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Crystal Structure of 2-(Hexyloxy)benzo[b]phenazine-6,11-dione

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Cyclization of 2-chloro-3-((4-(hexyloxy)phenyl)amino)naphthalene-1,4-dione obtained from the reaction of 2,3-dichloro-1,4-naphthoquinone with 4-(hexyloxy)aniline by sodium azide in N,N-dimethylformamide (DMF) at 90–95°C gives 2-(hexyloxy)benzo[b]phenazine-6,11-dione. This is a remarkable example of a general procedure to prepare functionalized benzo[b]phenazine-6,11-dione derivatives. The structure of the title compound was confirmed by single crystal X-ray diffraction analysis. The compound, C22H20N2O3, crystallizes in the sp. gr. P\(\bar {1}\), Z = 2. Both O atoms and one of N atoms are involved in hydrogen bonds forming a network. Besides, there is offset stacking interaction between the planes of polycyclic systems with interplanar distance of 3.383 Å.

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  1. E. M. Hodnett, C. Wongwiechintana, W. J. Dunn, and P. Marrs, J. Med. Chem. 26 (4), 570 (1983).

    Article  Google Scholar 

  2. M. Vos, G. Esposito, J. N. Edirisinghe, et al., Science 336 (6086), 1306 (2012).

    Article  ADS  Google Scholar 

  3. L. Liu, W. Li, K. Koike, et al., Chem. Pharm. Bull. 52 (5), 566 (2004).

    Article  Google Scholar 

  4. S. M. Plaza and D. W. Lamson, Altern. Med. Rev. 10 (1), 24 (2005).

    Google Scholar 

  5. B. Bin Hafeez, M. S. Jamal, J. W. Fischer, et al., Int. J. Cancer 131 (9), 2175 (2012).

    Article  Google Scholar 

  6. P. Dandawate, E. Khan, S. Padhye, et al., Bioorg. Med. Chem. Lett. 22 (9), 3104 (2012).

    Article  Google Scholar 

  7. N. G. Clark, Pestic. Sci. 15 (1), 25 (1984).

    Article  Google Scholar 

  8. N. G. Clark, Pestic. Sci. 16 (1), 23 (1985).

    Article  Google Scholar 

  9. N. G. Clark, Pestic. Sci. 15 (3), 235 (1984).

    Article  Google Scholar 

  10. R. X. Faria, F. H. Oliveira, J. P. Salles, et al., Eur. J. Med. Chem. 143, 1361 (2018).

  11. V. K. Tandon, H. K. Maurya, S. Kumar, et al., RSC Adv. 4 (24), 12441 (2014).

    Article  Google Scholar 

  12. V. K. Tandon, R. V. Singh, and D. B. Yadav, Bioorg. Med. Chem. Lett. 14 (11), 2901 (2004).

    Article  Google Scholar 

  13. V. K. Tandon, D. B. Yadav, R. V. Singh, et al., Bioorg. Med. Chem. Lett. 15 (14), 3463 (2005).

    Article  Google Scholar 

  14. M. Janeczko, O. M. Demchuk, D. Strzelecka, et al., Eur. J. Med. Chem. 124, 1019 (2016).

  15. C. K. Ryu, Y. H. Kim, H. A. Im, et al., Bioorg. Med. Chem. Lett. 22 (1), 500 (2012).

    Article  Google Scholar 

  16. R. Pingaew, V. Prachayasittikul, A. Worachartcheewan, et al., Eur. J. Med. Chem. 103 (446) (2015).

  17. V. K. Tandon, M. K. Verma, H. K. Maurya, and S. Kumar, Tetrahedron Lett. 55 (46), 6331 (2014).

    Article  Google Scholar 

  18. H. J. Lee, J. S. Kim, M. E. Suh, et al., Eur. J. Med. Chem. 42 (2), 168 (2007).

    Article  Google Scholar 

  19. J. S. Kim, H. K. Rhee, H. J. Park, et al., Bioorg. Med. Chem. 15 (1), 451 (2007).

    Article  Google Scholar 

  20. H. J. Lee, J. S. Kim, S. Y. Park, et al., Bioorg. Med. Chem. 12 (7), 1623 (2004).

    Article  Google Scholar 

  21. Y. S. Kim, S. Y. Park, H. J. Lee, et al., Bioorg. Med. Chem. 11 (8), 1709 (2003).

    Article  Google Scholar 

  22. A. F. Tuyun, N. Bayrak, H. Yildirim, et al., J. Chem. (2015).

  23. I. Sieveking, P. Thomas, J. C. Estevez, et al., Bioorg. Med. Chem. 22 (17), 4609 (2014).

    Article  Google Scholar 

  24. Bruker, APEX2, version 2014.1-1 (Bruker AXS Inc., Madison, WI, 2014).

  25. Bruker, SAINT, version 8.34A (Bruker AXS Inc., Madison, WI, 2013).

  26. Bruker, SADABS, version 2012/2 (Bruker AXS Inc., Madison, WI, 2012).

  27. Bruker, SHELXTL, version 6.14 (Bruker AXS Inc., Madison, WI, 2000)

  28. A. L. Spek, Acta Crystallogr. D 65, 148 (2009).

    Article  Google Scholar 

  29. C. F. Macrae, P. R. Edgington, P. McCabe, et al., J Appl. Crystallogr. 39, 453 (2006).

    Article  Google Scholar 

  30. M. O. Sousa, G. Q. Silveira, and J. A. Gomez, Acta Crystallogr. E. 69, Pt. 8, o1317 (2013).

    Article  Google Scholar 

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The authors thank the Research Fund of Istanbul University for financial support of this work.

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Correspondence to M. Yıldız or A. F. Tuyun.

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Yıldız, M., Bayrak, N., Yıldırım, H. et al. Crystal Structure of 2-(Hexyloxy)benzo[b]phenazine-6,11-dione. Crystallogr. Rep. 63, 925–929 (2018).

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