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Development of approaches to fibrostatin F, N-acetyl-L-cysteinyl-containing 1,4-naphthoquinone metabolite of Streptomyces catenulae

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Abstract

A possibility of the synthesis of microbial metabolite Streptomyces catenulae fibrostatin F through the AcOH-catalyzed condensation of 5-hydroxy-3-hydroxymethyl-2,7-dimethoxy1,4-naphthoquinone and its related 3-chloromethyl, 3-acetoxymethyl, and 3-methoxymethyl derivatives with N-acetyl-L-cysteine and paraformaldehyde in 1,4-dioxane was studied. In these conditions, all naphthoquinones gave N-acetyl-S-[(8-hydroxy-3,6-dimethoxy-1,4-dioxonaphthalen-2-yl)methyl]-L-cysteine isomeric to the natural fibrostatin C.

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References

  1. R. H. Thomson, Naturally Occurring Quinones, 2nd ed., Academic Press, London—New York, 1971; 3rd ed., Chapman & Hall, London—New York, 1987; 4th ed., Blackie Academic and Professional, London—New York, 1997.

    Google Scholar 

  2. G. Bringmann, S. Rudenauer, A. Irmer, A. Bruhn, R. Brun, T. Heimberger, T. Stuhmer, R. Bargou, M. Chatterjee, Phytochem., 2008, 69, 2501

    Article  CAS  Google Scholar 

  3. F. Epifano, S. Genovese, S. Fiorito, V. Mathieu, R. Kiss, Phytochem. Rev., 2014, 13, 37.

    Article  Google Scholar 

  4. D. Brewer, W. C. Jen, G. A. Jones, A. Taylor, Can. J. Microbiol., 1984, 30, 1068.

    Article  CAS  Google Scholar 

  5. A. L. Baggish, D. R. Hill, Antimicrob, Agents Chemother., 2002, 46, 1163.

    Article  CAS  Google Scholar 

  6. D. Belorgey, D. A. Lanfranchi, E. Davioud-Charvet, Curr. Pharm. Design., 2013, 19, 14, 2512

    Article  Google Scholar 

  7. D. C. Schuck, S. B. Ferreira, L. N. Cruz, D. R. da Rocha, M. S. Moraes, M. Nakabashi, P. J. Rosenthal, V. F. Ferreira, C. R. S. Garcia, Malaria J., 2013, 12, 234

    Article  CAS  Google Scholar 

  8. A. Sharma, I. O. Santos, P. Gaur, V. F. Ferreira, C. R. S. Garcia, D. R. da Rocha, Eur. J. Med. Chem., 2013, 59, 48.

    Article  CAS  Google Scholar 

  9. Vitamin K Substances in Some Antiviral and Antineoplastic Drugs and Other Pharmaceutical Agents, IARC Monographs on the Evaluation of Carcinogenic Risks to Human, WHO, Lyon, 2000, V. 76, 417.

  10. N. P. Mishchenko, S. A. Fedoreev, V. L. Bagirova, Pharm. Chem. J. (Engl. Transl.), 2003, 37, 48 [Khim. Farm. Zh., 2003, 37, 49].

    Article  CAS  Google Scholar 

  11. P. B. Shreshta-Dawadi, S. Bittner, M. Fridkin, S. Rahimipour, Synthesis, 1996, 12, 1468

    Article  Google Scholar 

  12. S. Gorohovsky, S. Bittner, Amino Acids, 2001, 20, 135

    Article  CAS  Google Scholar 

  13. M. Alnabari, S. Bittner, Amino Acids, 2001, 20, 381

    Article  CAS  Google Scholar 

  14. C. Pachatouridis, Z. Iakovidou, E. Myoglou, D. Mourelatos, A. A. Pantazaki, V. P. Papageorgiou, A. Kotsis, M. Liakopoulou-Kyriakides, Anti-Cancer Drug., 2002, 13, 367

    Article  CAS  Google Scholar 

  15. A. R. Katritzky, L. Huang, R. Sakhuja, Synthesis, 2010, 42, 2011.

    Article  Google Scholar 

  16. V. Ph. Anufriev, V. L. Novikov, O. B. Maximov, G. B. Elyakov, D. O. Levitsky, A. V. Lebedev, S. M. Sadretdinov, A. V. Shvilkin, N. I. Afonskaya, M. Ya. Ruda, N. M. Cherpachenko, Bioorg. Med. Chem. Lett., 1998, 8, 587.

