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Synthesis, Biological Activity and Photophysical Studies of Ellipticine and its Derivatives: State of the Art

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Chemistry of Heterocyclic Compounds Aims and scope

The present review aims at surveying literature on the synthesis, biological and photophysical activities, especially anticancer properties, of tetracyclic natural compound ellipticine (5,11-dimethyl-6H-pyrido[4,3-b]carbazole) since its first isolation and synthesis in 1959.

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References

  1. Gribble, G. W.; Saulnier, M. G. Heterocycles 1985, 23, 1277.

    Article  CAS  Google Scholar 

  2. Garbett, N. C.; Graves, D. E. Curr. Med. Chem.: Anti-Cancer Agents 2004, 4, 149.

    CAS  PubMed  Google Scholar 

  3. Larue, L.; Rivalle, C.; Muzard, G.; Paoletti, C.; Bisagni, E.; Paoletti, J. J. Med. Chem. 1988, 31, 1951.

    Google Scholar 

  4. Gribble, G. W. In Advances in Heterocyclic Natural Product Synthesis; Pearson, W. H., Ed.; JAI Press: London, 1990, Vol. 1, p. 43.

  5. Kouadio, K.; Chenieux, J. C.; Rideau, M.; Viel, C. J. Nat. Prod. 1984, 47, 872.

    Article  CAS  PubMed  Google Scholar 

  6. Goodwin, S.; Smith, A. F.; Horning, E. C. J. Am. Chem. Soc. 1959, 81, 1903.

    Google Scholar 

  7. Marsais, F.; Pineau, P.; Nivolliers, F.; Mallet, M.; Turck, A.; Godard, A.; Queguiner, G. J. Org. Chem. 1992, 57, 565.

    Article  CAS  Google Scholar 

  8. Ruckdeschel, J. C.; Modi, S. P.; El-Hamouly, W.; Portuese, E.; Archer, S. J. Med. Chem. 1992, 35, 4854.

    Article  CAS  PubMed  Google Scholar 

  9. Woodward, R. B.; Iacobucci, G. A.; Hochstein, I. A. J. Am. Chem. Soc. 1959, 81, 4434.

    Article  CAS  Google Scholar 

  10. Mitra, A. K. Reson. 2021, 26, 1125.

    Article  CAS  Google Scholar 

  11. Ibrahim-Ouali, M.; Dumur, F. ARKIVOC 2018, (i), 216.

    Article  CAS  Google Scholar 

  12. Miller, C. M.; McCarthy, F. O. RSC Adv. 2012, 2, 8883.

    Article  CAS  Google Scholar 

  13. Mitra, A. K. J. Iran. Chem. Soc. 2021. DOI: https://doi.org/10.1007/s13738-021-02444-0.

  14. Knölker, H. J.; Reddy, K. R. Chem. Rev. 2002, 102, 4303.

    Article  PubMed  CAS  Google Scholar 

  15. Knolker, H. J. Curr. Org. Synth. 2004, 1, 309.

    Article  Google Scholar 

  16. Yin, J.; Ma, Y.; Li, G.; Peng, M.; Lin, W. Coord. Chem. Rev. 2020, 412, 213257.

    Article  CAS  Google Scholar 

  17. Altaf, A. A.; Shahzad, A.; Gul, Z.; Rasool, N.; Badshah, A.; Lal, B.; Khan, E. J. Drug Des. Med. Chem. 2015, 1, 1.

    Google Scholar 

  18. Golunski, S. E.; Jackson, D. Appl. Catal. 1986, 23, 1.

    Article  CAS  Google Scholar 

  19. Abdel-Raheem, S. A. A.; El-Dean, A. M. K.; Abd ul-Malik, M. A.; Abd-Ella, A. A.; Al-Taifi, E. A.; Hassanien, R.; El-Sayed, M. E. A.; Mohamed, S. K.; Zawam, S. A.; Bakhite, E. A. Curr. Chem. Lett. 2021, 10, 337.

