Synthesis, chemocal properties and application of 2-substituted derivatives of thiazolo[3,2-a]pyrimidine

Мұқаба

Дәйексөз келтіру

Толық мәтін

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

Аннотация

The review describes in detail the methods of obtaining thiazolo[3,2- a ]pyrimidines, synthesis and chemical properties of 2-substituted derivatives of thiazolo[3,2- a ]pyrimidines, analysis of crystal structures of 2-arylmethylidene derivatives of thiazolo[3,2- a ]pyrimidines and demonstrates their high antitumor, antibacterial and anti-inflammatory activity.

Авторлар туралы

A. Agarkov

Arbuzov Institute of Organic and Physical Chemistry, Kazan Research Centre, Russian Academy of Sciences

Email: artem.agarkov.95.chem@mail.ru

A. Shiryaev

Samara State Technical University

Email: artem.agarkov.95.chem@mail.ru

S. Solovieva

Arbuzov Institute of Organic and Physical Chemistry, Kazan Research Centre, Russian Academy of Sciences

Email: artem.agarkov.95.chem@mail.ru

I. Antipin

Kazan Federal University

Email: artem.agarkov.95.chem@mail.ru

Әдебиет тізімі

  1. Keshari A.K., Singh A.K., Saha S. Mini-Rev. Med. Chem. 2017, 17, 1488-1499. doi: 10.2174/1389557517666170216142113
  2. Kashyap S.J., Sharma P.K., Garg V.K., Dudhe R., Kumar N. J. Adv. Sci. Res. 2011, 2, 18-24. doi: 10.1002/chin.201209270
  3. Chen L., Jin Y., Fu W., Xiao S., Feng C., Fang B., u Y., Li C., Zhao Y., Liu Z., Liang G. ChemMedChem. 2017, 12, 1022-1032 doi: 10.1002/cmdc.201700175
  4. Zhi H., Chen L.M., Zhang L.L., Liu S.J., Wan D.C.C., Lin H.Q., Hu C. Arkivoc. 2008, 13, 266. doi: 10.3998/ark.5550190.0009.d29
  5. Quan Z.J., Zhang Z., Wang J.K., Wang X.C., Liu Y.J., Ji P.Y. Heteroat. Chem. 2008, 2, 149. doi: 10.1002/hc.20386
  6. Wichmann J., Adam G., Kolczewski S., Mutel V., Woltering T. Bioorg. Med. Chem. Lett. 1999, 9, 1573. doi: 10.1016/S0960-894X(99)00227-9
  7. Danel K., Pedersen E.B., Nielsen C. J. Med. Chem. 1998, 41, 191. doi: 10.1021/jm970443m
  8. Pan B., Huang R., Zheng L., Chen C., Han S., Qub D., Zhu M., Wei P. Eur. J. Med. Chem. 2011, 46, 819-824. doi: 10.1016/j.ejmech.2010.12.014
  9. Mohamed S.F., Flefel E.M., Amra A.E., Abd El-Shafy D.N. Eur. J. Med. Chem. 2012, 45, 1494-1501. doi: 10.1016/j.ejmech.2009.12.057
  10. Rashad A.E., Sayed H.H., Shamroukh A.H., Awad H.M. hosphorus, Sulfur Silicon Relat. Elem. 2005, 180, 2767. doi: 10.1080/104265090968118
  11. Kolb S., Mondesert O., Goddard M.-L., Jullien D., Villoutreix B.O., Ducommun B., Garbay C., Braud E. hem. Med. Chem. 2009, 4, 633. doi: 10.1002/cmdc.200800415
  12. Ghorab M.M., Mohamad Y.A., Mohamed S.A., Ammar Y.A. Phosphorus, Sulfur Silicon Relat. Elem. 1996, 108, 249-256. doi: 10.1080/10426509608029657
  13. Singh S., Schober A., Gebinoga M., Groß G.A. Tetrahedron Lett. 2011, 52, 3814. doi: 10.1016/j.tetlet.2011.05.067
  14. Sekhar T., Thriveni P., Venkateswarlu A., Daveedu T., Peddanna K., Sainath S.B. Spectrochim. Acta A. Mol. Biomol. Spectrosc. 2020, 231, 118056. doi: 10.1016/j.saa.2020.118056
  15. Kulakov I.V., Nurkenov O.A., Turdybekov D.M., Issabaeva G.M., Mahmutova A.S., Turdybekov K.M. Chem. Heterocyc. Compd. 2009, 45, 856-859. doi: 10.1007/s10593-009-0346-z
