Synthesis of Chiral Melatonin Salts of Dithiophosphoric Acids Using Monoterpenyl Alcohol

Ilyas S. Nizamov; Ramazan Z. Salikhov; Ilnar D. Nizamov; Yevgeniy N. Nikitin; Gulnur G. Sergeenko; Rustam R. Davletshin; Marina P. Shulaeva; Oscar K. Pozdeev; Elvira S. Batyeva; Rafael A. Cherkasov

doi:10.14233/ajchem.2020.22509

Issue

Vol. 32 No. 6 (2020): Vol 32 Issue 6

Issue Published : May 30, 2020

This work is licensed under a Creative Commons Attribution 4.0 International License.

Synthesis of Chiral Melatonin Salts of Dithiophosphoric Acids Using Monoterpenyl Alcohol

https://doi.org/10.14233/ajchem.2020.22509

Ilyas S. Nizamov

A.M. Butlerov Chemical Institute, Kazan Federal University, Kazan, Russia; Federal State Budgetary Institution of Science Federal Research Center, Kazan Scientific Center of Russian Academy of Sciences, Kazan, Russia

Ramazan Z. Salikhov

Federal State Budgetary Institution of Science Federal Research Center, Kazan Scientific Center of Russian Academy of Sciences, Kazan, Russia

Ilnar D. Nizamov

A.M. Butlerov Chemical Institute, Kazan Federal University, Kazan, Russia

Yevgeniy N. Nikitin

Federal State Budgetary Institution of Science Federal Research Center, Kazan Scientific Center of Russian Academy of Sciences, Kazan, Russia

Gulnur G. Sergeenko

Federal State Budgetary Institution of Science Federal Research Center, Kazan Scientific Center of Russian Academy of Sciences, Kazan, Russia

Rustam R. Davletshin

A.M. Butlerov Chemical Institute, Kazan Federal University, Kazan, Russia

Marina P. Shulaeva

Department of Microbiology, Kazan State Medical Academy, Kazan, Russia

Oscar K. Pozdeev

Department of Microbiology, Kazan State Medical Academy, Kazan, Russia

Elvira S. Batyeva

Federal State Budgetary Institution of Science Federal Research Center, Kazan Scientific Center of Russian Academy of Sciences, Kazan, Russia

Rafael A. Cherkasov

A.M. Butlerov Chemical Institute, Kazan Federal University, Kazan, Russia

Corresponding Author(s) : Ilyas S. Nizamov

isnizamov@mail.ru

Asian Journal of Chemistry, Vol. 32 No. 6 (2020): Vol 32 Issue 6
Article Published : May 30, 2020

Abstract

Dithiophosphoric acids in the terms of (S)-(–)-menthol, (1S)-endo-(–)-borneol,(1R)-endo-(+)-fenchyl alcohol and (1S,2S,3S,5R)-(+)-isopinocampheol react with melatonin to form chiral N-acetyl 5-methoxytryptammonium dithiophosphates. The interations proceed via increase in the coordination of indole nitrogen of melatonin. The antibacterial and antifungal activity of N-acetyl 5-methoxytryptammonium dithiophosphate containing (+)-fenchyl substituent was established.

Keywords

Melatonin Borneol Fenchyl alcohol Dithiophosphoric acids Antimicrobial activity

Nizamov, I. S., Salikhov, R. Z., Nizamov, I. D., Nikitin, Y. N., Sergeenko, G. G., Davletshin, R. R., … Cherkasov, R. A. (2020). Synthesis of Chiral Melatonin Salts of Dithiophosphoric Acids Using Monoterpenyl Alcohol. Asian Journal of Chemistry, 32(6), 1511–1514. https://doi.org/10.14233/ajchem.2020.22509

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References

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Slayt (1%) involves 2-phenoxyethanol 1%, N,N-bis(3-aminopropyl) dodecylamine 1.5%, alkyl dimethylbenzylammonium chloride and didecyldimethylammonium chloride 2%, propanol-2 1%, lipase, copolymer of N,N-1,6-hexanediylbis(N-cyanoguanidine) with 1,6- hexadiamine hydrochloride 1% and protease. http://dezr.ru/preparat/slayt (accessed July 27, 2019).

