Synthesis of fluoroalkyl and fluoroaryl substituted hexahydropyrimidines

Мұқаба

Дәйексөз келтіру

Толық мәтін

Ашық рұқсат Ашық рұқсат
Рұқсат жабық Рұқсат берілді
Рұқсат жабық Тек жазылушылар үшін

Аннотация

The data on the synthesis of fluoroalkyl and fluoroaryl substituted hexahydropyrimidine derivatives from the moment of their first mention are systematized. Predominantly one-pot multicomponent synthesis methods, including catalytic ones, are considered. The effect of the nature of the catalyst, starting reagents, and synthesis conditions on the yield and composition of the resulting products is discussed, and the biological activity of some derivatives is also shown.

Авторлар туралы

N. Gibadullina

Ufa Institute of Chemistry - Subdivision of the Ufa Federal Research Centre of the Russian Academy of Sciences

Email: hetcom@anrb.ru

V. Dokichev

Ufa Institute of Chemistry - Subdivision of the Ufa Federal Research Centre of the Russian Academy of Sciences

Email: hetcom@anrb.ru

Әдебиет тізімі

  1. Liu S.-W., Jin J., Chen C., Liu J.-M., Li J.-Y., Wang F.-F., Jiang Z.-K., Hu J.-H., Gao Z.-X., Yao F., You X.-F., Si S.-Y., Sun C.-H. J. Antibiot. 2013, 66, 281-284. doi: 10.1038/ja.2012.118
  2. Bisceglia J.А., Garcia M.B., Massa R., Magria M.L., Zani M., Gutkind G.O., Orelli L.R. J. Heterocycl. Chem. 2004, 41, 85-90. doi: 10.1002/jhet.5570410113
  3. Киреева Д.Р., Зилеева З.Р., Ишметова Д.В., Докичев В.А. ЖОрХ. 2021, 57, 1036-1041.
  4. Kireeva D.R., Dokichev V.A., Zileeva Z.R., Ishmetova D.V. Russ. J. Org. Chem. 2021, 57, 1180-1183. doi: 10.31857/S0514749221070156
  5. Latypova D.R., Badamshin A.G., Gibadullina N.N., Khusnutdinova N.S., Zainullina L.F., Vakhitova Yu.V., Tomilov Yu.V., Dokichev V.A. Med. Chem. Res. 2017, 26, 900-908. doi: 10.1007/s00044-017-1802-4
  6. Shakirov R.R., Yarmukhamedov N.N., Vlasova L.I., Baibulatova N.Z., Khisamutdinova R.Yu., Gabdrakhmanova S.F., Karachurina L.T., Baschenko N.Zh. Pharm. Chem. J. 2006, 40, 29-31. doi: 10.1007/s11094-006-0051-5
  7. Hwang J.Y., Kim H.-Y., Jo S., Park E., Choi J., Kong S., Park D.-S., Heo J.M., Lee J.S., Ko Y., Choi I., Cechetto J., Kim J., Lee J., No Z., Windisch M.P. Eur. J. Med. Chem. 2013, 70, 315-325. doi: 10.1016/j.ejmech.2013.09.055
  8. Martins F.J., Caneschi C.A., Senra M.P., Carvalho G.S.G., da Silva A.D., Raposo N.R.B. Sci. World J. 2017, 2017, 1207061. doi: 10.1155/2017/1207061
  9. Sabnis R. W. ACS Med. Chem. Lett. 2021, 12, 679-680. doi: 10.1021/acsmedchemlett.1c00171
  10. Kang T., Gao Sh., Zhao L.-X., Zhai Yu., Ye F., Fu Y. J. Agric. Food Chem. 2021, 69, 45-54. doi: 10.1021/acs.jafc.0c04436
  11. Sapozhnikova T.A., Borisevich S.S., Kireeva D.R., Gabdrakhmanova S.F., Khisamutdinova R.Yu., Makara N.S., Gibadullina N.N., Khursan S.L., Zarudii F.S. Behav. Brain Res. 2019, 373, 112109. doi: 10.1016/j.bbr.2019.112109
  12. Organofluorine Chemicals and Their Industrial Applications. Eds. R. Filler, R.E. Banks. Chichester: Ellis Horwood Ltd, 1979.
  13. Fluorine and Health: Molecular Imaging, Biomedical Materials and Pharmaceuticals. Eds. A. Tressaud, G. Haufe. Amsterdam: Elsevier Science Ltd., 2008.
  14. Purser S., Moore P.R., Swallow S., Gouverneur V. Chem. Soc. Rev. 2008, 37. 320-330. doi: 10.1039/B610213C
