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

Burmistrov, V. V.; Kuznetsov, Y. P.; Novikov, V. V.; Abbas Saeef, M. H.; Davidenko, A. V.; Vernigora, A. A.; Butov, G. M.

doi:10.7868/S3034630425030017

PII

S30346304S0514749225030017-1

DOI

10.7868/S3034630425030017

Publication type

Article

Status

Published

Authors

V. V. Burmistrov

Affiliation:
Volgograd State Technical University (VSTU)
Volzhsky polytechnic institute (branch) VSTU

Y. P. Kuznetsov

Affiliation:
Volgograd State Technical University (VSTU)
Volzhsky polytechnic institute (branch) VSTU

V. V. Novikov

Affiliation:
Volgograd State Technical University (VSTU)
Volzhsky polytechnic institute (branch) VSTU

M. H. Abbas Saeef

Affiliation: Volgograd State Technical University (VSTU)

A. V. Davidenko

Affiliation: Volgograd State Technical University (VSTU)

A. A. Vernigora

Affiliation: Volgograd State Technical University (VSTU)

G. M. Butov

Affiliation:
Volgograd State Technical University (VSTU)
Volzhsky polytechnic institute (branch) VSTU

Volume/ Edition

Volume 61 / Issue number 3

Pages

221-229

Abstract

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.

Keywords

природные соединения бицикло[2.2.1]гептан изоцианат изотиоцианат мочевина галогенсодержащие ароматические изоцианаты растворимая эпоксидгидролаза оптическая изомерия

Date of publication

24.12.2022

Year of publication

2022

Number of purchasers

Views

References

1. 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
2. Romashov L.V., Ananikov V.P. Org. Biomol. Chem. 2016, 14, 10593-10598. doi 10.1039/C6OB01731B
3. Galkin K., Ananikov V.P. Chem. Sus. Chem. 2019, 12, 2976-2982. doi 10.1002/cssc.201900592
4. 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
5. Aslani Z., Hassani A., Mandoulakani B.A., Barin M., Maleki R. Scientia Horticulturae. 2023, 309, 111610. doi 10.1016/j.scienta.2022.111610
6. Ameredes B.T., Calhoun W.J., Barnes P.J. Am. J. Respir. Crit. Care Med. 2006, 174, 965-969. doi 10.1164/rccm.2606001
7. 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
8. 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
9. 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
10. 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
11. 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

GOST	Abbas Saeef M., Burmistrov V., Butov G., Davidenko A., Kuznetsov Y., Novikov V., Vernigora A. 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 // Russian Journal of Organic Chemistry. – 2025. – V. 61. – Issue number 3 C. 221-229 . URL: https://orgchemras.ru/s30346304s0514749225030017-1/?version_id=119397. DOI: 10.7868/S3034630425030017
MLA	Abbas Saeef, M. H, Burmistrov, V. V, Butov, G. M, Davidenko, A. V, Kuznetsov, Y. P, Novikov, V. V, Vernigora, A. A "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." Russian Journal of Organic Chemistry. 61.3 (2025).:221-229. DOI: 10.7868/S3034630425030017
APA	Abbas Saeef M., Burmistrov V., Butov G., Davidenko A., Kuznetsov Y., Novikov V., Vernigora A. (2025). 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. Russian Journal of Organic Chemistry. vol. 61, no. 3, pp.221-229 DOI: 10.7868/S3034630425030017

RAS Chemistry & Material ScienceЖурнал органической химии Russian Journal of Organic Chemistry

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

You can

References

Индексирование

RAS Chemistry & Material ScienceЖурнал органической химии Russian Journal of Organic Chemistry

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

You can

References

Индексирование

Via social network