Advertisement

Synthesis and chemical transformations of 3-acetyl-4-hydroxyquinolin-2(1H)-one and its N-substituted derivatives: bird’s eye view

  • Moaz M. Abdou
  • Zeynel Seferoğlu
  • Mahmoud Fathy
  • Takashiro Akitsu
  • Mamoru Koketsu
  • Ruba Kellow
  • Eric Amigues
Article
  • 69 Downloads

Abstract

The chemistry of 3-acetyl-4-hydroxyquinolin-2(1H)-ones has attracted increased attention in both synthetic organic and medicinal chemistry, as numerous advancements in the use of this family of important compounds seems to be of considerable value. This account summarizes the results from the literature focusing on synthesis of 3-acetyl-4-hydroxyquinolin-2(1H)-ones as well as their reactions are also discussed.

Keywords

3-Acetyl-4-hydroxyquinolin-2(1H)-one Synthesis Chemical reactivity Condensation Cyclization Heterocycles 

References

  1. 1.
    I.A. Bessonova, Chem. Nat. Compd. 36, 324 (2000)Google Scholar
  2. 2.
    K. Sharma, S. Khandelwal, R.M. Samarth, M. Kumar, J. Heterocycl. Chem. 53, 220 (2016)CrossRefGoogle Scholar
  3. 3.
    E.A. Clarke, M.F. Grundon, J. Chem. Soc. 438 (1964)Google Scholar
  4. 4.
    M.F. Grundon, Tetrahedron 34, 143 (1978)CrossRefGoogle Scholar
  5. 5.
    V. Vijayakumar, Int. J. Chemtech. Res. 9, 629 (2016)Google Scholar
  6. 6.
    B.T. Ngadjui, J.F. Ayafor, A.N. Bilon, B.L. Sondengam, J.D. Connolly, D.S. Rycroft, Tetrahedron 48, 8711 (1992)CrossRefGoogle Scholar
  7. 7.
    I.V. Ukrainets, N.L. Bereznyakova, E.V. Mospanova, Chem. Heterocycl. Compd. 43, 856 (2007)CrossRefGoogle Scholar
  8. 8.
    E. Lager, P. Andersson, J. Nilsson, I. Pettersson, E. Nielsen, J. Med. Chem. 49, 2526 (2006)PubMedCrossRefGoogle Scholar
  9. 9.
    V. Cecchetti, C. Parolin, S. Moro, T. Pecere, E. Filipponi, A. Calistri, O. Tabarrini, B. Gatto, M. Palumbo, A. Fravolini, T. Giorgio Palu, J. Med. Chem. 43, 3799 (2000)PubMedCrossRefGoogle Scholar
  10. 10.
    M.I. Crespo, J. Gràcia, C. Puig, A. Vega, J. Bou, J. Beleta, T. Doménech, H. Ryder, V. Segarra, J.M. Palacios, Med. Chem. Lett. 10, 2661 (2000)CrossRefGoogle Scholar
  11. 11.
    C.M. Hall, H.G. Johnson, J.B. Wright, J. Med. Chem. 17, 685 (1974)PubMedCrossRefGoogle Scholar
  12. 12.
    Y.F. Suen, L. Robins, B. Yang, A.S. Verkman, M.H. Nantz, M.J. Kurth, Med. Chem. Lett. 16, 537 (2006)CrossRefGoogle Scholar
  13. 13.
    R.V. Davies, D.B. Yates, Prog. Med. Chem. 32, 115 (1995)PubMedCrossRefGoogle Scholar
  14. 14.
    I.V. Ukrainets, S.G. Taran, O.V. Gorokhova, E.A. Taran, N.A. Jaradat, I.Y. Petukhova, Chem. Heterocycl. Compd. 36, 166 (2000)CrossRefGoogle Scholar
  15. 15.
    I.V. Ukrainets, S.G. Taran, P.A. Bezuglyi, S.N. Kovalenko, A.V. Turov, N.A. Marusenko, Chem. Heterocycl. Compd. 29, 1044 (1993)CrossRefGoogle Scholar
  16. 16.
    I.V. Ukrainets, A.A. Tkach, L.Y. Yang, Chem. Heterocycl. Compd. 44, 1347 (2008)CrossRefGoogle Scholar
