The povarov reaction in the synthesis of N-polycyclic compounds with a tetrahydroquinoline fragment

Cover Page

Cite item

Full Text

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

Abstract

The review is devoted to the analysis of the data synthesized biologically active tetrahydroquinoline derivatives based on the Povarov reaction and its three-component modification over the past 8 years.

About the authors

R. M Limantseva

Institute of Petrochemistry and Catalysis, Ufa Federal Researcher Centre of the Russian Academy of Sciences

Email: shaki-regina@yandex.ru

R. G Savchenko

Institute of Petrochemistry and Catalysis, Ufa Federal Researcher Centre of the Russian Academy of Sciences

V. N Odinokov

Institute of Petrochemistry and Catalysis, Ufa Federal Researcher Centre of the Russian Academy of Sciences

A. G Tolstikov

Institute of Petrochemistry and Catalysis, Ufa Federal Researcher Centre of the Russian Academy of Sciences

References

  1. Sridharan V., Suryavanshi P.A., Menendez J.C. Chem. Rev. 2011, 111, 7157-7259. doi: 10.1070/RC1967v036n09ABEH001680
  2. Muthukrishnan I., Sridharan V., Menendez J.C. Chem. Rev. 2019, 119, 5057-5191. doi: 10.1021/acs.chemrev.8b00567
  3. Gosmini R., Nguyen V.L., Toum J., Simon C., Brusq J.-M.G., Krysa G., Mirguet O., RiouEymard A.M., Boursier E.V., Trottet L., Bamborough P., Clark H., Chung C.-W., Cutler L., Demont E.H., Kaur R., Lewis A.J., Schilling M.B., Soden P.E., Taylor S., Walker A.L., Walker M.D., Prinjha R.K., Nicodème E. J. Med. Chem. 2014, 57, 8111-8131. doi: 10.1021/jm5010539
  4. Hanashalshahaby E.H.A., Unaleroglu C., Can A.A.K., Ozgun A., Garipcan B. Turk. J. Chem. 2019, 43, 1552-1569. doi: 10.3906/kim-1907-71
  5. Chen C., Zingales S., Wang T., Yuan M., Wang D., Cai L., Jiang Q.J. J. Enzyme Inhib. Med. Chem. 2016, 31, 853-858. doi: 10.3109/14756366.2015.1064120
  6. Dayal N., Wang M., Sintim H.O. ACS Omega. 2020, 5, 23799-23807. doi: 10.1021/acsomega.0c03001
  7. Chavan P., Pansare D.N., Jadhav S., Rai M. Eur. Chem. Bull. 2019, 8, 257-264. doi: 10.17628/ecb.2019.8.257-264
  8. Kumar A., Srivastava S., Gupta G., Chaturvedi V., Sinha S., Srivastava R. ACS Comb. Sci. 2011, 13, 65-71. doi: 10.1021/co100022h
  9. Ozaki T., Sugiyama R., Shimomura M., Nishimura S., Asamizu S., Katsuyama Y., Kakeya H., Onaka H. Org. Biomol. Chem. 2019, 17, 2370-2378. doi: 10.1039/c8ob02846j
  10. Chander S., Ashok P., Zheng Y.-T., Wang P., Raja K.S., Taneja A., Murugesan S. Bioorg. Chem. 2016, 64, 66-73. doi: 10.1016/j.bioorg.2015.12.005
  11. Onyedibe K.I., Dayal N., Sintim H.O. RSC Med. Chem. 2021, 12, 1879-1893. doi: 10.1039/d1md00211b
