Synthesis and properties of 1,3-disubstituted ureas bearing adamantyl and pyridin(quinolin)yl moieties

Мұқаба

Дәйексөз келтіру

Толық мәтін

Ашық рұқсат Ашық рұқсат
Рұқсат жабық Рұқсат берілді
Рұқсат жабық Рұқсат ақылы немесе тек жазылушылар үшін

Аннотация

A series of 1,3-disubstituted ureas containing pyridine (quinoline) and lipophilic adamantane moieties was synthesized by the reaction of 1,1-dimethyl-3-(hetaryl)ureas with amine hydrochlorides (13 compounds, 53-94% yields). The synthesized compounds differ from each other in the substitution position of the adamantane fragment, the structure of the alkyl linker between the adamantane fragment and the amide group, and the type of heterocyclic substituent. They are potentially targeted inhibitors of human soluble epoxide hydrolase (sEH).

Авторлар туралы

S. Baykova

St Petersburg State University, Institute of Chemistry

S. Baykov

St Petersburg State University, Institute of Chemistry

A. Petrov

St Petersburg State University, Institute of Chemistry

Email: aap1947@yandex.ru

V. Bumistrov

Volgograd State Technical University

V. Boyarskiy

St Petersburg State University, Institute of Chemistry

Email: v.boiarskii@spbu.ru

Әдебиет тізімі

  1. Korkmaz H. SDÜ Tıp Fakültesi Derg. 2021, 28, 171-175. doi: 10.17343/sdutfd.904540
  2. Schopman J.E., Simon A.C.R., Hoefnagel S.J.M, Hoekstra J.B.L., Scholten R.J.P.M., Holleman F. Diabetes Metab. Res. Rev. 2014, 30, 11-22. doi: 10.1002/dmrr.2470
  3. Brown J.R., North E.J., Hurdle J.G., Morisseau C., Scarborough J.S., Sun D., Korduláková J., Scherman M.S., Jones V., Grzegorzewicz A., Crew R.M., Jackson M., McNeil M.R., Lee R.E. Bioorg. Med. Chem. 2011, 19, 5585-5595. doi: 10.1016/j.bmc.2011.07.034
  4. Dorrance A.M., Rupp N., Pollock D.M., Newman J.W., Hammock B.D., Imig J.D. J. Cardiovasc. Pharmacol. 2005, 46, 842-848. doi: 10.1097/01.fjc.0000189600.74157.6d
  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. Hiesinger K., Wagner K.M., Hammock B.D., Proschak E., Hwang S.H. Prostaglandins Other Lipid Mediat. 2019, 140, 31-39. doi: 10.1016/j.prostaglandins.2018.12.003
  7. Imig J.D., Zhao X., Zaharis C.Z., Olearczyk J.J., Pollock D.M., Newman J.W., Kim I.-H., Watanabe T., Hammock B.D. Hypertension. 2005, 46, 975-981. doi: 10.1161/01.HYP.0000176237.74820.75
  8. Das Mahapatra A., Choubey R., Datta B. Molecules. 2020, 25, 5488. doi: 10.3390/molecules25235488
  9. 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
  10. 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
  11. Morisseau C., Hammock B.D. Annu. Rev. Pharmacol. Toxicol. 2013, 53, 37-58. doi: 10.1146/annurev-pharmtox-011112-140244
  12. 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
  13. Wanka L., Iqbal K., Schreiner P.R. Chem. Rev. 2013, 113, 3516-36142. doi: 10.1021/cr100264t
  14. Rassadin V.A., Zimin D.P., Raskil'dina G.Z., Ivanov A.Y, Boyarskiy V.P, Zlotskii S.S., Kukushkin V.Y. Green Chem. 2016, 18, 6630-6636. doi: 10.1039/C6GC02556K
  15. Geyl K., Baykov S., Tarasenko M., Zelenkov L.E, Matveevskaya V., Boyarskiy V.P. Tetrahedron Lett. 2019, 60, 151108. doi: 10.1016/j.tetlet.2019.151108
  16. Kasatkina S.O., Geyl K.K., Baykov S.V., Boyarskaya I.A., Boyarskiy V.P. Org. Biomol. Chem. 2021, 19, 6059-6065. doi: 10.1039/D1OB00783A
  17. Baykov S., Mikherdov A., Novikov A., Geyl K., Tarasenko M., Gureev M., Boyarskiy V. Molecules. 2021, 26, 5672. doi: 10.3390/molecules26185672
  18. Kasatkina S.O., Geyl K.K., Baykov S.V., Novikov M.S., Boyarskiy V.P. Adv. Synth. Catal. 2022, 364, 1295-1304. doi: 10.1002/adsc.202101490
  19. Baykova S.O., Geyl K.K., Baykov S.V., Boyarskiy V.P. Int. J. Mol. Sci. 2023, 24, 7633. doi: 10.3390/ijms24087633
  20. Zhu X., Xu M., Sun J., Guo D., Zhang Y., Zhou S., Wang S. Eur. J. Org. Chem. 2021, 5213-5218. doi: 10.1002/ejoc.202100932
  21. North E.J., Scherman M.S., Bruhn D.F., Scarborough J.S., Maddox M.M., Jones V., Grzegorzewicz A., Yang L., Hess T., Morisseau C., Jackson M., McNeil M.R., Lee R.E. Bioorg. Med. Chem. 2013, 21, 2587-2599. doi: 10.1016/j.bmc.2013.02.028
  22. Abraham R.J., Griffiths L, Perez M. Magn. Reson. Chem. 2014, 52, 395-408. doi: 10.1002/mrc.4079
  23. Molinspiration Chemoinformatic Software, URL: https://www.molinspiration.com
  24. Sheldrick G.M. Acta Crystallogr., Sect. A. 2015, 71, 3-8. doi: 10.1107/S2053273314026370
  25. Sheldrick G.M. Acta Crystallogr., Sect. C. 2015, 71, 3-8. doi: 10.1107/S2053229614024218
  26. Dolomanov O.V., Bourhis L.J., Gildea R.J., Howard J.A.K., Puschmann H. J. Appl. Crystallogr. 2009, 42, 339-341. doi: 10.1107/S0021889808042726

Қосымша файлдар

Қосымша файлдар
Әрекет
1. JATS XML
Жүктеу

© Russian Academy of Sciences, 2023