References

V. Srinivasan, M. Mohamed and H. Kato, Recent Pat. Endocr. Metab. Immune Drug Discov., 6, 30 (2012); https://doi.org/10.2174/187221412799015317

J.R. Vielma, E. Bonilla, L. Chacin-Bonilla, M. Mora, Sh. MedinaLeendertz and Ya. Bravo, Acta Trop., 137, 31 (2014); https://doi.org/10.1016/j.actatropica.2014.04.021

O.F. Tekbas, R. Ogur, A. Korkmaz, A. Kilic and R.J. Reiter, J. Pineal Res., 44, 222 (2008); https://doi.org/10.1111/j.1600-079X.2007.00516.x

N. Ma, X. Ma, J. Zhang, R.J. Reiter and X. Ma, Med. Res. Rev., 40, 606 (2020); https://doi.org/10.1002/med.21628

F. Shaki, S. Ashari and N. Ahangar, Biomed. Pharmacother., 84, 1172 (2016); https://doi.org/10.1016/j.biopha.2016.10.053

G. Endrici, Melatonin and an Antimicrobial or Antibacterial Agent for the Treatment of Acne, U.S. Patent 20140199413 (2014).

D.E.C. Corbridge, Phosphorus: Chemistry, Biochemistry and Technology, CRC Press: London, edn 6 (2013).

I.S. Nizamov, A.V. Sofronov, L.A. Al’metkina, R.Z. Musin and R.A. Cherkasov, Russ. J. Gen. Chem., 80, 1722 (2010); https://doi.org/10.1134/S1070363210080268

I.S. Nizamov, G.T. Gabdullina, L.A. Al’metkina, R.R. Shamilov, E.S. Batyeva and R.A. Cherkasov, Russ. J. Gen. Chem., 82, 1751 (2012); https://doi.org/10.1134/S1070363212100209

I.S. Nizamov, G.T. Gabdullina, D.A. Terenzhev, A.R. Nurmukhametov, I.D. Nizamov and R.A. Cherkasov, Phosphorus Sulfur Silicon Rel. Elem., 189, 1354 (2014); https://doi.org/10.1080/10426507.2013.860531

I.S. Nizamov, L.A. Al’metkina, G.T. Gabdullina, R.R. Shamilov, A.V. Sofronov, L.E. Nikitina, S.A. Lisovskaya, N.I. Glushko and R.A. Cherkasov, Russ. Chem. Bull., 61, 2370 (2012); https://doi.org/10.1007/s11172-012-0336-7

Sigma-Aldrich, p. 1157 (2003-2004).

M.M. Crutchfield, C.H. Dungan, J.H. Letcher, V. Mark and J.R. Van Wazer, eds. M. Grayson and E.J. Griffith, P31 Nuclear Magnetic Resonance, John Wiley & Sons: New York, vol. 5, p. 492 (1967).

N.B. Colthup, L.H. Daly and S.E. Wiberley, Introduction to Infrared and Raman Spectroscopy, Academic Press: New York (1964).

R.K. Manoharan, J.-H. Lee and J. Lee, Front. Microbiol., 8, 1476 (2017); https://doi.org/10.3389/fmicb.2017.01476

Slayt (1%) involves 2-phenoxyethanol 1%, N,N-bis(3-aminopropyl) dodecylamine 1.5%, alkyl dimethylbenzylammonium chloride and didecyldimethylammonium chloride 2%, propanol-2 1%, lipase, copolymer of N,N-1,6-hexanediylbis(N-cyanoguanidine) with 1,6- hexadiamine hydrochloride 1% and protease. http://dezr.ru/preparat/slayt (accessed July 27, 2019).

Issue

Vol. 32 No. 6 (2020): Vol 32 Issue 6

Synthesis of Chiral Melatonin Salts of Dithiophosphoric Acids Using Monoterpenyl Alcohol

Corresponding Author(s) : Ilyas S. Nizamov

Abstract

Keywords

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