  12. Diaz G., Miranda I., Sartori S., Dias G., Kohlhoff M., Purgato G., Nogueira M. J. Braz. Chem. Soc. 2018, 29, 2646-2656. doi: 10.21577/0103-5053.20180145
  13. Martínez S., Pavani C., Baptista M., Becerra M., Quevedo M., Ribone S. J. Biomol. Struct. Dyn. 2019, 38, 2412-2421. doi: 10.1080/07391102.2019.1633410
  14. Kimura T., Suga T., Kameoka M., Ueno M., Inahashi Y., Matsuo H., Iwatsuki M., Shigemura K., Shiomi K., Takahashi Y., Ōmura S., Nakashima T. J. Antibiotics. 2019, 72, 169-173. doi: 10.1038/s41429-018-0117-0
  15. Povarov L.S. Russ. Chem. Rev. 1967, 36, 656-670. doi: 10.1070/RC1967v036n09ABEH001680
  16. Глушков В.А., Толстиков А.Г. Усп. хим. 2008, 77, 138-160.
  17. Glushkov V.A., Tolstikov A.G. Russ. Chem. Rev. 2008, 77, 137-159. doi: 10.1070/RC2008v077n02ABEH003749
  18. Ghashghaei O., Masdeu C., Alonso C., Palacios F., Lavilla R. Drug Discov. Today. 2018, 29, 71-79. doi: 10.1016/j.ddtec.2018.08.004
  19. Huang Y., Qiu C., Li Z., Feng W., Gan H., Liu J., Guo K. ACS Sustainable Chem. Eng. 2016, 4, 47-52. doi: 10.1021/ACSSUSCHEMENG.5B01379
  20. Das D.K., Sarkar S., Khan A.T., Saravanan P., Patra S. RSC Adv. 2014, 4, 3581-3590. doi: 10.1039/C3RA45174G
  21. Rai M., Jadhav S., Farooqui M. Orbital Electron. J. Chem. 2016, 8, 149-153. doi: 10.17807/orbital.v8i3.801
  22. DaSilva B.H.S.T., Marana N.L., Mafud A.C., da Silva-Filho L.C. Struct. Chem. 2014, 25, 327-337. doi: 10.1007/s11224-013-0297-y
  23. Puligoundla R.G., Vulupala H.R., Kommu N., Kondra S.B. Synth. Commun. 2015, 45, 494-502. doi: 10.1080/00397911.2014.956366
  24. Cimarelli C., Bordi S., Piermattei P., Pellei M., Del Bello F. Synthesis. 2017, 49, 5387-5395. doi: 10.1055/S-0036-1589104
  25. Sokamisa M.S., Nyondlo Y.M., Kinfe H.H. Arkivoc. 2016, iii, 313-324. doi: 10.3998/ark.5550190.p009.447
  26. Jadhav S., Farooqui M., Chavan P., Hussain S., Rai M. Polycycl. Aromat. Compd. 2020, 1-9. doi: 10.1080/10406638.2020.1825005
  27. Rechac V.L., Cirujano F.G., Corma A., Llabrés F.X. Eur. J. Inorg. Chem. 2016, 27, 4512-4516. doi: 10.1002/ejic.201600372
  28. Da Silva Abranches P.A., de Paiva W.F., de Fátima A., Martins F.T., Fernandes S.A. J. Org. Chem. 2018, 83, 1761-1771. doi: 10.1021/acs.joc.7b02532
  29. de Paiva W.F., Braga I.B., de Assis J.V., Castaneda S.M.B., Sathicq A.G., Palermo V., Romanelli G.P., Natalino R., da Silva M.J., Martins F.T., de Carvalho G.S.G., Amarante G.W., Fernandes S.A. Tetrahedron. 2019, 75, 3740-3750. doi: 10.1016/J.TET.2019.05.049
  30. Rezende T.R.M., Varejão J.O.S., de Almeida Sousa A.L.L., Castañeda S.M.B., Fernandes S.A. Org. Biomol. Chem. 2019, 17, 2913-2922. doi: 10.1039/c8ob02928h
