Synthesis and Properties of 1,3-Disubstituted Ureas and Its Isosteric Analogs Containing Polycyclic Fragments: XVIII. 1-[2-(Adamantan-2-yl)ethyl]-3-R-Ureas and Thioureas

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Resumo

Methods for the preparation of 1-[2-(adamantan-2-yl)ethyl]-3-R-ureas and thioureas by the reaction of 2-(adamantan-2-yl)ethylamine with aromatic isocyanates and isothiocyanates with 36–87% yields were developed. It was found that the displacement of the ethylene bridge from the 1st to the 2nd position of the adamantyl radical does not significantly affect the value of log P and melting points of the corresponding compounds.

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Sobre autores

V. Burmistrov

Volgograd State Technical University (VSTU)

Autor responsável pela correspondência
Email: vburmistrov@vstu.ru
ORCID ID: 0000-0002-8547-9166
Rússia, Volgograd

D. Zapravdina

Volgograd State Technical University (VSTU)

Email: vburmistrov@vstu.ru
ORCID ID: 0000-0002-8654-2382
Rússia, Volzhsky

E. Savelyev

Volgograd State Technical University (VSTU)

Email: vburmistrov@vstu.ru
ORCID ID: 0000-0002-1937-768X
Rússia, Volgograd

B. Orlinson

Volgograd State Technical University (VSTU)

Email: vburmistrov@vstu.ru
ORCID ID: 0000-0002-4710-4718
Rússia, Volgograd

G. Butov

Volgograd State Technical University (VSTU); Volzhsky Polytechnic Institute (branch) VSTU

Email: butov@post.volpi.ru
ORCID ID: 0000-0002-0839-4513
Rússia, Volgograd; Volzhsky

I. Novakov

Volgograd State Technical University (VSTU)

Email: vburmistrov@vstu.ru
ORCID ID: 0000-0002-0980-6591
Rússia, Volgograd

Bibliografia

  1. Гладких Б.П, Дьяченко В.С., Данилов Д.В., Матюхина А.К., Бурмистров В.В., Бутов Г.М. ЖОрХ. 2022, 58, 1135–1144. [Gladkikh B.P., D’yachenko V.S., Danilov D.V., Matyukhina A.K., Burmistrov V.V., Butov G.M. Russ. J. Org. Chem. 2022, 58, 1561–1568.]. doi: 10.31857/S0514749222110015
  2. Schmelzer K.R., Kubala L., Newman J.W., Kim I.H., Eiserich J.P., Hammock B.D. Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 9772–9777. doi: 10.1073/pnas.0503279102
  3. Fleming I., Rueben A., Popp R., Fisslthaler B., Schrodt S., Sander A., Haendeler J., Falck J.R., Morisseau C., Hammock B.D., Busse R. Arterioscler. Thromb Vasc. Biol. 2007, 27, 2612–2618. doi: 10.1161/ATVBAHA.107.152074
  4. Imig J.D. Expert Opin. Drug Metab. Toxicol. 2008, 4, 165–174. doi: 10.1517/17425255.4.2.165
  5. Burmistrov V., Morisseau C., Pitushkin D., Karlov D., Fayzullin R.R., Butov G.M., Hammock B.D. Bioorg. Med. Chem. Lett. 2019, 28, 2302–2313. doi: 10.1016/j.bmcl.2018.05.024
  6. Burmistrov V., Morisseau C., D’yachenko V., Rybakov V.B., Butov G.M., Hammock B.D. J. Fluor. Chem. 2019, 220, 48–53. doi: 10.1016/j.jfluchem.2019.02.005
  7. Бурмистров В.В., Бутов Г.М., Карлов Д.С., Палюлин В.А., Зефиров Н.С., Мориссье К., Хэммок Б.Д. Биоорг. хим. 2016, 42, 448–459. [Burmistrov V.V., Butov G.M., Karlov D.S., Palyulin V.A., Zefirov N.S., Morisseau C., Hammock B.D. Russ. J. Bioorg. Chem. 2016, 42, 404–414.]. doi: 10.1134/S1068162016030067
  8. Новаков И.А., Орлинсон Б.С., Мамутова Н.Н., Савельев Е.Н., Потаенкова Е.А., Пынтя Л.А., Наход М.А. ЖОрХ. 2016, 86, 924–928. [Novakov I.A., Orlinson B.S., Mamutova N.N., Savel’ev E.N., Potayonkova E.A., Pyntya L.A., Nakhod M.A. Russ. J. Org. Chem. 2016, 86, 1255–1258.]. doi: 10.1134/S1070363216060062
  9. Murashkina A.V., Kuliukhina D.S., Averin A.D., Abel A.S., Savelyev E.N., Orlinson B.S., Novakov I.A., Correiac C.R.D., Beletskaya I.P. Mendeleev Commun. 2022, 32, 91–93. doi: 10.1016/j.mencom.2022.01.029
  10. Kharlamova A.D., Abel A.S., Averin A.D., Maloshitskaya O.A., Roznyatovskiy V.A., Savelyev E.N., Orlinson B.S., Novakov I.A., Beletskaya I.P. Molecules. 2021, 26, 1910. doi: 10.3390/molecules26071910
  11. Sedenkova K.N., Dueva E.V., Averina E.B., Grishin Y.K., Osolodkin D.I., Kozlovskaya L.I., Palyulin V.A., Savelyev E.N., Orlinson B.S., Novakov I.A., Butov G.M., Kuznetsova T.S., Karganova G.G., Zefirov N.S. Org. Biomol. Chem. 2015, 13, 3406–3415. doi: 10.1039/C4OB02649G
  12. Meden A., Knez D., Jukič M., Brazzolotto X., Gršič M., Pišlar A., Zahirović A., Kos J., Nachon F., Svete J., Gobec S., Grošelj U. Chem. Commun. 2019, 55, 3765–3768. doi: 10.1039/C9CC01330J
  13. Bohmer V., Meshcheryakov D., Thondorf I., Bolte M. Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 2004, 60, O136−O139. doi: 10.1107/S0108270103027586
  14. Meshcheryakov D., Arnaud-Neu F., Bohmer V., Bolte M., Hubscher-Bruder V., Jobin E., Thondorf I., Werner S. Org. Biomol. Chem. 2008, 6, 1004−1014. doi: 10.1039/B718114K
  15. Burmistrov V., Morisseau C., Pitushkin D., Karlov D., Fayzullin R.R., Butov G.M., Hammock B.D. Bioorg. Med. Chem. Lett. 2018, 28, 2302–2313. doi: 10.1016/j.bmcl.2018.05.024
  16. Burmistrov V., Morisseau C., Harris T.R., Butov G., Hammock B.D. Bioorg. Chem. 2018, 76, 510–527. doi: 10.1016/j.bioorg.2017.12.024

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2. Compounds containing 2-(adamantan-2-yl)ethyl fragments exhibiting biological activity

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