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Cyclic Dithiophosphoric Acids in Reactions with (S)-(–)-Nicotine

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Abstract

Cyclic dithiophosphoric acids derived from (2S,3S)-(+)-dimetyl tartrate, 2,3-dihydroxynaphthalene, 2,2'-dihydroxybiphenyl, and racemic 1,1'-bi(2-naphthol) react with (S)-(–)-nicotine to form 5-(pyridine)-1-methylpyrrolydinium dithiophosphates which showed high antimicrobial activity against Bacillus cereus and Candida albicans.

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REFERENCES

  1. Modern Alkaloids: Structure, Isolation, Synthesis and Biology, Fattorusso, E. and Taglialatela-Scafati, O., Eds., Weinheim: Wiley-VCH, 2008.

  2. Analytical Determination of Nicotine and Related Compounds and their Metabolites, Gorrod, J.W., and Jacob, P., Eds., Amsterdam: Elsevier Science B.V., 1999.

  3. Cushnie, T.P.T., Cushnie, B., and Lamb, A.J., Int. J. Antimicrob. Agents, 2014, vol. 44, p. 377. https://doi.org/10.1016/j.ijantimicag.2014.06.001

    Article  CAS  PubMed  Google Scholar 

  4. Rice, L.B., Am. J. Med., 2006, vol. 119, Suppl. 1, p. S11. https://doi.org/10.1016/j.amjmed.2006.03.012

  5. Morjan, R.Y., Mkadmh, A.M., Beadham, I., Elmanama, A.A., Mattar, M.R., Raftery, J., Pritchard, R.G., Awadallah, A.M., and Gardiner, J.M., Bioorg. Med. Chem. Lett., 2014, vol. 24, p. 5796. https://doi.org/10.1016/j.bmcl.2014.10.029

    Article  CAS  PubMed  Google Scholar 

  6. Chohan, Z.H., Rau, A., Noreen, S., Scozzafava, A., and Supuran, C.T., J. Enzyme Inhib. Med. Chem., 2002, vol. 17, p. 101. https://doi.org/10.1080/14756360290024209

    Article  CAS  PubMed  Google Scholar 

  7. Judge, V., Narasimhan, B., Ahuja, M., Sriram, D., Yogeeswari, P., De Clercq, E., Pannecouque, C., and Balzarini, J., Med. Chem., 2012, vol. 9, p. 53. https://doi.org/10.1007/s00044-011-9662-9

    Article  CAS  Google Scholar 

  8. Wei, X., Sumithran, S.P., Deaciuc, A.G., Burton, H.R., Bush, L.P., Dwoskin, L.P., and Crooks, P.A., Life Sci., 2005, vol. 78, p. 495. https://doi.org/10.1016/j.lfs.2005.09.009

    Article  CAS  PubMed  Google Scholar 

  9. Wagner, F.F. and Comins, D.L., Tetrahedron, 2007, vol. 63, p. 8065. https://doi.org/10.1016/j.tet.2007.04.100

    Article  CAS  Google Scholar 

  10. Gandhi, P.T., Athmaram, T.N., and Arunkumar, G.R., Bioorg. Med. Chem., 2016, vol. 24, p. 1637. https://doi.org/10.1016/j.bmc.2016.02.035

    Article  CAS  PubMed  Google Scholar 

  11. Lin, N.-H., WO Patent no. WO 1994004152A1, 1992.

  12. Amy, C.M. and Kirshner, N., J. Neurochem., 1981, vol. 36, p. 847. https://doi.org/10.1111/j.1471-4159.1981.tb01671.x

    Article  CAS  PubMed  Google Scholar 

  13. Ofoegbu, O., Ike, D.C., Batiha, G.E.-S., Fouad, H., Srichana, R.S., and Nicholls, I., Polymers, 2021, vol. 13, p. 3363. https://doi.org/10.3390/polym13193363

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  14. Darvas, B., World Crop Pests, 1997, vol. 7, part B, p. 165. https://doi.org/10.1016/S1572-4379(97)80082-6

    Article  Google Scholar 

  15. Erickson, P.S., Murphy, M.R., and Clark, J.H., J. Dairy Sci., 1992, vol. 75, p. 1078. https://doi.org/10.3168/jds.S0022-0302(92)77852-7

