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Synthesis and Cytotoxicity of Lupaneand Oleanane-Type Triterpenoid Conjugates with 1,3,4-Oxadiazole

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Chemistry of Natural Compounds Aims and scope

Lupane- and oleanane-type triterpene acid derivatives reacted with nicotinic- and isonicotinic-acid hydrazides to synthesize C-17 and C-20 acylhydrazides, dehydration of which formed the corresponding 1,3,4-oxadiazole derivatives. Cytotoxicity studies of the obtained compounds showed that conjugates of oleanolic acid with acylhydrazide and 1,3,4-oxadiazole fragments (bound to a pyridin-4-yl or pyridin-3-yl substituent) on the triterpene C-17 atom were active. The most active compound 3-oxo-28-nor-17-{2′-[1′,3′,4′-oxadiazol-5′-(pyridin-4-yl)]yl}olean-12(13)-ene inhibited the growth of leukemia HL-60(TB), RPMI-8226, SR, colon (HCT-116), kidney (A498), and prostate cancer cells (PC-3).

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ACKNOWLEDGMENT

The work was performed on topic No. AAAA-A20-120012090023-8 of a State Task. We thank the NCI for determining the cytotoxicity of 6–17.

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Authors and Affiliations

  1. Ufa Institute of Chemistry, Ufa Federal Research Center, Russian Academy of Sciences, 71 Prosp. Oktyabrya, Ufa, 450054, Russia

    N. I. Medvedeva & O. B. Kazakova

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  1. N. I. Medvedeva
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  2. O. B. Kazakova
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Correspondence to N. I. Medvedeva.

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Translated from Khimiya Prirodnykh Soedinenii, No. 3, May–June, 2021, pp. 414–418.

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Medvedeva, N.I., Kazakova, O.B. Synthesis and Cytotoxicity of Lupaneand Oleanane-Type Triterpenoid Conjugates with 1,3,4-Oxadiazole. Chem Nat Compd 57, 485–490 (2021). https://doi.org/10.1007/s10600-021-03393-z

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