  16. Ширяев А.К., Колесникова Н.Г., Кузнецова Н.М., Лашманова Е.А. ХГС. 2013, 49, 1812-1817. doi: 10.1007/s10593-014-1420-8
  17. Shiryaev A.K., Baranovskaya N.S., Eremin M.S. Chem. Heterocycl. Compd. 2013, 48, 1550-1554. doi: 10.1007/s10593-013-1172-x
  18. Xiao D., Han L., Sun Q., Chen Q., Gong N., Lv Y., Suzenet F., Guillaumet G., Cheng T., Li R. RSC Adv. 2012, 2, 5054-5057. doi: 10.1039/C2RA20254A
  19. Shelke A.V., Bhong B.Y., Karade N.N. Tetrahedron Lett. 2013, 54, 600-603. doi: 10.1016/j.tetlet.2012.11.098
  20. Castagnolo D., Pagano M., Bernardini M., Botta M. Synlett. 2009, 2009, 2093-2096. doi: 10.1055/s-0029-1217700
  21. Khalilpour A., Asghari S., Pourshab M. Chem. Biodivers. 2019, 16, e1800563. doi: 10.1002/cbdv.201800563
  22. Tozkoparan B., Ertan M., Krebs B., Läge M., Kelicen P., Demirdamar R. Arch. Pharm. 1998, 331, 201-206. doi: 10.1002/(SICI)1521-4184(199806)331:6<201::AID-ARDP201>3.0.CO;2-T
  23. Lashmanova E.A., Kirdyashkina A.I., Slepukhin P.A., Shiryaev A.K. Tetrahedron Lett. 2018, 59, 1099-1103. doi: 10.1016/j.tetlet.2018.02.014
  24. Sherif S.M., Youssef M.M., Mobarak K.M., Abdel-Fattah A.S.M. Tetrahedron. 1993, 49, 9561-9572. doi: 10.1016/S0040-4020(01)80225-8
  25. Lashmanova E.A., Agarkov A.S., Rybakov V.B., Shiryaev A.K. Chem. Heterocycl. Compd. 2019, 55, 1217-1221. doi: 10.1007/s10593-019-02604-4
  26. Агарков А.С., Коноров Г.В., Нефедова А.А., Габитова Э.Р., Исламов Д.Р., Овсянников А.С., Ширяев А.К., Соловьева С.Е., Антипин И.С. Бутлеров. Сообщ. 2021, 68, 122-128. doi: 10.37952/ROI-jbc-01/21-68-10-122
  27. Agarkov A.S., Gabitova E.R., Galieva F.B., Ovsyannikov A.S., Voloshina A.D., Shiryaev A.K., Solovieva S.E., Antipin I.S. Dokl. Chem. 2022, 503, 45-50. doi: 10.1134/S0012500822030016
  28. Лашманова Е.А., Ширяев А.К. Chem. Heterocycl. Compd. 2015, 51, 377-380. doi: 10.1007/s10593-015-1710-9
  29. Nagarajaiah H., Khazi I.A.M., Begum N.S. J. Chem. Sci. 2015, 127, 467-479. doi: 10.1007/s12039-015-0797-y
  30. Lebedyeva I.O., Povstyanoy M.V., Ryabitskii A.B., Povstyanoya V.M. J. Heterocycl. Chem. 2010, 47, 368-372. doi: 10.1002/jhet.323
  31. Alam O., Khan S.A., Siddiqui N., Ahsan W. Med. Chem. Res. 2010, 19, 1245-1258. doi: 10.1007/s00044-009-9267-8
  32. Hu J., Wang Y., Wei X., Wu X., Chen G., Cao G., Li X. Eur. J. Med. Chem. 2013, 64, 292-301. doi: 10.1016/j.ejmech.2013.04.010
  33. Kotaiah Y., Krishna N.H., Raju K.N., Rao C.V., Jonnalagadda S.B., Maddila S. J. Korean Chem. Soc. 2012, 56, 68-73. doi: 10.5012/jkcs.2012.56.1.068
  34. Alzahrani H.E., Fouda A.M., Youssef A.M. J. Chin. Chem. Soc. 2020, 67, 838-855. doi: 10.1002/jccs.201900199
  35. Liu X.G., Feng Y.Q., Li X.F., Liang Z.P. Acta Crystallogr., Sect. E. 2004, 60, 344-345. doi: 10.1107/S1600536804002740
  36. Jotani M.M., Baldaniya B.B. Acta Crystallogr., Sect. E. 2006, 62, 5871-5873. doi: 10.1107/S1600536806050379
  37. Jotani M.M., Baldaniya B.B., Jasinski J.P. J. Chem. Crystallogr. 2009, 39, 898-901. doi: 10.1007/s10870-009-9587-z
