Synthesis and Properties of 1,3-Disubstituted Ureas and Their Isosteric Analogues Containing Polycyclic Fragments. XVII. 1-[(3-Bromadamantan-1-yl)]-3-R-Ureas and Symmetric Diureas

Cover Page

Cite item

Full Text

Open Access Open Access
Restricted Access Access granted
Restricted Access Subscription Access

Abstract

A series of 1,3-disubstituted ureas and diureas was synthesized by the reaction of (3-bromoadamantan-1-yl)isocyanate with aliphatic diamines, fluorine-containing anilines, and trans-4-amino-(cyclohexyloxy)benzoic acid in 36–85% yields. Hydrolysis of (3-bromoadamantan-1-yl)isocyanate in the presence of catalytic amounts of DBU afforded symmetrical 1,3-bis-((3-bromadamantan-1-yl)urea in 60% yield. are promising inhibitors of human soluble epoxide hydrolase hsEH.

Full Text

Restricted Access

About the authors

B. P. Gladkikh

Volgograd state technical university (VSTU)

Author for correspondence.
Email: butov@post.volpi.ru
ORCID iD: 0000-0001-6271-0479
Russian Federation, Volgograd

V. S. D’yachenko

Volgograd state technical university (VSTU)

Email: butov@post.volpi.ru
Russian Federation, Volgograd

D. V. Danilov

Volgograd state technical university (VSTU)

Email: butov@post.volpi.ru
ORCID iD: 0000-0001-8734-2617
Russian Federation, Volgograd

A. K. Matyukhina

Institute of General and Inorganic Chemistry. N.S. Kurnakov RAS

Email: butov@post.volpi.ru
ORCID iD: 0000-0002-2831-6838
Russian Federation, Moscow

V. V. Burmistrov

Volgograd state technical university (VSTU)

Email: butov@post.volpi.ru
ORCID iD: 0000-0002-8547-9166
Russian Federation, Volgograd

G. M. Butov

Volgograd state technical university (VSTU); Volzhsky polytechnic institute (branch) VSTU

Email: butov@post.volpi.ru
Russian Federation, Volgograd; Volzhsky

References

  1. Данилов Д.В., Дьяченко В.С., Бурмистров В.В., Бутов Г.М. ЖОрХ, 2022, 58 (11), 1135–1144. [Danilov D.V., D’yachenko V.S., Burmistrov V.V., Butov G.M. Russ. J. Org. Chem. 2022, 58 (11), 1561-1568.] doi. 10.31857/S0514749222110015
  2. Niu Tianyu, Zhao Xiaoqiang, Jiang Jing, Yan Haiyan, Li Yinghong, Tang Sheng, Li Yuhuan, Song Danqing Molecules. 2019, 24 (5), 921. doi: 10.3390/molecules24050921
  3. Park Jin-Hee, Lee Ga-Eun, Lee So-Deok, Hien Tran Thi, Kim Sujin, Yang Jin Won, Cho Joong-Heui, Kang Keon-Wook, Kim Yong-Chul. J. Med.Chem. 2015, 58 (5), 2114–2134. doi: 10.1021/jm2012326
  4. Telfer T.J., Liddell J.R., Duncan C., White A.R., Codd R. Bioorg. Med. Chem. Lett. 2017, 27 (8), 1698 – 1704. doi: 10.1016/j.bmcl.2017.03.001
  5. Hwang S.H., Wecksler A.T., Zhang G., Morisseau C., Nguyen L.V., Fu S.H., Hammock B.D., Bioorg. Med. Chem. Lett. 2013, 23, 3732–3737. doi: 10.1016/j.bmcl.2013.05.011
  6. Wagner K.M., McReynolds C.B., Schmidt W.K., Hammock B.D. Pharmacol. Ther. 2017, 180, 62–76. doi: 10.1016/j.pharmthera.2017.06.006
  7. Inceoglu B., Jinks S.L., Ulu A., Hegedus C.M., Georgi K., Schmelzer K.R., Wagner K., Jones P.D., Morisseau C., Hammock B.D. Proc. Natl. Acad. Sci. 2008, 105, 18901–18906. doi: 10.1073/pnas.0809765105
  8. 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. ThrombVasc. Biol. 2007, 27, 2612–2618. doi: 10.1161/ATVBAHA.107.152074
  9. Burmistrov V.V., Morisseau C., Harris T.R., Butov G.M., Hammock B.D. Bioorg. Chem. 2018, 76, 510–527. doi: 10.1016/j.bioorg.2017.12.024
  10. Moiseev I.K., Doroshenko R.I., Mratkhuzina T.A., Novikov S.S., USSR Chem. Bull. 1973, 22, 51–54. doi: 10.1007/bf00854113
  11. Burmistrov V., Morisseau C., Lee K.S.S., Shihadih D.S., Harris T.R., Butov G.M., Hammock B.D., Bioorg. Med. Chem. Lett., 2014, 24, 2193. doi: 10.1016/j.bmcl.2014.03.016
  12. Hwang S.H., Wecksler A.T., Zhang G., Morisseau C., Nguyen L.V., Fu S.H., Hammock B.D. Bioorg. Med. Chem. Lett. 2013, 23, 3732. doi: 10.1016/j.bmcl.2013.05.011
  13. Бутов Г.М., Бурмистров В.В., Дьяченко В.С., ЖОрХ, 2017, 53, 965–968. [Butov G.M., Burmistrov V.V., D’yachenko V.S., Russ. J. Org. Chem., 2017, 53, 977–980.] doi: 10.1134/S107042801707003X
  14. Гладких Б.П., Данилов Д.В., Дьяченко В.С., Бурмистров В.В., Бутов Г.М., Новаков И.А. Изв. АН сер. хим. 2022, 9, 1998–2005. [Gladkikh B.P., Danilov D.V., D’yachenko V.S., Burmistrov V.V., Butov G.M., Novakov I.A. Russ. Chem. Bull. (Engl. Transl.), 2022, 9, 1998–2005.] doi: 10.1007/s11172-022-3620-1
  15. Sheldrick G.M., SADABS. Program for Empirical X-ray Absorption Correction, Bruker-Nonius, 1990–2004.
  16. Sheldrick, G.M. Acta Cryst. 2008, A64, 112–122. doi.10.1107/S0108767307043930
  17. Sheldrick, G.M. Acta Cryst. 2015, A71, 3–8. doi: 10.1107/S2053273314026370
  18. Dolomanov O.V., Bourhis L.J., Gildea R.J. J. Appl. Cryst. 2009, 42, 339–341. doi: 10.1107/S0021889808042726

Supplementary files

Supplementary Files
Action
1. JATS XML
Download
2. Fig. 1. Compounds containing 3-bromoadamantyl fragment possessing biological activity

Download (88KB)
Indexing metadata
3. Fig. 2. ORTEP diagram showing the anisotropic displacement ellipsoids of non-hydrogen atoms with a probability of 50% for compound 4k according to the X-ray diffraction data of a single crystal collected at 100 K.

Download (78KB)
Indexing metadata
4. Fig. 3. Dependence of the melting point of halogenated diureas 4a–i on the number of methylene groups n: 1 – F-Ad-(diurea) [14]; 2 – Br-Ad-(diurea); 3 – Cl-Ad-(diurea) [9]

Download (98KB)
Indexing metadata
5. Scheme 1

Download (44KB)
Indexing metadata
6. Scheme 2

Download (190KB)
Indexing metadata
7. Scheme 3

Download (121KB)
Indexing metadata

Copyright (c) 2024 Russian Academy of Sciences