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β-Carbolines: synthesis of harmane, harmine alkaloids and their structural analogs by thermolysis of 4-aryl-3-azidopyridines and investigation of their optical properties

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Chemistry of Heterocyclic Compounds Aims and scope

Interest in β-carbolines is caused by the biological activity of these compounds and the use of their fluorescent properties in the study of their interaction with DNA and other biological targets, as well as with drug delivery vehicles. A new general method for the synthesis of harmane, harmine, and their structural analogs by thermolysis of substituted 4-aryl-3-azidopyridines was developed, and their optical properties were studied.

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References

  1. (а) Nenaah, G. Fitoterapia2010, 81, 779. a Mahmoudian, M.; Jalilpour, H.; Salehian, P. Iran. J. Pharmacol. Ther.2002, 1, 1.

  2. (a) Cao, R.; Peng, W.; Wang, Z.; Xu, A. Curr. Med. Chem. 2007, 14, 479. (b) Rao, R. N.; Maiti, B.; Chanda, K. ACS Comb. Sci.2017, 19, 199. (c) Dai, J.; Dan, W.; Schneider, U.; Wang, J. Eur. J. Med. Chem.2018, 157, 622.

  3. (a) Cao, R.; Peng, W.; Chen, H.; Ma, Y.; Liu, X.; Hou, X.; Guan, H.; Xu, A. Biochem. Biophys. Res. Commun. 2005, 338, 1557. (b) Bain, J.; Plater, L.; Elliott, M.; Shpiro, N.; Hastie, C. J.; Mclauchlan, H.; Klevernic, I.; Arthur, J. S. C.; Alessi, D. R.; Cohen, P. Biochem. J.2007, 408, 297. (c) Li, S.-P. Wang, Y.-W.; Qi, S.-L.; Zhang, Y.-P.; Deng, G.; Ding, W.-Z.; Ma, C.; Lin, Q.-Y.; Guan, H.-D.; Liu, W.; Cheng, X.-M.; Wang, C.-H. Front. Pharmacol. 2018, 9, 346. (d) Hara, E. S.; Ono, M.; Kubota, S.; Sonoyama, W.; Oida, Y.; Hattori, T.; Nishida, T.; Furumatsu, T.; Ozaki, T.; Takigawa, M.; Kuboki, T. Biochimie2013, 95, 374. (e) Pagano, B.; Caterino, M.; Filosa, R.; Giancola, C. Molecules2017, 22, 1831.

  4. Khan, H.; Patel, S.; Kamal, M. A. Curr. Drug Metab.2017, 18, 853.

    Article  CAS  Google Scholar 

  5. (a) Quintana, V. M.; Piccini, L. E.; Zenere, J. D. P.; Damonte, E. B.; Ponce, M. A.; Castilla, V. Antiviral Res.2016, 134, 26. (b) Ishida, J.; Wang, H.-K.; Oyama, M.; Cosentino, M. L.; Hu, C.-Q.; Lee, K.-H. J. Nat. Prod. 2001, 64, 958.

  6. Kwon, M. S.; Gierschner, J.; Seo, J.; Park, S. Y. J. Mater. Chem. 2014, 2, 2552.

    CAS  Google Scholar 

  7. (a) Paul, B. K.; Guchhait, N. J. Phys. Chem. B2011, 115, 10322. (b) Paul, B. K.; Guchhait, N. J. Phys. Chem. B 2011, 115, 11938. (c) Guan, H.; Liu, X.; Peng, W.; Cao, R.; Ma, Y.; Chen, H.; Xu, A. Biochem. Biophys. Res. Commun.2006, 342, 894. (d) Garcia-Zubiri, I. X.; Burrows, H. D.; de Melo, J. S. S.; Pina, J.; Monteserin, M.; Tapia, M. J. Photochem. Photobiol. 2007, 83, 1455.

  8. (a) Love, B. E. Org. Prep. Proced. Int. 1996, 28, 1. (b) Galvis, C. E. P.; Kouznetsov, V. V. Synthesis2017, 4535.

  9. (a) Rao, A. V. R.; Chavan, S. P.; Sivadasan, L. Tetrahedron1986, 42, 5065. (b) Fujita, H.; Nishikawa, R.; Sasamoto, O.; Kitamura, M.; Kunishima, M. J. Org. Chem. 2019, 84, 8380.