  38. Jotani M.M., Baldaniya B.B. Acta Crystallogr., Sect. E. 2008, 64, 739. doi: 10.1107/S1600536808007356
  39. Liu X.G., Feng Y.Q., Li X.F., Gao B. Acta Crystallogr., Sect. E. 2004, 60, 464-465. doi: 10.1107/S1600536804004143
  40. Banu N.A., Raju V.B. Acta Crystallogr., Sect. E. 2012, 68, 441. doi: 10.1107/S1600536812000050
  41. Hou Z.H., Zhou N.B., He B.H., Li X.F. Acta Crystallogr., Sect. E. 2009, 65, 375. doi: 10.1107/S1600536809002451
  42. Jotani M.M., Baldaniya B.B., Tiekink E.R. Acta Crystallogr., Sect. E. 2010, 66, 762-763. doi: 10.1107/S1600536810007853
  43. Baldaniya B.B., Jotani M.M. Anal. Sci. X-ray Struct. Anal. Online. 2008, 24, 217-218. doi: 10.2116/analscix.24.x217
  44. Hou Z.H. Acta Crystallogr., Sect. E. 2009, 65, 235. doi: 10.1107/S1600536808041019
  45. Krishnamurthy M.S., Nagarajaiah H., Begum N.S. Acta Crystallogr., Sect. E. 2014, 70, 1187-1188. doi: 10.1107/S1600536814023010
  46. Jotani M.M., Baldaniya B.B., Jasinski J.P. Acta Crystallogr., Sect E. 2010, 66, 599-600. doi: 10.1107/S1600536810004812
  47. Nagarajaiah H., Begum N.S. J. Chem. Sci. 2014, 126, 1347-1356. doi: 10.1007/s12039-014-0694-9
  48. Chen X.Y., Wang H.C., Zhang Q., Song Z.J., Zheng F.Y. Acta Crystallogr., Sect. E. 2012, 68, 127. doi: 10.1107/S1600536811052925
  49. Hu J., Wu X.X., Shen X.Q., Tang L.G., Li X.K. Acta Crystallogr., Sect E. 2012, 68, 3099. doi: 10.1107/S1600536812041748
  50. Fischer A., Yathirajan H.S., Mithun A., Bindya S., Narayana B. Acta Crystallogr., Sect. E. 2007, 63, 1224-1225. doi: 10.2174/1389557517666170216142113
  51. Jotani M.M., Baldaniya B.B. Acta Crystallogr., Sect E. 2007, 63, 1937-1939. doi: 10.1107/S1600536807012731
  52. Zhao C.G., Hu J., Zhang Y.L., Zhang J., Yang S.L. Acta Crystallogr., Sect. E. 2011, 67, 3009. doi /10.1107/S1600536811042899
  53. Banu N.A., Bheema Raju V. Acta Crystallogr., Sect E. 2012, 68, 1213. doi: 10.1107/S1600536812012354
  54. Krishnamurthy M.S., Begum N.S. Acta Crystallogr., Sect E. 2014, 70, 1270-1271. doi: 10.1107/S1600536814025008
  55. Geist J.G., Lauw S., Illarionova V., Illarionov B., Fischer M., Gräwert T., Diederich F. ChemMedChem. 2010, 5, 1092-1101. doi: 10.1002/cmdc.201000083
  56. Agarkov A.S., Litvinov I.A., Gabitova E.R., Ovsyannikov A.S., Dorovatovskii P.V., Shiryaev A.K., Solovieva S.E., Antipin I.S. Crystals. 2022, 12, 494. doi: 10.3390/cryst12040494
  57. Abdel-Gawad S.M., El-Gaby M.S., Ghorab M.M. Farmaco. 2000, 55, 287-292. doi: 10.1016/S0014-827X(00)00042-2
  58. Wenlin X., Liangkun J., Yiqiang W., Yanfang. Y. Пат. CN110041349A (2019). Китай.
  59. Li X., Yi P., Yu X. Chin. J. Chem. 2010, 28, 97-101. doi: 10.1002/CHIN.201020136
  60. Agarkov A.S., Kozhikhov A.A., Nefedova A.A., Ovsyannikov A.S., Islamov D.R., Solovieva S.E., Antipin I.S. Dokl. Chem. 2022, 505, 177-183. doi: 10.1134/S0012500822700070
  61. Nagaraju P., Reddy P.N., Padmaja P., Ugale V.G. Lett. Org. Chem. 2021, 18, 49-57. doi: 10.2174/1570178617999200517130138
  62. El-Shahat M., Salama M., El-Farargy A.F., Ali M.M., Ahmed D.M. Mini Rev. Med. Chem. 2021, 21, 118-131. doi: 10.2174/1389557520666200619182519
