Synthesis of Secondary Amines of Bornylamine and Isobornylamine Containing a Saturated N-Heterocycle and Study of Their Antiviral Activity against Respiratory Syncytial Virus

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Synthesis of Secondary Amines of Bornylamine and Isobornylamine Containing a Saturated N-Heterocycle and Study of Their Antiviral Activity against Respiratory Syncytial Virus. / Tishchenko, S. A.; Sokolova, A. S.; Yarovaya, O. I. et al.

In: Russian Journal of General Chemistry, Vol. 95, No. 1, 27.02.2025, p. 79-87.

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

BibTeX

@article{1c1bf5c9163c480e93f15d216c6703d0,

title = "Synthesis of Secondary Amines of Bornylamine and Isobornylamine Containing a Saturated N-Heterocycle and Study of Their Antiviral Activity against Respiratory Syncytial Virus",

abstract = "Abstract: Natural compounds are actively used as promising starting molecules for the development of new antiviral drugs. In this paper, a method was proposed for the synthesis of new derivatives of bicyclic monoterpenoids using endo- and exo-bornylamines as starting materials. It was shown that alkylation of (+)-exo-bornylamine and (+)- or (–)-endo-bornylamine with 2-chloro-1-morpholinoethanone, 2-chloro-1-(piperidin-1-yl)ethanone and 2-chloro-1-(4-methylpiperidin-1-yl)ethanone in the presence of potassium carbonate as a base leads to the corresponding secondary amines. In order to study the effect of the amide group on the antiviral activity, some of the prepared compounds were reduced to amines. It was found that the exo-bornylamine derivative containing the 4-methylpiperidine fragment has pronounced antiviral activity against the respiratory syncytial virus.",

keywords = "bornylamine, camphor, respiratory syncytial virus",

author = "Tishchenko, {S. A.} and Sokolova, {A. S.} and Yarovaya, {O. I.} and Krasnov, {V. I.} and Shtro, {A. A.} and Galochkina, {A. V.} and Klabukov, {A. M.} and Razgulyaeva, {D. N.} and Salakhutdinov, {N. F.}",

note = "This work was financially supported by the Russian Science Foundation (grant no. 24-13-00134). Synthesis of Secondary Amines of Bornylamine and Isobornylamine Containing a Saturated N-Heterocycle and Study of Their Antiviral Activity against Respiratory Syncytial Virus / S. A. Tishchenko, A. S. Sokolova, O. I. Yarovaya [et al.] // Russian Journal of General Chemistry. – 2025. – Vol. 95, No. 1. – P. 79-87. – DOI 10.1134/S1070363224613486",

year = "2025",

month = feb,

day = "27",

doi = "10.1134/S1070363224613486",

language = "English",

volume = "95",

pages = "79--87",

journal = "Russian Journal of General Chemistry",

issn = "1070-3632",

publisher = "Maik Nauka-Interperiodica Publishing",

number = "1",

}

RIS

TY - JOUR

T1 - Synthesis of Secondary Amines of Bornylamine and Isobornylamine Containing a Saturated N-Heterocycle and Study of Their Antiviral Activity against Respiratory Syncytial Virus

AU - Tishchenko, S. A.

AU - Sokolova, A. S.

AU - Yarovaya, O. I.

AU - Krasnov, V. I.

AU - Shtro, A. A.

AU - Galochkina, A. V.

AU - Klabukov, A. M.

AU - Razgulyaeva, D. N.

AU - Salakhutdinov, N. F.

N1 - This work was financially supported by the Russian Science Foundation (grant no. 24-13-00134). Synthesis of Secondary Amines of Bornylamine and Isobornylamine Containing a Saturated N-Heterocycle and Study of Their Antiviral Activity against Respiratory Syncytial Virus / S. A. Tishchenko, A. S. Sokolova, O. I. Yarovaya [et al.] // Russian Journal of General Chemistry. – 2025. – Vol. 95, No. 1. – P. 79-87. – DOI 10.1134/S1070363224613486

PY - 2025/2/27

Y1 - 2025/2/27

N2 - Abstract: Natural compounds are actively used as promising starting molecules for the development of new antiviral drugs. In this paper, a method was proposed for the synthesis of new derivatives of bicyclic monoterpenoids using endo- and exo-bornylamines as starting materials. It was shown that alkylation of (+)-exo-bornylamine and (+)- or (–)-endo-bornylamine with 2-chloro-1-morpholinoethanone, 2-chloro-1-(piperidin-1-yl)ethanone and 2-chloro-1-(4-methylpiperidin-1-yl)ethanone in the presence of potassium carbonate as a base leads to the corresponding secondary amines. In order to study the effect of the amide group on the antiviral activity, some of the prepared compounds were reduced to amines. It was found that the exo-bornylamine derivative containing the 4-methylpiperidine fragment has pronounced antiviral activity against the respiratory syncytial virus.

AB - Abstract: Natural compounds are actively used as promising starting molecules for the development of new antiviral drugs. In this paper, a method was proposed for the synthesis of new derivatives of bicyclic monoterpenoids using endo- and exo-bornylamines as starting materials. It was shown that alkylation of (+)-exo-bornylamine and (+)- or (–)-endo-bornylamine with 2-chloro-1-morpholinoethanone, 2-chloro-1-(piperidin-1-yl)ethanone and 2-chloro-1-(4-methylpiperidin-1-yl)ethanone in the presence of potassium carbonate as a base leads to the corresponding secondary amines. In order to study the effect of the amide group on the antiviral activity, some of the prepared compounds were reduced to amines. It was found that the exo-bornylamine derivative containing the 4-methylpiperidine fragment has pronounced antiviral activity against the respiratory syncytial virus.

KW - bornylamine

KW - camphor

KW - respiratory syncytial virus

UR - https://www.mendeley.com/catalogue/2f14a3c7-31c7-31d0-9a65-e7befd78ddda/

UR - https://www.scopus.com/record/display.uri?eid=2-s2.0-85219642869&origin=inward&txGid=e8b69b44f516d3bed8f0cc1fe1a05f71

UR - https://www.elibrary.ru/item.asp?id=80408870

U2 - 10.1134/S1070363224613486

DO - 10.1134/S1070363224613486

M3 - Article

VL - 95

SP - 79

EP - 87

JO - Russian Journal of General Chemistry

JF - Russian Journal of General Chemistry

SN - 1070-3632

IS - 1

ER -

ID: 64959910