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Dimerization of Pheophorbide а with Activated Carboxylic Group in the Reaction with Ethylenediamine

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Abstract

The interaction of ethylenediamine with pheophorbide a, carboxylic group of the latter being activated with di-tert-butyl dicarbonate, has been studied. Acylation of two amino groups of ethylenediamine with activated pheophorbide a and the formation of phorbine-phorbine dimer with the macrocycles bound in the dimer via amide bonding with ethylenediamine bridge have been demonstrated. It has also be found that the phorbine-phorbine dimer is formed even in large excess of ethylenediamine with respect to pheophorbide a.

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References

  1. Nyman, E.S. and Hynninen, P.H., J. Photochem. Photobiol. (B), 2004, vol. 73, no. 1–2, p. 1. doi 10.1016/j.jphotobiol.2003.10.002

    Article  CAS  Google Scholar 

  2. DeRosa, M.C. and Crutchley, R.J., Coord. Chem. Rev., 2002, vols. 233–234, p. 351. doi 10.1016/S0010-8545 (02)00034-6

    Article  Google Scholar 

  3. Sternberg, E.D. and Dolphin, D., Tetrahedron, 1998, vol. 54, no. 17, p. 4151. doi 10.1016/S0040-4020(98) 00015-5

    Article  CAS  Google Scholar 

  4. Pandey Ravindra, K., J. Porph. Phthal., 2000, vol. 4, p. 368. doi 10.1002/(SICI)1099-1409(200006/07)4:4<368::AID-JPP244>3.0.CO;2-6

    Article  Google Scholar 

  5. Zheng, G., Aoudia, M., Lee, D., Rodgers, M.A., Smith, K.M., Dougherty, T.J., and Pandey, R.K., J. Chem. Soc. Perkin Trans. 1, 2000, p. 3113. doi 10.1039/b003367g

    Google Scholar 

  6. Pandey, R.K., Smith, K.M., and Dougherty, T.J., J. Med. Chem., 1990, vol. 33, no. 7, p. 2032. doi 10.1021/jm00169a038

    Article  CAS  PubMed  Google Scholar 

  7. Pandey, R.K., Constantine, S., Tsuchida, T., Zheng, G., Medforth, C.J., Aoudia, M., Kozyrev, A.N., Rodgers, M.A.J., Kato, H., Smith, K.M., and Dougherty, T.J., J. Med. Chem., 1997, vol. 40, no. 17, p. 2770. doi 10.1021/JM9702894

    Article  CAS  PubMed  Google Scholar 

  8. Pavlov, V.Y. and Ponomarev, G.V., Chem. Heterocycl. Compd., 2004, vol. 40, no. 4, p. 393. doi 10.1023/B:COHC.0000033531.25694.2e

    Article  CAS  Google Scholar 

  9. Belykh, D.V., Kopylov, E.A., Gruzdev, I.V., and Kuchin, A.V., Russ. J. Org. Chem., 2010, vol. 46, no. 4, p. 577. doi 10.1134/S1070428010040238

    Article  CAS  Google Scholar 

  10. Belykh, D.V., Tarabukina, I.S., Gruzdev, I.V., Kodess, M.I., and Kutchin, A.V., J. Porph. Phthal., 2009, vol. 13, nos. 8–9, p. 949. doi 10.1142/S1088424609001133

    Article  CAS  Google Scholar 

  11. Belykh, D.V., Buravlev, E.V., Mal’shakova, M.V., Parshukova, N.N., Kopylov, E.A., Gruzdev, I.V., Kuchin, A.V., Chem. Nat. Compd., 2011, vol. 47, no. 1, p. 85. doi 10.1007/s10600-011-9836-1

    Article  CAS  Google Scholar 

  12. Belykh, D.V. and Nikiforov, A.V., Macroheterocycles, 2011, vol. 4, no. 1, p. 34. doi 10.6060/mhc2011.1.07

    Article  CAS  Google Scholar 

  13. Li Li, Bae Byoungchan, Tran Thanh Huyen, Yoon Kwon Hyeok, Na Kun, and Huh Kang Moo, Carbohydr. Polym., 2011, vol. 86, no. 2, p. 708. doi 10.1016/j.carbpol.2011.05.011

    Article  CAS  Google Scholar 

  14. Belykh, D.V. and Mal’shakova, M.V., Butlerovsk. Soobshch., 2014, vol. 39, no. 10, p.35.

    Google Scholar 

  15. Belykh, D.V., Mal’shakova, M.V., Yudina, Yu.A., Zavadskaya, K.A., Khudyaev, V.M., and Kuchin, A.V., Russ. Chem. Bull., 2011, vol. 60, no. 4, p. 719. doi 10.1007/s11172-011-0112-0

    Article  CAS  Google Scholar 

  16. Mal’shakova, M.V., Belykh, D.V., Hudyaev, V.M., and Kuchin, A.V., Doklady Chem., 2011, vol. 436, no. 2, p. 19. doi 10.1134/S0012500811020017

    Article  CAS  Google Scholar 

  17. Gurinovich, G.P., Zorinab, T.E., Melnov, S.B., Melnova, N.I., Gurinovich, I.F., Grubina, L.A., Sarzhevskaya, M.V., and Cherenkevich, S.N., J. Photochem. Photobiol. (B), 1992, vol. 13, no. 1, p. 51. doi 10.1016/1011-1344(92)80039-X

    Article  CAS  Google Scholar 

  18. Belykh, D.V., Mal’shakova, M.V., Korochkina, M.G., Kataev, V.E., and Kuchin, A.V., Chem. Nat. Compd., 2011, vol. 47, no. 4, p. 612. doi 10.1007/s10600-011-0008-0

    Article  CAS  Google Scholar 

  19. Weller, A. and Livingston, R., J. Am. Chem. Soc., 1954, vol. 76, p. 1575. doi 10.1021/ja01635a029

    Article  CAS  Google Scholar 

  20. Ma, L., Dolphyn, D., Tetrahedron, 1996, vol. 52, no. 3, p. 849. doi 10.1016/0040-4020(95)00944-2

    Article  CAS  Google Scholar 

  21. Belykh, D.V., Karmanova, L.P., Spirikhin, L.V., and Kuchin, A.V., Russ. J. Org. Chem., 2007, vol. 43, no. 1, p. 126. doi 10.1134/S1070428007010174

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Institute of Chemistry, Komi Scientific Center, Ural Branch, Russian Academy of Sciences, ul. Pervomaiskaya 48, Syktyvkar, 167982, Russia

    D. V. Belykh & M. V. Malshakova

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  1. D. V. Belykh
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  2. M. V. Malshakova
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Correspondence to D. V. Belykh.

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Original Russian Text © D.V. Belykh, M.V. Malshakova, 2018, published in Zhurnal Obshchei Khimii, 2018, Vol. 88, No. 6, pp. 952–957.

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Belykh, D.V., Malshakova, M.V. Dimerization of Pheophorbide а with Activated Carboxylic Group in the Reaction with Ethylenediamine. Russ J Gen Chem 88, 1133–1137 (2018). https://doi.org/10.1134/S1070363218060142

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  • DOI: https://doi.org/10.1134/S1070363218060142

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