  20. Kohn, K. W.; Waring, M. J.; Glaubiger, D.; Friedman, C. A. Cancer Res. 1975, 35, 71.

    CAS  PubMed  Google Scholar 

  21. Canals, A.; Purciolas, M.; Aymamí, J.; Coll, M. Acta Crystallogr., Sect. D: Biol. Crystallogr. 2005, 61, 1009.

    Article  CAS  Google Scholar 

  22. Dodin, G.; Schwaller, M. A.; Aubard, J.; Paoletti, C. Eur. J. Biochem. 1988, 176, 371.

    Article  CAS  PubMed  Google Scholar 

  23. Schwaller, M. A.; Aubard, J.; Auclair, C.; Paoletti, C.; Dodin, G. Eur. J. Biochem. 1989, 181, 129.

    Article  CAS  PubMed  Google Scholar 

  24. Monnot, M.; Mauffret, O.; Simon, V.; Lescot, E.; Psaume, B.; Saucier, J. M.; Charra, M.; Belehradek, J.; Fermandjian, S. J. Biol. Chem. 1991, 266, 1820.

    Google Scholar 

  25. Pedersen, J. M.; Bowman, W. R.; Elsegood, M. R.; Fletcher, A. J.; Lovell, P. J. J. Org. Chem. 2005, 70, 10615.

    Article  CAS  PubMed  Google Scholar 

  26. McKee, M. L.; Zheng, L.; O'Sullivan, E. C.; Kehoe, R.; Doyle Prestwich, B. M.; Mackrill, J. J.; McCarthy, F. O. Pathogens, 2020, 9, 58.

    Article  CAS  Google Scholar 

  27. Dračínský, M.; Sejbal, J.; Rygerová, B.; Stiborová, M. Tetrahedron Lett. 2007, 48, 6893.

    Article  CAS  Google Scholar 

  28. Zee, S.-H.; Su, H.-P. J. Chin. Chem. Soc. 1987, 34, 135.

    Article  CAS  Google Scholar 

  29. Stillwell, R. N. Thesis; Harvard University, 1964.

    Google Scholar 

  30. Sainsbury, M. Synthesis 1977, 437.

  31. Archer, S.; Ross, B. S.; Pica-Mattoccia, L.; Cioli, D. J. Med. Chem. 1987, 30, 1204.

    Article  CAS  PubMed  Google Scholar 

  32. Miller, R. B.; Dugar, S. Tetrahedron Lett. 1989, 30, 297.

    Article  CAS  Google Scholar 

  33. Miyaura, N.; Yanagi, T.; Suzuki, A. Synth. Commun. 1981, 11, 513.

    Article  CAS  Google Scholar 

  34. Liu, C. Y.; Knochel, P. J. Org. Chem. 2007, 72, 7106.

    Article  CAS  PubMed  Google Scholar 

  35. Negishi, E.; Valente, L. F.; Kobayashi, M. J. Am. Chem. Soc. 1980, 102, 3298.

    Article  CAS  Google Scholar 

  36. Miller, R. B.; Stowell, J. G. J. Org. Chem. 1983, 48, 886.

    Article  CAS  Google Scholar 

  37. Miller, R. B.; Moock, T. Tetrahedron Lett. 1980, 21, 3319.

    Article  CAS  Google Scholar 

  38. Marsais, F.; Pineau, P.; Nivolliers, F.; Mallet, M.; Turck, A.; Godard, A.; Queguiner, G. J. Org. Chem. 1992, 57, 565.

    Article  CAS  Google Scholar 

  39. May, C.; Moody, C. J. J. Chem. Soc., Perkin Trans. 1 1988, 247.

  40. May, C.; Moody, C. J. J. Chem. Soc., Chem. Commun. 1984, 926.

  41. Cranwell, P. A.; Saxton, J. E. J. Chem. Soc. 1962, 3482.

  42. Fujiwara, A. N.; Acton, E. M.; Goodman, L. J. Heterocycl. Chem. 1968, 5, 853.

    Article  CAS  Google Scholar 

  43. Konakahara, T.; Kiran, Y. B.; Okuno, Y.; Ikeda, R.; Sakai, N. Tetrahedron Lett. 2010, 51, 2335.

    Article  CAS  Google Scholar 

  44. Bäckvall, J. E.; Plobeck, N. A. J. Org. Chem. 1990, 55, 4528.

    Article  Google Scholar 

  45. Gribble, G. W.; Keavy, D. J.; Davis, D. A.; Saulnier, M. G.; Pelcman, B.; Barden, T. C.; Sibi, M. P.; Olson, E. R.; BelBruno, J. J. J. Org. Chem. 1992, 57, 5878.