    Article  CAS  Google Scholar 

  17. S. Miyata, N. Ohhata, H. Murai, Y. Masui, M. Ezaki, S. Takase, M. Nishikawa, S. Kiyoto, M. Kohsaka, J. Antibiot., 1992, 45, 1029

    Article  CAS  Google Scholar 

  18. T. Aoyama, W. Zhao, F. Kojima, Y. Muraoka, H. Naganawa, T. Takeuchi, T. Aoyagi, J. Antibiot., 1993, 46, 1471

    Article  CAS  Google Scholar 

  19. J. R. Carney, S.-T. Hong, S. J. Gould, Tetrahedron Lett., 1997, 38, 3139

    Article  CAS  Google Scholar 

  20. P. Kulanthaivel, T. Perun, M. Belvo, R. Strobel, D. Poul, D. Williams, J. Antibiot., 1999, 52, 256

    Article  CAS  Google Scholar 

  21. X. Wang, K. A. Shaaban, S. I. Elshahawi, L. V. Ponomareva, M. Sunkara, Y. Zhang, G. C. Copley, J. C. Hower, A. J. Morris, M. K. Kharel, J. S. Thorson, J. Nat. Prod., 2013, 76, 1441.

    Article  CAS  Google Scholar 

  22. T. Ishimaru, T. Kanamaru, K. Ohta, H. Okazaki, J. Antibiot., 1987, 40, 1239.

    Article  Google Scholar 

  23. T. Ishimaru, T. Kanamaru, K. Ohta, H. Okazaki, J. Antibiot., 1987, 40, 1231

    Article  CAS  Google Scholar 

  24. T. Ishimaru, T. Kanamaru, T. Takahashi, H. Okazaki, J. Antibiot., 1988, 41, 1668.

    Article  CAS  Google Scholar 

  25. Sh. Saika, A. Ooshima, O. Yamanaka, Y. Okada, S.-I. Tanaka, Y. Ohnishi, Glaucoma, 1996, 234, 214.

    Google Scholar 

  26. E. Sabutskii, S. G. Polonik, V. A. Denisenko, P. S. Dmitrenok, Synthesis, 2014, 46, 2763.

    Article  CAS  Google Scholar 

  27. W. Buratti, G. P. Gardini, F. Minisci, F. Bertini, R. Galli, M. Perchinunno, Tetrahedron, 1971, 27, 3655

    Article  CAS  Google Scholar 

  28. D. I. Davies, M. J. Parrott, Free radical in organic synthesis, Springer-Verlag, Berlin—Heidelberg—New York, 1978, 76.

    Book  Google Scholar 

  29. S. E. Rakita, Quinone Methides, John Wiley & Sons, New Jersey, 2009, 1.

    Book  Google Scholar 

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Authors and Affiliations

  1. G. B. Elyakov Pacific Institute of Bioorganic Chemistry, Far-Eastern Branch of the Russian Academy of Sciences, 159 prosp. 100 let Vladivostoku, 690022, Vladivostok, Russian Federation

    Yu. E. Sabutskii, V. A. Denisenko, P. S. Dmitrenok & S. G. Polonik

Authors
  1. Yu. E. Sabutskii
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  2. V. A. Denisenko
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  3. P. S. Dmitrenok
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  4. S. G. Polonik
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Correspondence to S. G. Polonik.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 0774—0778, March, 2016.

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Sabutskii, Y.E., Denisenko, V.A., Dmitrenok, P.S. et al. Development of approaches to fibrostatin F, N-acetyl-L-cysteinyl-containing 1,4-naphthoquinone metabolite of Streptomyces catenulae . Russ Chem Bull 65, 774–778 (2016). https://doi.org/10.1007/s11172-016-1372-5

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  • DOI: https://doi.org/10.1007/s11172-016-1372-5

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