  63. Sukanya S.H., Venkatesh T., Rao S.A., Joy M.N. J Mol. Struct. 2022, 1247, 131324. doi: 10.1016/j.molstruc.2021.131324
  64. Nagaraju P., Reddy P.N., Padmaja P., Ugale V.G. Lett. Org. Chem. 2020, 17, 951-958. doi: 10.2174/1570178617666200319114611
  65. Mohamed S.F., Abbas E.M., Khalaf H.S., Fargha-ly T.A., Abd El-Shafy D.N. Mini Rev. Med. Chem. 2018, 18, 794-802. doi: 10.2174/1389557518666171207161542
  66. Abdel-Hafez N.A., Mohamed S.F., El-Hag F.A., awas U.W., Awad H.M. Der Pharma Chem. 2016, 8, 1-10. doi: 10.1134/S1070363217100218
  67. Kajal A., Bala S., Sharma N., Kamboj S., Saini V. nt. J. Med. Chem. 2014, 2014, 69-75. doi: 10.1155/2014/191072
  68. Studzińska R., Kołodziejska R., Redka M., Modzelewska-Banachiewicz B., Augustyńska B. J. Braz. Chem. Soc. 2016, 27, 1587-1593 doi: 10.5935/0103-5053.20160038
  69. Gali R., Banothu J., Porika M., Velpula R., Hnamte S., Bavantula R., Busi S. Bioorg. Med. Chem. Lett. 2014, 24, 4239-4242. doi: 10.1016/j.bmcl.2014.07.030
  70. Zhou B., Li X., Li Y., Xu Y., Zhang Z., Zhou M., ang R. ChemMedChem. 2011, 6, 904-921. doi: 10.1002/cmdc.201000484
  71. Feng Y., Ding X., Chen T., Chen L., Liu F., Jia X., ang H. J. Med. Chem. 2010, 53, 3465-3479. doi: 10.1021/jm901004c
  72. Jin C.H., Jun K.Y., Lee E., Kim S., Kwon Y., Kim K., Na Y. Bioorg. Med. Chem. 2014, 22, 4553-4565. doi: 10.1016/j.bmc.2014.07.037
  73. Volgraf M., Sellers B.D., Jiang Y., Wu G., Ly C.Q., Villemure E., Schwarz J.B. J. Med. Chem. 2016, 59, 2760-2779. doi: 10.1021/acs.jmedchem.5b02010
  74. Basiony E.A., Hassan A.A. Molecules. 2020, 25, 399. doi: 10.3390/molecules25020399
  75. Basiri A., Xiao M., McCarthy A., Dutta D., Byrareddy S.N., Conda-Sheridan M. Bioorg. Med. Chem. Lett. 2017, 27, 228-231. doi: 10.1016/j.bmcl.2016.11.065
  76. Shahid Nadeem M., Azam Khan J., Kazmi I., ashid U. ACS Omega. 2022, 7, 9369-9379. doi: 10.1021/acsomega.1c06344
  77. Istanbullu H., Bayraktar G., Akbaba H., Cavus I., Coban G., Debelec Butuner B., Erciyas E. Arch. Pharm. 2020, 353, 1900325. doi: 10.1002/ardp.201900325
  78. Afradi M., Foroughifar N., Pasdar H., Moghanian H., Foroughifar N. Appl Organomet Chem. 2017, 31, e3683. doi: 10.1002/aoc.3683
  79. Moty S.G.A., Hussein M.A., Aziz S.A.A., Abou-Salim M.A. Saudi Pharm. J. 2016, 24, 119-132. doi: 10.1016/j.jsps.2013.12.016
  80. Abdelghani E., Said S.A., Assy M.G., Abdel Hamid A.M. J. Iran. Chem. Soc. 2015, 12, 1809-1817. doi: 10.1007/s13738-015-0656-2
  81. Hamouda A.M. Der Pharma Chem. 2014, 6, 346-357.
  82. Mohamed M.M., Khalil A.K., Abbass E.M., El-Naggar A.M. Synth. Commun. 2017, 47, 1441-1457. doi: 10.1080/00397911.2017.1332223
  83. Cai D., Zhang Z.H., Chen Y., Yan X.J., Zhang S.T., Zou L.J., Fu B. Med. Chem. Res. 2016, 25, 292-302. doi: 10.1007/s00044-015-1481-y
  84. Batool I., Saeed A., Qureshi I.Z., Kalsoom S., Razzaq A. Res. Chem. Intermed. 2016, 42, 1139-1163. doi: 10.1007/s11164-015-2078-2
  85. Banoth S., Boda S., Perugu S., Balabadra S., Manga V. Res. Chem. Intermed. 2018, 44, 1833-1846. doi: 10.1007/s11164-015-2078-2

Қосымша файлдар

Қосымша файлдар
Әрекет
1. JATS XML
Жүктеу

© Russian Academy of Sciences, 2023