Synthesis and properties of 1,3-disubstituted ureas and its isosteric analogs containing polycyclic fragments: XIX.  Exo -isomers of 1-(1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl)-3- R  ureas and thioureas

V. V. Burmistrov; Бурмистров Владимир Владимирович; Y. P. Kuznetsov; Кузнецов Ярослав Петрович; V. V. Novikov; Новиков Владимир Васильевич; M. H. Abbas Saeef; Аббас Саиф Мухаммед Хасан; A. V. Davidenko; Давиденко Андрей Владимирович; A. A. Vernigora; Вернигора Андрей Александрович; G. M. Butov; Бутов Геннадий Михайлович

doi:10.31857/S0514749225030017

Synthesis and properties of 1,3-disubstituted ureas and its isosteric analogs containing polycyclic fragments: XIX. Exo-isomers of 1-(1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl)-3-R ureas and thioureas

Авторлар: Burmistrov V.V.¹^,2, Kuznetsov Y.P.¹^,2, Novikov V.V.¹^,2, Abbas Saeef M.H.¹, Davidenko A.V.¹, Vernigora A.A.¹, Butov G.M.¹^,2
Мекемелер:
1. Volgograd State Technical University (VSTU)
2. Volzhsky polytechnic institute (branch) VSTU
Шығарылым: Том 61, № 3 (2025)
Беттер: 221-229
Бөлім: ЭКСПЕРИМЕНТАЛЬНЫЕ СТАТЬИ
URL: https://ter-arkhiv.ru/0514-7492/article/view/687753
DOI: https://doi.org/10.31857/S0514749225030017
EDN: https://elibrary.ru/ESYCGF
ID: 687753

Дәйексөз келтіру

Толық мәтін

Ашық рұқсат
Рұқсат жабық

Рұқсат берілді
Рұқсат жабық

Рұқсат ақылы немесе тек жазылушылар үшін

Аннотация
Толық мәтін
Авторлар туралы
Әдебиет тізімі
Қосымша файлдар
Статистика

Аннотация

For a comprehensive assessment of the enantiomeric stereospecificity of human soluble epoxide hydrolase (hsEH), 1,3-disubstituted ureas and thioureas containing a bornyl fragment in their structure were synthesized according to the reaction exo-(R or S)-1,1,7-trimethylbicyclo[2.2.1]heptane-2-amine with aromatic isocyanates and isothiocyanates with yields up to 99%. Synthesized compounds are promising inhibitors of hsEH.

Негізгі сөздер

natural compounds, bicyclo[2.2.1]heptane, isocyanate, isothiocyanate, urea, halogenated aromatic isocyanates, soluble epoxide hydrolase, optical isomerism, racemate

Толық мәтін

Авторлар туралы

V. Burmistrov

Volgograd State Technical University (VSTU); Volzhsky polytechnic institute (branch) VSTU

Email: butov@post.volpi.ru
ORCID iD: 0000-0002-8547-9166
Ресей, Leninskii prosp., 28, Volgograd, 400005; ul. Engelsa, 42a, Volzhsky, 404121

Y. Kuznetsov

Volgograd State Technical University (VSTU); Volzhsky polytechnic institute (branch) VSTU

Email: butov@post.volpi.ru
ORCID iD: 0000-0002-1933-2684
Ресей, Leninskii prosp., 28, Volgograd, 400005; ul. Engelsa, 42a, Volzhsky, 404121

V. Novikov

Volgograd State Technical University (VSTU); Volzhsky polytechnic institute (branch) VSTU

Email: butov@post.volpi.ru
ORCID iD: 0000-0001-5022-7172
Ресей, Leninskii prosp., 28, Volgograd, 400005; ul. Engelsa, 42a, Volzhsky, 404121

M. Abbas Saeef

Volgograd State Technical University (VSTU)

Email: butov@post.volpi.ru
ORCID iD: 0000-0002-2050-9926
Ресей, Leninskii prosp., 28, Volgograd, 400005

A. Davidenko

Volgograd State Technical University (VSTU)

Email: butov@post.volpi.ru
ORCID iD: 0000-0002-4205-0810
Ресей, Leninskii prosp., 28, Volgograd, 400005

A. Vernigora

Volgograd State Technical University (VSTU)

Email: butov@post.volpi.ru
ORCID iD: 0000-0001-6456-0910
Ресей, Leninskii prosp., 28, Volgograd, 400005

G. Butov

Volgograd State Technical University (VSTU); Volzhsky polytechnic institute (branch) VSTU

Хат алмасуға жауапты Автор.
Email: butov@post.volpi.ru
ORCID iD: 0000-0002-0839-4513
Ресей, Leninskii prosp., 28, Volgograd, 400005; ul. Engelsa, 42a, Volzhsky, 404121

Әдебиет тізімі

Burmistrov V.V., Zapravdina D.M., Savelyev E.N., Orlinson B.S., Butov G.M., Novakov I.A. Russ. J. Org. Chem. 2024, 60, 12. doi: 10.1134/S1070428024010020
Romashov L.V., Ananikov V.P. Org. Biomol. Chem. 2016, 14, 10593–10598. doi: 10.1039/C6OB01731B
Galkin K., Ananikov V.P. Chem. Sus. Chem. 2019, 12, 2976–2982. doi: 10.1002/cssc.201900592
Raffo A., Baiamonte I., De Benedetti L., Lupotto E., Marchioni I., Nardo N., Cervelli C. Food Chem. 2023, 404, 134532. doi: 10.1016/j.foodchem.2022.134532
Aslani Z., Hassani A., Mandoulakani B.A., Barin M., Maleki R. Scientia Horticulturae. 2023, 309, 111610. doi: 10.1016/j.scienta.2022.111610
Ameredes B.T., Calhoun W.J., Barnes P.J. Am. J. Respir. Crit. Care Med. 2006, 174, 965–969. doi: 10.1164/rccm.2606001
Manickam M., Pillaiyar T., Boggu P.R., Venkateswararao E., Jalani H.B., Kim N.-D., Lee S.K., Jeon J.S., Kim S.K., Jung S.-H. Eur. J. Med. Chem. 2016, 117, 113–124. doi: 10.1016/j.ejmech.2016.04.015
Burmistrov V., Morisseau C., Karlov D., Pitushkin D., Vernigora A., Rasskazova E., Butov G.M., Hammock B.D. Bioorg. Med. Chem. Lett. 2020, 30, 127430. doi: 10.1016/j.bmcl.2020.127430
Брунилин Р.В., Вернигора А.А., Вострикова О.В., Давиденко А.В., Навроцкий М.Б., Салыкин Н.А., Новаков И.А. Изв. акад. Наук Сер. хим. 2022, 71, 1662–1669 [Brunilin R.V., Vernigora A.A., Vostrikova O.V., Davidenko A.V., Nawrozkij M.B., Salykin N.A. Novakov I. A. Russ. Chem. Bull. (Engl. Transl.) 2022, 71, 1662–1669]. doi: 10.1007/s11172-022-3576-1
Burmistrov V., Morisseau C., Pitushkin D., Fayzullin R.R., Karlov D., Vernigora A., Kuznetsov Y., Abbas S.M.H., Butov G.M., Hammock B.D. Results Chem. 2022, 4, 100653. doi: 10.1016/j.rechem.2022.100653