    Article  CAS  Google Scholar 

  46. Ramkumar, N.; Raghavendra, M. S.; Nagarajan, R. Synlett 2014, 25, 2791.

    Article  CAS  Google Scholar 

  47. Ho, T.-L.; Hsieh, S.-Y. Helv. Chim. Acta 2006, 89, 111.

    Article  CAS  Google Scholar 

  48. Miki, Y.; Tada, Y.; Yanase, N.; Hachiken, H.; Matsushita, K.-i. Tetrahedron Lett. 1996, 37, 7753.

  49. Miki, Y.; Hachiken, H.; Yanase, N. J. Chem. Soc., Perkin Trans. 1 2001, 2213.

  50. Vann, K. R.; Ergün, Y.; Zencir, S.; Oncuoglu, S.; Osheroff, N.; Topcu, Z. Bioorg. Med. Chem. Lett. 2016, 26, 1809.

    Google Scholar 

  51. Tewey, K. M.; Chen, G. L.; Nelson, E. M.; Liu, L. F. J. Biol. Chem. 1984, 259, 9182.

    Article  CAS  PubMed  Google Scholar 

  52. Ergün, Y.; Patir, S.; Okay, G. J. Heterocycl. Chem. 1998, 35, 1445.

    Article  Google Scholar 

  53. Praly-Deprez, I.; Rivalle, C.; Huel, C.; Belehradek, J.; Paoletti, C.; Bisagni, E. J. Chem. Soc., Perkin Trans. 1 1991, 3165.

  54. Ketcha, D. M.; Gribble, G. W. J. Org. Chem. 1985, 26, 5451.

    Article  Google Scholar 

  55. Bennasar, M. L.; Roca, T.; Ferrando, F. J. Org. Chem. 2005, 70, 9077.

    Article  CAS  PubMed  Google Scholar 

  56. Ramkumar, N.; Nagarajan, R. Tetrahedron Lett. 2014, 55, 1104.

    Article  CAS  Google Scholar 

  57. Ramkumar, N.; Nagarajan, R. J. Org. Chem. 2014, 79, 736.

    Article  CAS  PubMed  Google Scholar 

  58. Moody, D. L.; Dyba, M.; Kosakowska-Cholody, T.; Tarasova, N. I.; Michejda, C. J. Bioorg. Med. Chem. Lett. 2007, 17, 2380.

    Article  CAS  PubMed  Google Scholar 

  59. Palacios, F.; Alonso, C.; Aparicio, D.; Rubiales, G.; de Los Santos, J. M. Tetrahedron 2007, 63, 523.

    Article  CAS  Google Scholar 

  60. Zhang, Q.; Shi, C.; Zhang, H.-R.; Wang, K. K. J. Org. Chem. 2000, 65, 7977.

    Article  CAS  PubMed  Google Scholar 

  61. Chaitanya, T. K.; Nagarajan, R. Org. Biomol. Chem. 2011, 9(12), 4662.

    Article  CAS  PubMed  Google Scholar 

  62. Froelich-Ammon, S. J.; Patchan, M. W.; Osheroff, N.; Thompson, R. B. J. Biol. Chem. 1995, 270, 14998.

    Article  CAS  PubMed  Google Scholar 

  63. Kizek, R.; Adam, V.; Hrabeta, J.; Eckschlager, T.; Smutny, S.; Burda, J. V.; Frei, E.; Stiborova, M. Pharmacol. Ther. 2012, 133, 26.

    Article  CAS  PubMed  Google Scholar 

  64. Sorace, R. A.; Sheid, B. Chem.-Biol. Interact. 1978, 23, 379.

    Article  CAS  PubMed  Google Scholar 

  65. Kohn, K. W.; Waring, M. J.; Glaubiger, D.; Friedman, C. A. Cancer Res. 1975, 35, 71.

    CAS  PubMed  Google Scholar 

  66. Ferlin, M. G.; Marzano, C.; Gandin, V.; Dall'Acqua, S.; Dalla Via, L. ChemMedChem 2009, 4, 363.

    Article  CAS  PubMed  Google Scholar 

  67. Capranico, G.; Giaccone, G.; Zunino, F.; Garattini, S.; D'Incalci, M. Cancer Chemother. Biol. Response Modif. 1997, 17, 114.

