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

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

Journal

Russian Chemical Bulletin
ISSN: 1066-5285 , E-ISSN: 1573-9171

Output data

Year: 2023, Volume: 72, Number: 3, Pages: 807-818 Pages count : 12 DOI: 10.1007/s11172-023-3845-9

Tags

(+)-camphoric acid, N-heterocycles, A H1N1 infl uenza virus, SARS-CoV-2 virus, pharmacokinetics

Authors

Yarovaya O.I. ^1,2 , Baranova D.V. ¹ , Sokolova A.S. ¹ , Nemolochnova A.G. ^1,2 , Sal’nikova O.P. ² , Fat’anova A.V. ² , Rogachev A.D. ^1,2 , Volobueva A.S. ³ , Zarubaev V.V. ³ , Pokrovsky A.G. ² , Salakhutdinov N.F. ¹

Affiliations

1	N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 prosp. Akademika Lavrent´eva, 630090 Novosibirsk, Russian Federation.
2	Novosibirsk State University, 2 ul. Pirogova, 630090 Novosibirsk, Russian Federation
3	Pasteur Institute of Epidemiology and Microbiology, 14 ul. Mira, 197101 St. Petersburg, Russian Federation

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.

Yarovaya O.I. , Baranova D.V. , Sokolova A.S. , Nemolochnova A.G. , Sal’nikova O.P. , Fat’anova A.V. , Rogachev A.D. , Volobueva A.S. , Zarubaev V.V. , Pokrovsky A.G. , Salakhutdinov N.F.
Synthesis of N-heterocyclic amides based on (+)-camphoric acid and study of their antiviral activity and pharmacokinetics
Russian Chemical Bulletin. 2023. V.72. N3. P.807-818. DOI: 10.1007/s11172-023-3845-9 WOS Scopus РИНЦ OpenAlex

Яровая О.И. , Баранова Д.В. , Соколова А.С. , Немолочнова А.Г. , Сальникова О.П. , Фатьянова А.В. , Рогачев А.Д. , Волобуева А.С. , Зарубаев В.В. , Покровский А.Г. , Салахутдинов Н.Ф.
Синтез N-гетероциклических амидов на основе (+)-камфорной кислоты, изучение их противовирусной активности и фармакокинетики
Известия Академии наук. Серия химическая.(RUSS CHEM B+). 2023. Т.72. №3. С.807-818. РИНЦ

Submitted:	Dec 8, 2022
Accepted:	Jan 29, 2023
Published online:	Apr 15, 2023

Web of science:	WOS:001031662300023
Scopus:	2-s2.0-85153255240
Elibrary:	61235421
OpenAlex:	W4365812337

DB	Citing
OpenAlex	6
Web of science	5
Scopus	4