  15. Wang J., Sanchez-Rosello M., Acena J.L., Pozo C.D., Sorochinsky A.E., Fustero S., Soloshonok V.A., Liu H. Chem. Rev. 2014, 114, 2432-2506. doi: 10.1021/cr4002879
  16. Sedgwick D.M., Roman R., Barrio P., Trabanco A.A., Fustero S. Fluorine in Life Sciences: Pharmaceuticals, Medicinal Diagnostics, and Agrochemicals. Eds. G. Haufe, F.R. Leroux. San Diego: Academic Press. 2019, 575-606. doi: 10.1016/B978-0-12-812733-9.00016-7
  17. Choi P.J., Lu G.-L., Sutherland H.S., Giddens A.C., Franzblau S.G., Cooper Ch.B., Denny W.A., Palmer B.D. Tetrahedron Lett. 2022, 90, 153611. doi: 10.1016/j.tetlet.2021.153611
  18. Agbaje O.C., Fadeyi O.O., Fadeyi S.A., Myles L.E., Okoro C.O. Bioorg. Med. Chem. Lett. 2011, 21, 989-992. doi: 10.1016/j.bmcl.2010.12.022
  19. Zohdi H.F., Rateb N.M., Elnagdy S.M. Eur. J. Med. Chem. 2011, 46, 5636-5640. doi: 10.1016/j.ejmech.2011.09.036
  20. Suresh, Sandhu J.S. Arkivoc. 2012, i, 66-133. doi: 10.3998/ark.5550190.0013.103
  21. Panek D., Wieckowska A., Wichur T., Bajda M., Godyn J., Jonczyk J., Mika K., Janockova J., Soukup O., Knez D., Korabecny J., Gobec S., Malawska B. Eur. J. Med. Chem. 2017, 125, 676-695. doi: 10.1016/j.ejmech.2016.09.078
  22. Multicomponent Reactions. Eds. J. Zhu, H. Bienayme. Weinheim: Wiley-VCH, 2005.
  23. Saloutin V.I., Goryaeva M.V., Kushch S.O., Khudina O.G., Ezhikova M.A., Kodess M.I., Slepukhin P.A., Burgart Ya. V. Pure Appl. Chem. 2020, 92, 1265-1275. doi: 10.1515/pac-2019-1216
  24. Kushch S.O., Goryaeva M.V., Surnina E.A., Burgart Ya.V., Ezhikova M.A., Kodess M.I., Slepukhin P.A., Saloutin V.I. Asian J. Org. Chem. 2022, 11, e202100709. doi: 10.1002/ajoc.202100709
  25. Li Z., Liu Y., Zhang Y., Duan W., Wang Y., Zhang M., Deng H., Song L. J. Fluorine Chem. 2021, 247, 109800. doi: 10.1016/j.jfluchem.2021.109800
  26. Kappe C.O., Falsone S.F. Synlett. 1998, 7, 718-720. doi: 10.1055/s-1998-1764
  27. Kappe C.O., Falsone S.F., Fabian W.M F., Belaj F. Heterocycl. 1999, 51, 77-84. doi: 10.3987/COM-98-8336
  28. Saloutin V.I., Burgart Ya.V., Kuzueva O.G., Kappe C.O., Chupakhin O.N. J. Fluorine Chem. 2000, 103, 17-23. doi: 10.1016/S0022-1139(99)00216-X
  29. Бургарт Я.В., Кузуева О.Г., Прядеина М.В., Каппе К.О., Салутин В. И. ЖОрХ. 2001, 37, 915-926.
  30. Burgart Ya.V., Kuzueva O.G., Pryadeina M.V., Kappe C.O., Saloutin V.I. Russ. J. Org. Chem. 2001, 37, 869-880. doi: 10.1023/A:1012473901354
  31. Кузуева О.Г., Бургарт Я.В., Салоутин В.И., Чупахин О.Н. ХГС. 2001, 37, 1232-1238.
  32. Kuzueva O.G., Burgart Ya.V., Saloutin V.I., Chupakhin O.N. Chem. Heterocycl. Compd. 2001, 37, 1130-1135. doi: 10.1023/A:1013235901570
  33. Путилова Е.С., Троицкий Н.А., Злотин С.Г., Худина О.Г., Бургарт Я.В., Салутин В.И., Чупахин О.Н. ЖОрХ. 2006, 42, 1407-1410.
  34. Putilova E.S., Troitskii N.A., Zlotin S.G., Khudina O.G., Burgart Ya.V., Saloutin V.I., Chupakhin O. N. Russ. J. Org. Chem. 2006, 42, 1392-1395. doi: 10.1134/S1070428006090259
  35. Reddy Ch.V., Mahesh M., Raju P.V.K., Babu T.R., Reddy V.V.N. Tetrahedron Lett. 2002, 43, 2657-2659. doi: 10.1016/S0040-4039(02)00280-0
  36. Bose D.S., Sudharshan M., Chavhan S.W. Arkivoc. 2005, iii, 228-236. doi: 10.3998/ark.5550190.0006.325
  37. Bose D.S., Chary M.V., Mereyala H.B. Heterocycl. 2006, 68, 1217-1224. doi: 10.3987/COM-06-10706
