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

封面

如何引用文章

全文:

开放存取 开放存取
受限制的访问 ##reader.subscriptionAccessGranted##
受限制的访问 订阅存取

详细

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.

全文:

受限制的访问

作者简介

V. Burmistrov

Volgograd State Technical University (VSTU)

编辑信件的主要联系方式.
Email: vburmistrov@vstu.ru
ORCID iD: 0000-0002-8547-9166
俄罗斯联邦, Volgograd

D. Zapravdina

Volgograd State Technical University (VSTU)

Email: vburmistrov@vstu.ru
ORCID iD: 0000-0002-8654-2382
俄罗斯联邦, Volzhsky

E. Savelyev

Volgograd State Technical University (VSTU)

Email: vburmistrov@vstu.ru
ORCID iD: 0000-0002-1937-768X
俄罗斯联邦, Volgograd

B. Orlinson

Volgograd State Technical University (VSTU)

Email: vburmistrov@vstu.ru
ORCID iD: 0000-0002-4710-4718
俄罗斯联邦, Volgograd

G. Butov

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

Email: butov@post.volpi.ru
ORCID iD: 0000-0002-0839-4513
俄罗斯联邦, Volgograd; Volzhsky

I. Novakov

Volgograd State Technical University (VSTU)

Email: vburmistrov@vstu.ru
ORCID iD: 0000-0002-0980-6591
俄罗斯联邦, Volgograd

参考

  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

补充文件

附件文件
动作
1. JATS XML
2. Compounds containing 2-(adamantan-2-yl)ethyl fragments exhibiting biological activity

下载 (101KB)
3. Scheme 1

下载 (141KB)
4. Scheme 2

下载 (54KB)
5. Scheme 3

下载 (62KB)

版权所有 © Russian Academy of Sciences, 2024