  17. 17.
    K. Arya, M. Agarwal, Med. Chem. Lett. 17, 86 (2007)CrossRefGoogle Scholar
  18. 18.
    B.S. Jayashree, S. Thomas, Y. Nayak, Med. Chem. Res. 19, 193 (2010)CrossRefGoogle Scholar
  19. 19.
    R. Watpade, A. Bholay, R. Toche, J. Heterocycl. Chem. 54, 3434 (2017)CrossRefGoogle Scholar
  20. 20.
    J.A. Smiley, S.J. Benkovic, J. Am, Chem. Soc. 117, 3877 (1995)CrossRefGoogle Scholar
  21. 21.
    E.J. O’loughlin, G.K. Sims, S.J. Traina, Biodegradation 10, 93 (1999)PubMedCrossRefGoogle Scholar
  22. 22.
    S. Heeb, M.P. Fletcher, S.R. Chhabra, S.P. Diggle, P. Williams, M. Cámara, FEMS Microbiol. Rev. 35, 247 (2011)PubMedCrossRefGoogle Scholar
  23. 23.
    S. Sarveswari, V. Vijayakumar, R. Siva, R. Priya, Appl. Biochem. Biotechnol. 175, 43 (2015)PubMedCrossRefGoogle Scholar
  24. 24.
    M.D. Ferretti, A.T. Neto, A.F. Morel, T.S. Kaufman, E.L. Larghi, Eur. J. Med. Chem. 81, 253 (2014)PubMedCrossRefGoogle Scholar
  25. 25.
    M.A. Ibrahim, H.M. Hassanin, Y.A. Alnamer, Synth. Commun. 44, 3470 (2014)CrossRefGoogle Scholar
  26. 26.
    J.J. Kulagowski, R. Baker, N.R. Curtis, I.M. Mawer, A.M. Moseley, M.P. Ridgill, M. Rowley, I. Stansfield, P.D. Leeson, J. Med. Chem. 37, 1402 (1994)PubMedCrossRefGoogle Scholar
  27. 27.
    N. Dodia, A. Shah, Indian J. Heterocycl. Chem. 9, 139 (1999)Google Scholar
  28. 28.
    M.B. Macedo, R. Kimmel, D. Urankar, M. Gazvoda, A. Peixoto, F. Cools, E. Torfs, L. Verschaeve, E.S. Lima, A. Lyčka, D. Milićević, Eur. J. Med. Chem. 138, 491 (2017)PubMedCrossRefGoogle Scholar
  29. 29.
    C. Zwergel, B. Czepukojc, E. Evain-Bana, Z. Xu, G. Stazi, M. Mori, A. Patsilinakos, A. Mai, B. Botta, R. Ragno, D. Bagrel, Eur. J. Med. Chem. 134, 316 (2017)PubMedCrossRefGoogle Scholar
  30. 30.
    Y.F. Chen, Y.C. Lin, S.L. Morris-Natschke, C.F. Wei, T.C. Shen, H.Y. Lin, M.H. Hsu, L.C. Chou, Y. Zhao, S.C. Kuo, K.H. Lee, Br. J. Pharmacol. 172, 1195 (2015)PubMedPubMedCentralCrossRefGoogle Scholar
  31. 31.
    D.A. Sabbaha, B. Hishmaha, K. Sweidana, S. Bardaweelb, M. AlDamenc, G.A. Sheikhaa, M.S. Mubarakc, Anticancer Agents Med. Chem. 18, 263 (2018)CrossRefGoogle Scholar
  32. 32.
    D.A. Sabbah, N.A. Simms, W. Wang, Y. Dong, E.L. Ezell, M.G. Brattain, J.L. Vennerstrom, H.A. Zhong, Bioorg. Med. Chem. 20, 7175 (2012)PubMedCrossRefGoogle Scholar
  33. 33.
    Y. Xia, Z.Y. Yang, P. Xia, T. Hackl, E. Hamel, A. Mauger, J.H. Wu, K.H. Lee, J. Med. Chem. 44, 3932 (2001)PubMedCrossRefGoogle Scholar
  34. 34.
    H.M. Manzoor, M. Ahmad, F.A. Saddique, S. Aslam, S.G. Khan, A. Saddiqa, Afinidad 74, 228 (2017)Google Scholar
  35. 35.
    A. Rivkin, Y.R. Kim, M.T. Goulet, N. Bays, A.D. Hill, I. Kariv, S. Krauss, N. Ginanni, P.R. Strack, N.E. Kohl, C.C. Chung, Bioorg. Med. Chem. Lett. 16, 4620 (2006)PubMedCrossRefGoogle Scholar
  36. 36.