  10. Wang, Z.-X.; Xiang, J.-C.; Cheng, Y.; Ma, J.-T.; Wu, Y.-D.; Wu, A.-X. J. Org. Chem. 2018, 83, 12247.

    Article  CAS  Google Scholar 

  11. (a) Chalotra, N.; Ahmed, A.; Rizvi, M. A.; Hussain, Z.; Ahmed, Q. N.; Shah, B. A. J. Org. Chem. 2018, 83, 14443. (b) Namjoshi, O. A.; Gryboski, A.; Fonseca, G. O.; Linn, M. L. V.; Wang, Z.-J. Deschamps, J. R.; Cook, J. M. J. Org. Chem. 2011, 76, 4721. (c) Yan, Q.; Gin, E.; Banwell, M. G.; Willis, A. C.; Carr, P. D. J. Org. Chem. 2017, 82, 4328. (d) Zhang, H.; Larock, R. C. J. Org. Chem.2002, 67, 9318. (e) Dassonneville, B.; Witulski, B.; Detert, H. Eur. J. Org. Chem. 2011, 2836. f Pumphrey, A. L.; Dong, H.; Driver, T. G. Angew. Chem., Int. Ed. 2012, 51, 5920.

  12. Gaich, T.; Baran, P. S. J. Org. Chem. 2010, 75, 4657.

    Article  CAS  Google Scholar 

  13. Kaczanowska, K.; Eickhoff, H.; Albert, K.; Wiesmuller, K.-H.; Schaffner, A.-P. J. Heterocycl. Chem. 2011, 48, 792.

    Article  CAS  Google Scholar 

  14. (a) Krinochkin, A. P.; Kopchuk, D. S.; Chepchugov, N. V.; Kim, G. A.; Kovalev, I. S.; Rahman, M.; Zyryanov, G. V.; Majee, A.; Rusinov, V. L.; Chupakhin, O. N. Chin. Chem. Lett.2017, 28, 1099. (b) Weller, D. D.; Luellen, G. R.; Weller, D. L. J. Org. Chem.1982, 47, 4803.

  15. Katritzky, A. R.; Denisenko, A.; Arend, M. J. Org. Chem. 1999, 64, 6076.

    Article  CAS  Google Scholar 

  16. Nesnow, S.; Miyazaki, T.; Khwaja, T.; Meyer, R. B.; Heidelberger, C. J. Med. Chem.1973, 16, 524.

    Article  CAS  Google Scholar 

  17. (a) Huang, X.; Keillor, J. W. Tetrahedron Lett.1997, 38, 313. b) Huang, X.; Seid, M.; Keillor, J. W. J. Org. Chem.1997, 62, 7495.

  18. (a) Perez, M. A. M.; Guzman, M. C. C.; Toledo, J. H.; Almeida, M. B. J. Chem. Soc., Perkin Trans. 21986, 1573. (b) Reyman, D.; Vinas, M. H.; Poyato, J. M. L.; Pardo, A. J. Phys. Chem. A1997, 101, 768. (c) Tarzi, O. I.; Erra-Balsells, R. J. Photochem. Photobiol. B2006, 82, 79. (d) Pardo, A.; Reyman, D.; Martin, E.; Poyato, J. M. L.; Camacho, J. J.; Hidalgo, J.; Sanchez, M. J. Lumin.1988, 42, 163.

  19. Wolfbeis, O. S.; Furlinger, E. Z. Phys. Chem.1982, 129, 171.

    CAS  Google Scholar 

  20. Vignoni, M.; Rasse-Suriani, F. A. O.; Butzbach, K.; Erra- Balsells, R.; Epe, B.; Cabrerizo, F. M. Org. Biomol. Chem.2013, 11, 5300.

