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<p>Using modified derivatives of lupane triterpenoids, betulin and betulonic aldehyde, as an example, a convenient method was developed for obtaining (lupen-30-yl)triphenylphosphonium iodides containing no protective functional groups at positions 3 and 28 of the triterpene skeleton. The method consisted in the reaction of betulin and betulonic aldehyde iodo derivatives with triphenylphosphine in acetonitrile upon heating, which was accompanied by the formation of quaternary phosphonium salts with an allyl fragment at the phosphorus atom in quantitative yield. Reprecipitation of the obtained (lupen-30-yl)triphenylphosphonium salts from ethyl acetate led to their isomerization into (lupen-29-yl)-triphenylphosphonium salts. The (lupen-30-yl)triphenylphosphonium salts exhibited higher cytotoxic activity against human tumor cells MCF-7, MCF-7/Vinb, and PC-3 with IC<sub>50</sub> of 0.05–1.33 µmol L<sup>−1</sup> than the unmodified compounds.</p>

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Design, synthesis, and antitumor activity of triphenylphosphonium iodides containing C(30)-modified lupane triterpenoid moieties

  • 期刊论文

  • 发表日期：

    2025年5月1日

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  • O. V. Tsepaeva,
  • A. V. Nemtarev,
  • L. R. Idrisova,
  • B. I. Khairutdinov,
  • T. I. Abdullin,
  • E. V. Kuznetsova,
  • V. F. Mironov

摘要

Using modified derivatives of lupane triterpenoids, betulin and betulonic aldehyde, as an example, a convenient method was developed for obtaining (lupen-30-yl)triphenylphosphonium iodides containing no protective functional groups at positions 3 and 28 of the triterpene skeleton. The method consisted in the reaction of betulin and betulonic aldehyde iodo derivatives with triphenylphosphine in acetonitrile upon heating, which was accompanied by the formation of quaternary phosphonium salts with an allyl fragment at the phosphorus atom in quantitative yield. Reprecipitation of the obtained (lupen-30-yl)triphenylphosphonium salts from ethyl acetate led to their isomerization into (lupen-29-yl)-triphenylphosphonium salts. The (lupen-30-yl)triphenylphosphonium salts exhibited higher cytotoxic activity against human tumor cells MCF-7, MCF-7/Vinb, and PC-3 with IC50 of 0.05–1.33 µmol L−1 than the unmodified compounds.