    K.J. Hwang, Arch. Pharmacal Res. 23, 31 (2000)CrossRefGoogle Scholar
  37. 37.
    A.M. MacLeod, S. Grimwood, C. Barton, L. Bristow, K.L. Saywell, G.R. Marshall, R.G. Ball, J. Med. Chem. 38, 2239 (1995)PubMedCrossRefGoogle Scholar
  38. 38.
    M.M. Abdou, New Azo Disperse Dyes Derived from 3-(Hydroxyphenyl)-2-Pyrazolin-5-One, 1st (Lambert Academic Publishing, German Publisher LAP, Riga, 2013), p. 21Google Scholar
  39. 39.
    M.M. Abdou, Azo Disperse Dyes with 2-Pyrazolin-5-Ones for Dyeing Polyester Fabrics, 1st (Lambert Academic Publishing, German Publisher LAP, Riga, 2013), p. 30Google Scholar
  40. 40.
    M.M. Abdou, R.A. El-Saeed, K.M. Elattar, Z. Seferoğlu, J. Boukouvalas, Mol. Divers 20, 989 (2016)PubMedCrossRefGoogle Scholar
  41. 41.
  42. 42.
    M.M. Abdou, A. El Rasha, S. Bondock, Arab. J. Chem. (2015).  https://doi.org/10.1016/j.arabjc.2015.06.029 CrossRefGoogle Scholar
  43. 43.
    M.M. Abdou, Arab. J. Chem. 10, S3955 (2017)CrossRefGoogle Scholar
  44. 44.
    M.M. Abdou, Arab. J. Chem. 10, S3664 (2017)CrossRefGoogle Scholar
  45. 45.
    M.M. Abdou, R.A. El-Saeed, S. Bondock, Arab. J. Chem. (2015).  https://doi.org/10.1016/j.arabjc.2015.06.012 CrossRefGoogle Scholar
  46. 46.
    M.M. Abdou, R.A. El-Saeed, M.A. Abozeid, K.M. Elattar, E.G. Zaki, Y. Barakat, V. Ibrahim, M. Fathy, M. Amine, S. Bondock, Arab. J. Chem. (2015).  https://doi.org/10.1016/j.arabjc.2015.11.004 CrossRefGoogle Scholar
  47. 47.
    M.M. Abdou, Arab. J. Chem. 10, S3324 (2017)CrossRefGoogle Scholar
  48. 48.
    M.M. Abdou, S. Bondock, S.I. El-Desouky, M.A. Metwally, Am. J. Chem. 3, 59 (2013)Google Scholar
  49. 49.
    M.A. Metwally, S. Bondock, E.S.I. El-Desouky, M.M. Abdou, Coloration Technol. 129, 418 (2013)CrossRefGoogle Scholar
  50. 50.
    M.M. Abdou, S. Bondock, S.I. El-Desouky, M.A. Metwally, Int. J. Mod. Org. Chem. 1, 165 (2012)Google Scholar
  51. 51.
    M.M. Abdou, S. Bondock, S.I. El-Desouky, M.A. Metwally, Int. J. Mod. Org. Chem. 1, 19 (2012)Google Scholar
  52. 52.
    M.A. Metwally, S. Bondock, S.I. El-Desouky, M.M. Abdou, J. Korean Chem. Soc. 56, 348 (2012)CrossRefGoogle Scholar
  53. 53.
    M.M. Abdou, S. Bondock, S.I. El-Desouky, M.A. Metwally, Am. J. Chem. 2, 347 (2012)Google Scholar
  54. 54.
    M.A. Metwally, S. Bondock, S.I. El-Desouky, M.M. Abdou, J. Korean Chem. 56, 82 (2012)CrossRefGoogle Scholar
  55. 55.
    W. Stadlbauers, G. Hojas, J. Heterocycl. Chem. 41, 681 (2004)CrossRefGoogle Scholar
  56. 56.
    S. Sarveswari, T.K. Raja, R. Vijayaraghavan, T. Narasimhamurthy, Acta Cryst. E 63, o4600 (2007)CrossRefGoogle Scholar
  57. 57.
    M.M. Hassan, E.S. Othman, M. Abass, Res. Chem. Intermed. 39, 1209 (2013)CrossRefGoogle Scholar
  58. 58.
    A. Detsi, V. Bardakos, J. Markopoulos, O. Igglessi-Markopoulou, J. Chem. Soc. Perkin Trans. 1, 2909 (1996)CrossRefGoogle Scholar
  59. 59.
