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Synthesis and evaluation of 2,3-indolotriterpenoids as new α-glucosidase inhibitors

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Abstract

A series of ring-A fused heterocycles of lupane, oleanane, ursane and dammarane triterpenoids were synthesized and evaluated for their inhibitory activity against α-glucosidase. An influence of the different types of triterpenoids with indole and pyrazine cycles on the activity was revealed. Among them, 2,3-indolo-lup-20(29)-en-28-oic acid with an IC50 of 1.8 µM was the most active compound being 221-fold more active than the market drug acarbose. In the most cases, the replacement of the indole by the pyrazine fragment provided the decreasing of activity (except dammarane type pyrazine derivative).

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Acknowledgements

The analyses were performed on the equipment of the Center of joint usage “Khimiya” of Ufa Institute of Chemistry, Russian Academy of Sciences. The work was partially financially supported by the Russian Foundation for Basic Research (project no. 10-03-90303). EFK gratefully acknowledges the President of Russian Federation for a young scientist stipendium 2016-2018 (SP-1507.2016.4).

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Authors and Affiliations

  1. Ufa Institute of Chemistry, Russian Academy of Sciences, 71, pr. Oktyabrya, Ufa, 450054, Russian Federation

    Elmira F. Khusnutdinova, Irina E. Smirnova, Oxana B. Kazakova & Anastasiya V. Petrova

  2. Bashkir State University, 32, Validy Str., 450076, Ufa, Russian Federation

    Anastasiya V. Petrova

  3. Institute of Chemistry, Vietnamese Academy of Science and Technology, 18 Hoang Quoc Viet Str., Cau Giay Dist., Hanoi, Vietnam

    Nguyen Thi Thu Ha & Do Quoc Viet

Authors
  1. Elmira F. Khusnutdinova
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  2. Irina E. Smirnova
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  3. Oxana B. Kazakova
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  4. Anastasiya V. Petrova
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  5. Nguyen Thi Thu Ha
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  6. Do Quoc Viet
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Correspondence to Oxana B. Kazakova.

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Khusnutdinova, E.F., Smirnova, I.E., Kazakova, O.B. et al. Synthesis and evaluation of 2,3-indolotriterpenoids as new α-glucosidase inhibitors. Med Chem Res 26, 2737–2742 (2017). https://doi.org/10.1007/s00044-017-1972-0

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  • DOI: https://doi.org/10.1007/s00044-017-1972-0

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