4ed-d800b46c0a54/

U2 - 10.1007/s11172-023-3845-9

DO - 10.1007/s11172-023-3845-9

M3 - Article

C2 - 37089866

VL - 72

SP - 807

EP - 818

JO - Russian Chemical Bulletin

JF - Russian Chemical Bulletin

SN - 1066-5285

IS - 3

ER -

ID: 48739858