    T. Kappe, R. Aigner, P. Hohengassner, W. Stadlbauer, Adv. Synth. Catal. 336, 596 (1994)Google Scholar
  60. 60.
    M.A. Ibrahim, H.M. Hassanin, M. Abass, S. Badran, Arkivoc 4, 424 (2013)Google Scholar
  61. 61.
    M. Abass, B.B. Mostafa, Bioorg. Med. Chem. 13, 6133 (2005)PubMedCrossRefGoogle Scholar
  62. 62.
    M.M. Hassan, H.M. Hassanin, J. Heterocycl. Chem. 54, 3321 (2017)CrossRefGoogle Scholar
  63. 63.
    K. Faber, T. Kappe, J. Heterocycl. Chem. 21, 1881 (1984)CrossRefGoogle Scholar
  64. 64.
    I.V. Ukrainets, A.A. Tkach, L.Y. Yang, J. Heterocycl. Chem. 45, 169 (2009)CrossRefGoogle Scholar
  65. 65.
    S.K. Phadtare, S.K. Kamat, G.T. Panse, Indian J. Chem., Sect B 22, 496 (1983)Google Scholar
  66. 66.
    T. Kappe, R. Aigner, P. Roschger, B. Schnell, W. Stadibauer, Tetrahedron 51, 12923 (1995)CrossRefGoogle Scholar
  67. 67.
    M. Abass, H.A. Allimony, H. Hassan, Phosphorus Sulfur Silicon Rel. Elem. 188, 1799 (2013)CrossRefGoogle Scholar
  68. 68.
    P. Roschger, W. Stadlbauer, Eur. J. Org. Chem. 1990, 821 (1990)Google Scholar
  69. 69.
    R.E. Bowman, A. Campbell, E.M. Tanner, J. Chem. Soc. 81, 444 (1959)CrossRefGoogle Scholar
  70. 70.
    T. Razzaq, C.O. Kappe, Tetrahedron Lett. 48, 2513 (2007)CrossRefGoogle Scholar
  71. 71.
    P. Roschger, W. Fiala, W. Stadlbauer, J. Heterocycl. Chem. 29, 225 (1992)CrossRefGoogle Scholar
  72. 72.
    K. Proisl, S. Kafka, J. Kosmrlj, Curr. Org. Chem. 21, 1949 (2017)CrossRefGoogle Scholar
  73. 73.
    S. Chimichi, M. Boccalini, M.M. Hassan, G. Viola, F. Dall’Acqua, M. Curini, Tetrahedron 62, 90 (2006)CrossRefGoogle Scholar
  74. 74.
    S. Chimichi, M. Boccalini, A. Matteucci, Tetrahedron 63, 11656 (2007)CrossRefGoogle Scholar
  75. 75.
    C. Mitsos, J. Petrou, O. Igglessi-Markopoulou, J. Markopoulos, J. Heterocycl. Chem. 36, 881 (1999)CrossRefGoogle Scholar
  76. 76.
    G. Athanasellis, E. Gavrielatos, O. Igglessi-Markopoulou, J. Markopoulos, J. Heterocycl. Chem. 40, 645 (2003)CrossRefGoogle Scholar
  77. 77.
    A.V. Manaev, I.N. Okhrimenko, K.A. Lyssenko, Russ. Chem. Bull. 57, 1734 (2008)CrossRefGoogle Scholar
  78. 78.
    V.B. Kovalska, K.D. Volkova, A.V. Manaev, M.Y. Losytskyy, I.N. Okhrimenko, V.F. Traven, S.M. Yarmoluk, Dyes Pigm. 84, 159 (2010)CrossRefGoogle Scholar
  79. 79.
    A.B. Tathe, N. Sekar, J. Fluoresc. 26, 471 (2016)PubMedCrossRefGoogle Scholar
  80. 80.
    F.M.A.A. El-Taweel, S.Z.A. Sowellim, A.G.A. Elagamey, Bull. Chem. Soc. Jpn 68, 905 (1995)CrossRefGoogle Scholar
  81. 81.
    M.M. Girges, M.A. Hanna, H.M. Hassan, E.B. Moawad, Czech Chem. Commun. 53, 3179 (1988)CrossRefGoogle Scholar
  82. 82.
    F.M. El-Taweel, D.A. Ibrahim, M.A. Hanna, Boll. Chim. Farm. 140, 287 (2001)PubMedGoogle Scholar
  83. 83.
    G.V. Kalechits, V.K. Ol’khovik, I.I. Kalosha, E.D. Skakovskii, A.A. Pap, A.A. Zenyuk, Y.V. Matveenko, Russ. J. Gen. Chem. 71, 1257 (2001)CrossRefGoogle Scholar