    CAS  PubMed  Google Scholar 

  68. Auclair, C. Arch. Biochem. Biophys. 1987, 259, 1.

    Article  CAS  PubMed  Google Scholar 

  69. Le Pecq, J. B.; Nguyen-Dat-Xuong; Gosse, C.; Paoletti, C. Proc. Natl. Acad. Sci. 1974, 71, 5078.

  70. Ross, W. E.; Glaubiger, D. L.; Kohn, K. W. Biochim. Biophys. Acta, Nucleic Acids Protein Synth. 1978, 519, 23.

  71. Ross, W. E.; Smith, M. C. Biochem. Pharmacol. 1982, 31, 1931.

    Google Scholar 

  72. Ross, W. E.; Bradley, M. O. Biochim. Biophys. Acta, Nucleic Acids Protein Synth. 1981, 654, 129.

  73. Auclair, C.; Paoletti, C. J. Med. Chem. 1981, 24, 289.

    Article  CAS  PubMed  Google Scholar 

  74. Stiborová, M.; Poljaková, J.; Martínková, E.; Bořek- Dohalská, L.; Eckschlager, T.; Kizek, R.; Frei, E. Interdiscip. Toxicol. 2011, 4, 98.

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  75. Le Pecq, J. B.; Gosse, C.; Nguyen-Dat-Xuong; Cros, S.; Paoletti, C.; Raynal, B.; Morizet, J. Cancer Res. 1976, 36, 3067.

  76. Auclair, C.; Voisin, E.; Banoun, H.; Paoletti, C.; Bernadou, J.; Meunier, B. J. Med. Chem. 1984, 27, 1161.

    Article  CAS  PubMed  Google Scholar 

  77. Bhuyan, B. K.; Fraser, T. J.; Li, L. H. Cancer Res. 1972, 32, 2538.

    CAS  PubMed  Google Scholar 

  78. Kuo, P. L.; Hsu, Y. L.; Chang, C. H.; Lin, C. C. Cancer Lett. 2005, 223, 291.

    Article  CAS  Google Scholar 

  79. Innis, M. A.; Lee, I. P. In Abstracts of Papers. Society of Toxicology. Eleventh Annual Meeting, Williamsburg, Virginia March 5–9, 1972; Academic Press, 1972, p. 30. https://www.toxicology.org/pubs/docs/Tox/1972Tox.pdf. DOI: https://doi.org/10.1016/0041-008X(72)90178-0.

  80. Liu, J.; Xiao, Y.; Allen, C. J. Pharm. Sci. 2004, 93, 132.

    Article  CAS  PubMed  Google Scholar 

  81. Searle, F.; Gac-Breton, S.; Keane, R.; Dimitrijevic, S.; Brocchini, S.; Sausville, E. A.; Duncan, R. Bioconjugate Chem. 2001, 12, 711.

    Article  CAS  Google Scholar 

  82. Liggins, R. T.; Burt, H. M. Adv. Drug Delivery Rev. 2002, 54, 191.

    Article  CAS  Google Scholar 

  83. Perrouault, L.; Asseline, U.; Rivalle, C.; Thuong, N. T.; Bisagni, E.; Giovannangeli, C.; Doan, T. Le.; Helene, C. Nature 1990, 344, 358.