  38. Bose D.S., Idrees M. J. Heterocycl. Chem. 2007, 44, 211-214. doi: 10.1002/jhet.5570440133
  39. Sabitha G., Reddy G.S.K.K., Reddy Ch.S., Yadav J.S. Synlett. 2003, 6, 858-860. doi: 10.1055/S-2003-38734
  40. Ryabukhin S.V., Plaskon A.S., Ostapchuk E.N., Volochnyuk D.M., Shishkin O.V., Tolmachev A.A. J. Fluorine Chem. 2008, 129, 625-631. doi: 10.1016/j.jfluchem.2008.05.004
  41. Zhu L., Cheng P., Lei N., Yao J., Sheng Ch., Zhuang Ch., Guo W., Liu W., Zhang Yo., Dong G., Wang Sh., Miao Zh., Zhang W. Arch. Pharm. Chem. Life Sci. 2011, 344, 726-734. doi: 10.1002/ardp.201000402
  42. Khunt R.C., Akbari J.D., Manvar A.T., Tala S.D., Dhaduk M.F., Joshi H.S., Shah A. Arkivoc. 2008, xi, 277-284. 10.3998/ark.5550190.0009.b27
  43. Azizian J., Mirza B., Mojtahedi M.M., Abaee M.S., Sargordan M. J. Fluorine Chem. 2008. 129, 1083-1089. doi: 10.1016/j.jfluchem.2008.06.025
  44. Chen Q., Jiang L.-L., Chen Ch.-N., Yang G.-F. J. Heterocycl. Chem. 2009, 46, 139-148. doi: 10.1002/jhet.1
  45. Martinez J.J., Nope E., Rojas H., Cubillos J., Sathicq A.G., Romanelli G.P. Catal. Lett. 2014, 144, 1322-1331. doi: 10.1007/s10562-014-1267-8
  46. Kappe C.O. J. Org. Chem. 1997, 62, 7201-7204. doi: 10.1021/jo971010u
  47. Sathicq A.G., Ruiz D.M., Constantieux Th., Rodriguez J., Romanelli G.P. Synlett. 2014, 25, 881-883. doi: 10.1055/s-0033-1340845
  48. Palermo V., Sathicq A., Constantieux Th., Rodriguez J., Vazquez P., Romanelli G. Catal. Lett. 2015, 145, 1022-1032. doi: 10.1007/s10562-015-1498-3
  49. Liang-Ce R., Zha Yu., Xia Sh., Ji L., Zhang J., Cai P. J. Heterocycl. Chem. 2016, 53, 56-63. doi: 10.1002/JHET.2299
  50. Kavitha G., Dhandapani A., Gunasekaran B., Suresh M. J. Mol. Struct. 2021, 1228, 129484. doi: 10.1016/j.molstruc.2020.129484
  51. Saraswathi, K., Suresh, M., Pandurangan A. J. Mol. Struct. 2022, 1255, 132447. doi: 10.1016/j.molstruc.2022.132447
  52. Gein V.L., Zamaraeva T.M., Gorgopina E.V., Dmitriev M.V. Chem. Heterocycl. Compd. 2020, 339-346. doi: 10.1007/s10593-020-02665-w
  53. Gibadullina N.N., Latypova D.R., Novikov R.A., Tomilov Y.V., Dokichev V.A. Arkivoc. 2017, iv, 222-235. doi: 10.24820/ark.5550190.p010.003
  54. Gibadullina N.N., Latypova D.R., Vakhitov V.A., Khasanova D.V., Zainullina L.F., Vakhitova Yu.V., Lobov A.N., Ugrak B.I., Tomilov Yu.V., Dokichev V.A. J. Fluorine Chem. 2018, 211, 94-99. doi: 10.1016/j.jfluchem.2018.04.011
  55. Гибадуллина Н.Н. Дис … канд. хим. наук. Уфа. 2021.
  56. Morita Ya., Kamakura R., Takeda M., Yamamoto Yu. Chem. Commun. 1997, 359-360. doi: 10.1039/A608104E
  57. Yan Sh., Chen Yu., Liu L., He N., Lin J. Green Chem. 2010, 12, 2043-2052. doi: 10.1039/C0GC00373E
  58. Solovyev P.A., Fesenko A.A., Shutalev A.D. J. Fluorine Chem. 2016, 182, 28-33. doi: 10.1016/j.jfluchem.2015.11.008
  59. Qian X., Zhou H., Lakmal H.H.Ch., Lucore J., Wang X., Valle H.U., Donnadieu B., Xu X., Cui X. ACS Catalysis. 2020, 10, 10627-10636. doi: 10.1021/acscatal.0c02676

© Russian Academy of Sciences, 2023

Осы сайт cookie-файлдарды пайдаланады

Біздің сайтты пайдалануды жалғастыра отырып, сіз сайттың дұрыс жұмыс істеуін қамтамасыз ететін cookie файлдарын өңдеуге келісім бересіз.< / br>< / br>cookie файлдары туралы< / a>