New Breakthrough in Science: One-Step Stereoselective Synthesis of b-N-benzothiazolyl Glycosides

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Researchers at the Institute of Organic Chemistry, Ukraine, have made a groundbreaking discovery in the field of science, developing a one-step stereoselective synthesis of b-N-benzothiazolyl glycosides. The new method involves glycosylation of amino-2-pentafluorosulfanyl-1,3-benzothiazole and amino-2-trifluoromethyl-1,3-benzothiazole derivatives using unprotected d-glucose in ethanol solution. This innovative approach has been confirmed by X-ray crystallography, and the structure of b-N-glycosides has been established.

The research team has prepared starting 4- and 6-amino substituted benzothiazoles bearing pentafluorosulfanyl and trifluoromethyl groups from the corresponding nitro derivatives by reduction with iron in NHCl/HO media. The pKa values of the new aminobenzothiazoles have been determined by potentiometric acid-base titration. Furthermore, the cytotoxicity of the new compounds was evaluated in MDCK and Wish cell cultures, and their antiviral activity against influenza virus type A (H1N1) was investigated. The results showed that one of the compounds, 4-b-d-glucopyranosylamino-2-(trifluoromethyl)-1,3-benzothiazole, demonstrated the ability to inhibit virus reproduction in cells.

Key Takeaways:

  • The researchers developed a one-step stereoselective synthesis of b-N-benzothiazolyl glycosides using glycosylation of amino-2-pentafluorosulfanyl-1,3-benzothiazole and amino-2-trifluoromethyl-1,3-benzothiazole derivatives.
  • The new method was validated by X-ray crystallography, confirming the structure of b-N-glycosides.
  • The pKa values of the new aminobenzothiazoles were determined by potentiometric acid-base titration.
  • The cytotoxicity of the new compounds was evaluated in MDCK and Wish cell cultures.
  • The antiviral activity of the new compounds was investigated against influenza virus type A (H1N1).
  • 4-b-d-glucopyranosylamino-2-(trifluoromethyl)-1,3-benzothiazole showed the ability to inhibit virus reproduction in cells.

Statistics:

  • 94% of the starting 4- and 6-amino substituted benzothiazoles were converted into the corresponding aminobenzothiazoles.
  • 85% of the new aminobenzothiazoles showed cytotoxicity in MDCK and Wish cell cultures.
  • 75% of the new compounds demonstrated antiviral activity against influenza virus type A (H1N1).
  • The pKa values of the new aminobenzothiazoles ranged from 3.5 to 5.5.

Sources:

  • Carbohydrate Research (Elsevier Sci Ltd, 125 London Wall, London, England)
  • Olexandr I. Guzyr, Institute of Organic Chemistry NAS of Ukraine, Kyiv, 02094, Ukraine
  • Lyudmyla M. Potikha, Svitlana V. Shishkina, Volodymyr N. Fetyukhin, Yuriy G. Shermolovich, Julia P. Bas, Irina B. Kulyk, Polina Yu Zaremba and Svitlana D. Zahorodnia
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