    Article  CAS  PubMed  Google Scholar 

  84. Thakur, R.; Das, A.; Chakraborty, A. Phys. Chem. Chem. Phys. 2012, 14, 15369.

    Article  CAS  PubMed  Google Scholar 

  85. Fung, S. Y.; Duhamel, J.; Chen, P. J. Phys. Chem. A 2006, 110, 11446.

    Article  CAS  PubMed  Google Scholar 

  86. Thakur, R.; Das, A.; Chakraborty, A. Chem. Phys. Lett. 2013, 563, 37.

    Article  CAS  Google Scholar 

  87. Mitra, A. K.; Ghosh, S.; Sau, A.; Saha, C.; Basu, S. J. Lumin. 2015, 167, 233.

    Article  CAS  Google Scholar 

  88. Mitra, A. K.; Ghosh, S.; Sarangi, M. K.; Chakraborty, S.; Saha, C.; Basu, S. J. Mol. Struct. 2014, 1074, 617.

    Article  CAS  Google Scholar 

  89. Mitra, A. K. Reson. 2019, 24, 623.

    Article  Google Scholar 

  90. Mitra, A. K.; Sau, A.; Bera, S. C.; Chakraborty, S.; Saha, C.; Basu, S. J. Fluoresc. 2015, 25, 1931.

    Google Scholar 

  91. Mitra, A. K.; Ghosh, S.; Chakraborty, S.; Basu, S.; Saha, C. J. Lumin. 2013, 143, 693.

    Article  CAS  Google Scholar 

  92. Ghosh, S.; Mitra, A. K.; Saha, C.; Basu, S. J. Fluoresc. 2013, 23, 1179.

    Article  CAS  PubMed  Google Scholar 

  93. Lakowicz, J. R. Principles of Fluorescence Spectroscopy; Springer: New York, 2013.

  94. Sbai, M.; Lyazidi, S. A.; Lerner, D. A.; Del Castillo, B.; Martin, M. A. J. Pharm. Biomed. Anal. 1996, 14, 959.

    Article  CAS  PubMed  Google Scholar 

  95. Sbai, M.; Lyazidi, S. A.; Lerner, D. A.; Del Castillo, B.; Martin, M. A. Anal. Chim. Acta 1995, 303, 47.

    Article  CAS  Google Scholar 

  96. Chahine, J. M. E. H.; Bertigny, J. P.; Schwaller, M. A. J. Chem. Soc., Perkin Trans. 2 1989, 629.

  97. Mataga, N.; Kaifu, Y.; Koizumi, M. Bull. Chem. Soc. Jpn. 1956, 29, 465.

    Article  CAS  Google Scholar 

  98. Miskolczy, Z.; Biczók, L.; Jablonkai, I. Chem. Phys. Lett. 2006, 427, 76.

    Article  CAS  Google Scholar 

  99. Banerjee, S.; Pabbathi, A.; Sekhar, M. C.; Samanta, A. J. Phys. Chem. A 2011, 115, 9217.

    Article  CAS  PubMed  Google Scholar 

  100. do Cabo, J. L.; Faria, H. B.; Portugal, S. G.; Silva, M. A.; Brinn, I. M. Photochem. Photobiol. 1999, 69, 664.

  101. Froelich-Ammon, S. J.; Patchan, M. W.; Osheroff, N.; Thompson, R. B. J. Biol. Chem. 1995, 270, 14998.

    Article  CAS  PubMed  Google Scholar 

  102. Sarangi, M. K.; Mitra, A. K.; Sengupta, C.; Ghosh, S.; Chakraborty, S.; Saha, C.; Basu, S. J. Phys. Chem. C 2013, 117, 2166.

    Article  CAS  Google Scholar 

  103. Ghosh, S.; Mitra, A. K.; Pal, U.; Basu, S.; Saha, C. J. Mol. Struct. 2017, 1130, 810.

    Article  CAS  Google Scholar 

  104. Mitra, A. K.; Sau, A.; Pal, U.; Saha, C.; Basu, S. J. Fluoresc. 2017, 27, 1547.

    Article  CAS  PubMed  Google Scholar 

  105. Mitra, A. K.; Ghosh, S.; Sarangi, M. K.; Sau, A.; Saha, C.; Basu, S. J. Photochem. Photobiol., A 2014, 296, 66.

    Article  CAS  Google Scholar 

  106. Thakur, R.; Das, A.; Chakraborty, A. J. Photochem. Photobiol., B 2014, 130, 122.

    Article  CAS  Google Scholar 

  107. Sabín, J.; Prieto, G.; Ruso, J. M.; Messina, P. V.; Salgado, F. J.; Nogueira, M.; Costas, M.; Sarmiento, F. J. Phys. Chem. B 2009, 113, 1655.

    Article  PubMed  CAS  Google Scholar 

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  1. Department of Chemistry, Government General Degree College, Singur, Hooghly, West Bengal, Pin: 712409, India

    Amrit Krishna Mitra

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2022, 58(4/5), 178–192

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Mitra, A.K. Synthesis, Biological Activity and Photophysical Studies of Ellipticine and its Derivatives: State of the Art. Chem Heterocycl Comp 58, 178–192 (2022). https://doi.org/10.1007/s10593-022-03070-1

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