    Article  CAS  Google Scholar 

  21. Kumar, A.; Singh, S.; Mudahar, G. S.; Thind, K. S. Radiat. Phys. Chem.2006, 75, 737.

    Article  CAS  Google Scholar 

  22. Williams, A. T. R.; Winfield, S. A.; Miller, J. N. Analyst1983, 108, 1067.

    Article  CAS  Google Scholar 

  23. Allen, M. W. Measurement of Fluorescence Quantum Yields; Thermo Fisher Scientific: Madison. Technical note: 52019.

  24. Brouwer, A. M. Pure Appl. Chem.2011, 83, 2213.

    Article  CAS  Google Scholar 

  25. (a) Demir, A. S.; Sesenoglu, O.; UIku, D.; Arici, C. Helv. Chim. Acta.2004, 87, 106. (b) Elias, G.; Rao, M. N. A. Eur. J. Med. Chem.1988, 23, 379. (c) Szmant, H. H.; Basso, A. J. J. Am. Chem. Soc.1952, 74, 4397. (d) Bai, X.-G.; Xu, C.-L.; Zhao, S.-S.; He, H.-W.;Wang, Y.-C.; Wang, J.-X. Molecules2014, 19, 17256. (e) Yang, J.-X.; Tao, X.-T.; Yuan, C. X.; Yan, Y. X.; Wang, L.; Liu, Z.; Ren, Y.; Jiang, M. H. J. Am. Chem. Soc.2005, 127, 3278. (f) Garg, S.; Raghav, N. RSC Adv.2015, 5, 72937.

  26. Stecher, E. D.; Ryder, H. F. J. Am. Chem. Soc.1952, 74, 4392.

    Article  CAS  Google Scholar 

  27. (a) Hassanien, A. Z. A.; Ghozlan, S. A. S.; Elnagdi, M. H. J. Heterocycl. Chem.2003, 40, 225. (b) Shibata, K.; Urano, K.; Matsui, M. Bull. Chem. Soc. Jpn.1988, 61, 2199. (c) Sizova, E. E.; Arshinov, E. E.; Kotsareva, Y. A.; Glizdinskaya, L. V.; Sagitullina, G. P. Chem. Heterocycl. Compd.2017, 53, 1026. [Khim. Geterotsikl. Soedin.2017, 53, 1026.]

  28. Dong, J.; Shi, X.-X.; Yan, J.-J.; Xing, J.; Zhang Q.; Xiao, S. Eur. J. Org. Chem.2010, 36, 6987.

    Article  Google Scholar 

  29. (a) Huang, Y.-Q.; Song, H.-J.; Liu, Y.-X.; Wang, Q.-M. Chem.–Eur. J.2018, 24, 2065. (b) Mukhamedova, S.; Maekh, C. Kh.; Yunusov, S. Yu. Chem. Nat. Compd.1983, 19, 376. [Khim. Prirod. Soedin.1983, 19, 394.]

  30. (a) Duval, E.; Cuny, G. D. Tetrahedron Lett.2004, 45, 5411. (b) Dorofeenko, G. N.; Dulenko, L. V. Chem. Heterocycl. Compd.1969, 5, 313. [Khim. Geterotsikl. Soedin.1969, 417.]

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Acknowledgment

This work was financially supported by the Russian Foundation for Basic Research and the Ministry of Education of the Omsk Region (grant 16-43-550144p_a) and the Ministry of Education and Science of the Russian Federation (project 4.1657.2017 / 4.6)

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Authors and Affiliations

  1. F. M. Dostoevsky Omsk State University, 55a Mira Ave, Omsk, 644077, Russia

    Vladislav Yu. Shuvalov, Valeriya А. Elisheva, Anastasiya S. Belousova, Evgenii V. Arshinov, Larisa V. Glyzdinskaya, Marina А. Vorontsova & Galina P. Sagitullina

  2. Omsk State Technical University, 11 Mira Ave, Omsk, 644050, Russia

    Vladislav Yu. Shuvalov, Sergei А. Chernenko & Aleksander S. Fisyuk

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  1. Vladislav Yu. Shuvalov
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  2. Valeriya А. Elisheva
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  3. Anastasiya S. Belousova
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  9. Galina P. Sagitullina
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Correspondence to Galina P. Sagitullina.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2020, 56(1), 73–83

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Shuvalov, V.Y., Elisheva, V.А., Belousova, A.S. et al. β-Carbolines: synthesis of harmane, harmine alkaloids and their structural analogs by thermolysis of 4-aryl-3-azidopyridines and investigation of their optical properties. Chem Heterocycl Comp 56, 73–83 (2020). https://doi.org/10.1007/s10593-020-02625-4

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