  31. Liua X., Toy P.H. Adv. Synth. Catal. 2020, 362, 3437-3441. doi: 10.1002/adsc.202000665
  32. Reyes-Gutiérrez P.E., Amatov T.T., Švec P., Císařová I., Šaman D., Pohl R., Teplý F., Pospíšil L. Chem. Plus Chem. 2020, 85, 2212-2218. doi: 10.1002/cplu.202000151
  33. Li L.-P., Cai X., Xiang Y., Zhang Y., Song J., Yang D.-C., Guan Z., He Y.-H. Green Chem. 2015, 17, 3148-3156. doi: 10.1039/C4GC01123F
  34. Niño P., Caba M., Aguilar N., Terricabras E., Albericio F., Fernández J.-C. Indian J. Chem. Sect. B. 2016, 55, 1384-1399.
  35. Liu Q., Wang C., Li Q., Hou Y., Wu Y., Liu L., Chang W., Li J. J. Org. Chem. 2017, 82, 950-958. doi: 10.1021/acs.joc.6b02496
  36. Chung P.Y., Tang J.C.O., Cheng C.H., Bian Z.X., Wong W.Y., Lam K.H., Chui C.H. Springer Plus. 2016, 5, 271-276. doi: 10.1186/s40064-016-1890-5
  37. Gurumurthy Ch., Fatima N., Reddy G.N., Kumar C.G., Sabitha G., Ramakrishna K.V.S. Bioorg. Med. Chem. Lett. 2016, 26, 5119-5125. doi: 10.1016/j.bmcl.2016.08.017
  38. Moshapo P.T., Sokamisa M., Mmutlane E.M., Mampa R.M., Kinfe H.H. Org. Biomol. Chem. 2016, 14, 5627-5638. doi: 10.1039/c5ob02536b
  39. Shushizadeh M.R., Mostoufi A., Behfar A., Heidary M. Arabian J. Chem. 2015, 8, 868-872. doi: 10.1016/J.ARABJC.2012.06.007
  40. Yogita M., Ragini G., Ekta M. Int. J. Res. Chem. Environ. 2015, 5, 106-117.
  41. Sanz-Vidal Á., Miró J., Sánchez-Roselló M., del Pozo C., Fustero S. J. Org. Chem. 2016, 81, 6515-6524. doi: 10.1021/acs.joc.6b01139
  42. Arai N., Ohkuma T. J. Org. Chem. 2017, 82, 7628-7636. doi: 10.1021/acs.joc.7b00838
  43. Basavegowda N., Mishra K., Lee Y.R., Joh Y.-G. Bull. Korean Chem. Soc. 2016, 37, 142-147. doi: 10.1002/bkcs/10642
  44. Jha A., Chou T.-Y., AlJaroudi Z., Ellis B.D., Cameron T.S. Beilstein J. Org. Chem. 2014, 10, 848-857. doi: 10.3762/bjoc.10.81
  45. Gatta F., Giudice M., Pomponi M., Marta M. Cheminform. 2010, 2, 174-174. doi: 10.1002/chin.199234174
  46. Gutiérrez M., Arévalo B., Martínez G., Valdés F., Vallejos G., Carmona U., San Martin A. J. Chem. Pharm. Res. 2015, 7, 351-358.
  47. Duarte Y., Dueñas F., Gutiérrez M. J. Chem. Pharm. Res. 2015, 7, 294-299.
  48. Rodríguez Y., Gutiérrez M., Ramírez D., Alzate-Morales J., Bernal C.C., Güiza F.M., Romero-Bohórquez A.R. Chem. Biol. Drug Des. 2016, 88, 498-510. doi: 10.1111/cbdd.12773
  49. Rodriguez Núnez Y.A., Norambuena M., Romero Bohorquez A.R., Morales-Bayuelo A., Gutíerrez M. Heliyon. 2019, 5, 1-7. doi: 10.1016/j.heliyon.2019.e02174
  50. Castillo J.-C., Jiménez E., Portilla J., Insuasty B., Quiroga J., Moreno-Fuquen R., Kennedy A.R., Abonia R. Tetrahedron. 2018, 74, 932-947. doi: 10.1016/j.tet.2017.12.049