    Article  CAS  PubMed  Google Scholar 

  16. Dang, T., Nizamov, I.S., Salikhov, R.Z., Sabirzyanova, L.R., Vorobev, V.V., Burganova, T.I., Shaidoullina, M.M., Batyeva, E.S., Cherkasov, R.A., and Abdullin, T.I., Bioorg. Med. Chem., 2019, vol. 25, p. 100. https://doi.org/10.1016/j.bmc.2018.11.017

    Article  CAS  Google Scholar 

  17. Nizamov, I.S., Timushev, I.D., Salikhov, R.Z., Nizamov, I.D., Nikitin, Ye.N., Shulaeva, M.P., Pozdeev, O.K., Voznesenskaya, T.Yu., Batyeva, E.S., and Cherkasov, R.A., Asian J. Chem., 2020, vol. 32, p. 329. https://doi.org/10.14233/ajchem.2020.22381

    Article  CAS  Google Scholar 

  18. Dictionary of Organophosphorus Compounds, Edmundson, R.S., Ed., London–N.Y.: Chapman and Hall Ltd., 1988.

  19. Chauhan, H.P.S., Bhasin, C.P., Srivastava, G., and Mehrotra, R.C., Phosphorus Sulfur, 1983, vol. 15, p. 99. https://doi.org/10.1080/03086648308073283

    Article  CAS  Google Scholar 

  20. Chen, W., Wang, M., and Ge, W., CN Patent no. CN 1154370, 1997; Chem. Abstr., 1999, vol. 131, p. 351459t.

    Google Scholar 

  21. Nitsure, A., Patel, D., and Wairkar, S., Pharm. Develop. Technol., 2020, vol. 25, p. 376. https://doi.org/10.1080/10837450.2019.1705487

    Article  CAS  Google Scholar 

  22. Crutchfield, M.M., Dungan, C.H., Letcher, J.H., Mark, V., and Van Wazer, J.R., Topics in Phosphorus Chemistry. P31 Nuclear Magnetic Resonance, Grayson, M. and Griffith, E.J., Eds., New York: Wiley and Sons, 1967, vol. 5.

  23. Shagidullin, R.R., Chernova, A.V., Vinogradova, V.S., and Mukhametov, F.S., Atlas IK-spektrov fosfororganicheskikh soyedineniy (Atlas of IR Spectra of Organophosphorus Compounds), Moscow: Nauka, 1984.

  24. Pozdeev, O.K., Meditsinskaya mikrobiologiya (Medical Microbiology), Moscow: GEOTAR-MED, 2001.

  25. Keil, B., Herout, V., Hudlicky, M., Ernest, I., Protiva, M., Komers, J.G.R., and Moravek, J., Laboratorni Technika Organicke Chemie, Keil, B., Ed., Praha: Nakladatelstvi Československe academie ved, 1963.

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ACKNOWLEDGMENTS

The authors are grateful to O.K. Pozdeev and M.P. Shulaeva (Kazan State Medical Academy) for antimicrobial studies.

The authors are grateful to the staff of the Distributed Collective Spectral Analytical Center for the Study of the Structure, Composition and Properties of Substances and Materials, Kazan Research Center, Russian Academy of Sciences, for spectral measurements and elemental analysis.

Funding

The work was supported by the Priority-2030 Strategic Academic Leadership Program, Kazan (Volga Region) Federal University.

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Authors and Affiliations

  1. Kazan (Volga region) Federal University, 420008, Kazan, Russia

    I. S. Nizamov, I. D. Timushev, I. D. Nizamov, E. S. Kobeleva & R. A. Cherkasov

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  1. I. S. Nizamov
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  2. I. D. Timushev
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  3. I. D. Nizamov
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  4. E. S. Kobeleva
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  5. R. A. Cherkasov
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Correspondence to I. S. Nizamov.

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Additional information

Translated from Zhurnal Organicheskoi Khimii, 2022, Vol. 58, No. 8, pp. 823–831 https://doi.org/10.31857/S0514749222080067.

In memory of Academician A.I. Konovalov

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Nizamov, I.S., Timushev, I.D., Nizamov, I.D. et al. Cyclic Dithiophosphoric Acids in Reactions with (S)-(–)-Nicotine. Russ J Org Chem 58, 1108–1114 (2022). https://doi.org/10.1134/S1070428022080061

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  • DOI: https://doi.org/10.1134/S1070428022080061

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