  84. 84.
    S. Sarveswari, T.K. Raja, Indian J. Heterocycl. Chem. 16, 171 (2006)Google Scholar
  85. 85.
    R.S. Bhupathi, B.R. Devi, P.K. Dubey, Asian J. Chem. 23, 4215 (2011)Google Scholar
  86. 86.
    M. Roussaki, B. Hall, S.C. Lima, A.C. da Silva, S. Wilkinson, A. Detsi, Med. Chem. Lett. 23, 6436 (2013)CrossRefGoogle Scholar
  87. 87.
    M. Abass, M. Abdel-Megid, M. Hassan, Synth. Commun. 37, 329 (2007)CrossRefGoogle Scholar
  88. 88.
    M.M. Hassan, O. Farouk, J. Heterocycl. Chem. 54, 3133 (2017)CrossRefGoogle Scholar
  89. 89.
    S. Sarveswari, V. Vijayakumar, Arab. J. Chem. 9, S835 (2016)CrossRefGoogle Scholar
  90. 90.
    R.S. Bhupathi, B.R. Devi, P.K. Dubey, Indian J. Chem., Sect B 51, 855 (2012)Google Scholar
  91. 91.
    M. Abdel-Megid, M. Abass, M. Hassan, J. Heterocycl. Chem. 44, 315 (2007)CrossRefGoogle Scholar
  92. 92.
    F.M.A. El-Taweel, J. Heterocycl. Chem. 42, 943 (2005)CrossRefGoogle Scholar
  93. 93.
    T. Kappe, R. Aigner, M. Jöbstl, P. Hohengassner, W. Stadlbauer, Heterocycl. Commun. 1, 341 (1995)CrossRefGoogle Scholar
  94. 94.
    M.M. Hassan, S.M. Abdel-Kariem, T.E. Ali, Phosphorus Sulfur Silicon Rel. Elem. 192, 1290625 (2017)Google Scholar
  95. 95.
    B. Baruah, K. Dasu, B. Vaitilingam, A. Vanguri, S.R. Casturi, K.R. Yeleswarapu, Med. Chem. Lett. 14, 445 (2004)CrossRefGoogle Scholar
  96. 96.
    T. Arasakumar, S. Mathusalini, K. Lakshmi, P.S. Mohan, A. Ata, C.H. Lin, Synth. Commun. 46, 232 (2016)CrossRefGoogle Scholar
  97. 97.
    M. Sankaran, C. Kumarasamy, U. Chokkalingam, P.S. Mohan, Med. Chem. Lett. 20, 7147 (2010)CrossRefGoogle Scholar
  98. 98.
    S. Latypov, A. Balandina, M. Boccalini, A. Matteucci, K. Usachev, S. Chimichi, Eur. J. Org. Chem. 2008, 4640 (2008)CrossRefGoogle Scholar
  99. 99.
    J.H. Ye, K.Q. Ling, Y. Zhang, N. Li, J.H. Xu, J. Chem. Soc. Perkin Trans. 1, 2017 (1999)CrossRefGoogle Scholar
  100. 100.
    D.K. Kumar, R. Rajkumar, S.P. Rajendran, Chem. Heterocycl. Compd. 52, 322 (2016)CrossRefGoogle Scholar

Copyright information

© Springer Nature B.V. 2018

Authors and Affiliations

  • Moaz M. Abdou
    • 1
    • 2
    • 3
  • Zeynel Seferoğlu
    • 4
  • Mahmoud Fathy
    • 1
  • Takashiro Akitsu
    • 5
  • Mamoru Koketsu
    • 6
  • Ruba Kellow
    • 3
  • Eric Amigues
    • 3
  1. 1.Egyptian Petroleum Research InstituteNasr City, CairoEgypt
  2. 2.Department of ChemistryUniversity of LiverpoolLiverpoolUK
  3. 3.Department of ChemistryXi’an Jiaotong Liverpool UniversitySuzhouPeople’s Republic of China
  4. 4.Department of ChemistryGazi UniversityAnkaraTurkey
  5. 5.Department of Chemistry, Faculty of ScienceTokyo University of ScienceTokyoJapan
  6. 6.Department of Chemistry and Biomolecular Science, Faculty of EngineeringGifu UniversityGifuJapan

Personalised recommendations