  51. Kouznetsov V.V., Merchán-Arenas D.R., Martínez-Bonilla C.A., Macías M.A., Roussel P., Gauthier G.H. J. Braz. Chem. Soc. 2016, 27, 2246-2255. doi: 10.5935/0103-5053.20160117
  52. Bonilla C.A.M., Galvis C.E.P., Méndez L.Y.V, Kouznetsov V.V. RSC Adv. 2016, 6, 37478-37486. doi: 10.1039/C6RA04325A
  53. Bianchini G., Ribelles P., Becerra D., Ramos M.T., Menéndez J.C. Org. Chem. Front. 2016, 3, 412-422. doi: 10.1039/C6QO00037A
  54. Clerigué J., Ramos M.T., Menéndez J.C. Molecules. 2021, 26, 1330-1344. doi: 10.3390/molecules26051330
  55. Van Miert S., Hostyn S., Maes B.U.W., Cimanga K., Brun R., Kaiser M., Mátyus P., Dommisse R., Lemière G., Vlietinck A., Pieters L. J. Nat Prod. 2005, 68, 674-677. doi: 10.1021/np0496284
  56. Sundaram G.S.M., Venkatesh C., Syam Kumar U.K., Ila H., Junjappa H. J. Org. Chem. 2004, 69, 5760-5762. doi: 10.1021/jo049227t
  57. Pasha J., Kandagatla B., Sen S., Kumar Seerapu G.P., Bujji S., Haldar D., Nanduri S., Oruganti S. Tetrahedron Lett. 2015, 56, 2289-2292. doi: 10.1016/j.tetlet.2015.03.078
  58. Makhanya T.R., Gengan R.M., Ata A. Synth. Сommun. 2019, 49, 823-835. doi: 10.1080/00397911.2019.1573373
  59. Suzuki T., Kuwano S., Arai T. Adv. Synth. Catal. 2020, 362, 3208-3212. doi: 10.1002/adsc.202000494
  60. Zanwar M.R., Gawande S.D., Kavala V., Kuo C.-W., Yao C.-F. Adv. Synth. Catal. 2014, 356, 3849-3860. doi: 10.1002/adsc/201400424
  61. Wang H., Wang C., Huang K., Liu L., Chang W., Li J. Org. Lett. 2016, 18, 2367-2370. doi: 10.1021/acs.orglett.6b00804
  62. Cai J., Li F., Deng G.-J., Ji X., Huang H. Green Chem. 2016, 18, 3503-3506. doi: 10.1039/C6GC00779A
  63. Fochi M., Caruana L., Bernardi L. Synthesis. 2014, 46, 135-157. doi: 10.1055/s-0033-1338581
  64. Stevanovic D., Bertuzzi G., Mazzanti A., Fochi M., Bernardi L. Adv. Synth. Catal. 2018, 360, 893-900. doi: 10.1002/ADSC.201701484
  65. Huang D., Xu F., Chen T., Wang Y., Lin X. RSC Adv. 2013, 3, 573-578. doi: 10.1039/C2RA22796G
  66. Yokoi T., Nakagawa Y., Miyagawa H. Pest. Manag. Sci. 2019, 75, 115-124. doi: 10.1002/PS.5160
  67. Kazancioglu M.Z., Kalay E., Kazancioglu E.A., Peshkov V.A. ChemistrySelect. 2019, 4, 8797-8799. doi: 10.1002/slct.201902249
  68. Gelis C., Levitre G., Guerineau V., Touboul D., Neuville L., Masson G. Eur. J. Org. Chem. 2019, 31, 5151-5155. doi: 10.1002/EJOC.201900547
  69. Guo Q., Teng W., Ren S., Rao S., Wang Y., Chen L., Shen B., Takahashi T.J. Heterocycl. Chem. 2014, 51, 1100-1105. doi: 10.1002/JHET.2118
  70. Bunescu A., Wang Q., Zhu J. Org. Lett. 2014, 16, 1756-1759. doi: 10.1021/ol500447r
  71. Cerra B., Mostarda S., Custodi C., Macchiarulo A., Gioiello A. Med. Chem. Comm. 2016, 7, 439-446. doi: 10.1039/C5MD00455A
  72. Niño P., Caba M., Aguilar N., Terricabras E., Albericio F., Fernàndez J.-C. Indian J. Chem., Sect. B. 2016, 55, 854-881. doi: 10.1002/CHIN.201652319
  73. Niño P., Caba M., Aguilar N., Terricabras E., Albericio F., Fernàndez J.-C. Indian J. Chem., Sect. B. 2016, 55, 1117-1130.
  74. Kulkarni A.R., Thakur G.A. Tetrahedron Lett. 2013, 54, 6592-6595. doi: 10.1016/j.tetlet.2013.09.107
  75. Pelit E., Turgut Z. Ultrason. Sonochem. 2014, 21, 1600-1607. doi: 10.1016/j.ultsonch.2014.01.009
  76. Olmos A., Rigolet S., Louis B., Pale P. J. Phys. Chem. C. 2012, 116, 13661-13670. doi: 10.1021/jp303169h
  77. Baumann M. React. Chem. Eng. 2019, 4, 368-371. doi: 10.1039/C8RE00217G
  78. Imrich H.-G., Conrad J., Bubrin D., Beifuss U. J. Org. Chem. 2015, 80, 2319-2332. doi: 10.1021/jo502882y
  79. Petrov V.A. Fluorinated Heterocyclic Compounds: Synthesis, Chemistry, and Applications. New Jersey: John Wiley & Sons, 2009, 1-515. doi: 10.1002/9780470528952
  80. Filler R., Saha R. Future Med. Chem. 2009, 1, 777-791. doi: 10.4155/fmc.09.65
  81. Sharma P.C., Jain A., Jain S. Acta Pol. Pharm. Drug Res. 2009, 66, 587-604.
  82. Tolstikov A.G., Savchenko R.G., Lukina E.S., Nedopekin D.V., Limantceva R.M., Khalilov L.M., Mescheryakova E.S., Odinokov V.N. Helv. Chim. Acta. 2014, 97, 1317-1325. doi: 10.1002/hlca.201300456
  83. Толстиков А.Г., Савченко Р.Г., Лукина Е.С., Недопекин Д.В., Шакирова Р.М., Одиноков В.Н. ЖОрХ. 2014, 50, 136-140.
  84. Tolstikov A.G., Savchenko R.G., Lukina E.S., Nedopekin D.V., Shakirova R.M., Odinokov V.N. Russ. J. Org. Chem. 2014, 50, 128-132. doi: 10.1134/S1070428014010230
  85. Савченко Р.Г., Лиманцева Р.М., Сафарова И.В., Шарипова Г.М., Мещерякова Е.С., Толстиков А.Г., Одиноков В.Н. ЖОрХ. 2022, 58, 188-199.
  86. Savchenko R.G., Limantceva R.M., Safarova I.V., Sharipova G.M., Meshcheriakova E.S., Tolstikov A.G., Odinokov V.N. Russ. J. Org. Chem. 2022, 58, 188-199. doi: 10.31857/s0514749222020100
  87. Толстиков А.Г., Савченко Р.Г., Лукина Е.C., Лиманцева Р.М., Одиноков В.Н. Изв. Акад. наук. Сер. хим. 2014, 63, 2077-2080.
  88. Tolstikov A.G., Savchenko R.G., Lukina E.S., Limantseva R.M., Odinokov V.N. Russ. Chem. Bull. 2014, 63, 2077-2080. doi: 10.1007/s11172-014-0704-6
  89. Mellor J.M., Merriman G.D., Riviere P. Tetrahedron Lett. 1991, 32, 7103-7106. doi: 10.1016/0040-4039(91)85052-7
  90. Tolstikov A.G., Savchenko R.G., Lukina E.S., Limantceva R.M., Nedopekin D.V., Khalilov L.M., Mescheryakova E.S., Odinokov V.N. Synthesis. 2015, 47, 2467-2472. doi: 10.1055/s-0034-1380696
  91. Savchenko R.G., Limantceva R.M., Khursan S.L., Mescheryakova E.S., Tolstikov A.G., Odinokov V.N. J. Heterocycl. Chem. 2022, 59, 20225-2036. doi.org/10.1002/jhet.4540
  92. Benmeddah A., Bar N., Villemin D., Lohier J.-F., Mostefa-Kara B., Legay R. Helv. Chim. Acta. 2018, 101, e1800023. doi: 10.1002/HLCA.201800023
  93. Stepakov A.V., Boitsov V.M., Larina A.G., Molchanov A.P. Russ. J. Org. Chem. 2014, 50, 389-393. doi: 10.1134/S1070428014030154
  94. Saranya S., Baiju T.V., Gopalan G., Radhakrishnan K.V. Synth. Comm. 2018, 48, 816-829. doi: 10.1080/00397911.2018.1427270
  95. Priestley E.S., De Lucca I., Zhou J., Saiah E., Stanton R., Robinson L., Luettgen J.M., Wei A., Wen X., Knabb R.M., Wong P.C., Wexler R.R. Bioorg. Med. Chem. Lett. 2013, 23, 2432-2435. doi: 10.1016/j.bmcl.2013.02.013
  96. Alonso C., Fuertes M., González M., Rubiales G., Tesauro C., Knudsen B.R., Palacios F. Eur. J. Med. Chem. 2016, 115, 179-190. doi: 10.1016/j.ejmech.2016.03.031
  97. Mohinuddin P.Md.K., Dada R., Almansour A.I., Arumugam N., Yaragorla S. Tetrahedron Lett. 2019, 60, 1043-1048. doi: 10.1016/j.tetlet.2019.03.021
  98. Arenas D.R.M., Kouznetsov V.V. J. Org. Chem. 2014, 79, 5327-5333. doi: 10.1021/jo500516c
  99. Merchan-Arenas D.R., Sojo F., Arvelo F., Kouznetsov V.V. RSC Adv. 2020, 10, 42287-42296. doi: 10.1039/d0ra04555a
  100. Kouznetsov V.V., Merchán-Arenas D., Tangarife-Castaño V., Correa-Royero J., Betancur-Galvis L. Med. Chem. Res. 2016, 25, 429-437. doi: 10.1007/s00044-015-1486-6
  101. Nair P.P.S., Chandrashekarappa K.K.H., Masagalli J.N., Nagaraja P., Mahadevan K.M. Int. J. Pharm. Pharmaceut. Sci. 2015, 7, 448-459.
  102. Forero J.S.B., de Carvalho E.M., Jones J.Jr., da Silva F.M. Curr. Org. Synth. 2015, 12, 102-107. doi: 10.2174/1570179411666140722175810
  103. Romero-Bohórquez A.R., Kouznetsov V.V., Zacchino S.A. Univ. Sci. 2014, 20, 177-189. doi: 10.11144/Javeriana.SC20-2.siea
  104. Bohórquez A.R.R., Romero-Daza J., Acelas M. Synth. Commun. 2016, 46, 338-347. doi: 10.1080/00397911.2015.1136646
  105. Tan Y.-J., Zhang Z., Wang F.-J., Wu H.-H., Li Q.-H. RSC Adv. 2014, 4, 35635-35638. doi: 10.1039/C4RA05252H
  106. Kaboudin B., Sohrabi M., Kazemi F. J. Heterocycl. Chem. 2021, 58, 1594-1600. doi: 10.1002/jhet.4283
  107. Alonso C., Martin-Encinas E., Rubiales G., Palacios F. Eur. J. Org. Chem. 2017, 2017, 2916-2924. doi: 10.1002/EJOC.201700258
  108. Huang L., Chen J.-P., Jin C., Su W.-K. Chin. Chem. Lett. 2013, 24, 347-350.
  109. Yin D.H., Liu W., Wang Z.X., Huang X., Zhang J., Huang D.C. Chin. Chem. Lett. 2017, 28, 153-158. doi: 10.1016/j.cclet.2016.10.015

Supplementary files

Supplementary Files
Action
1. JATS XML
Download

Copyright (c) 2023 Russian Academy of Sciences