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Peer-reviewedCC BY-NC 4.0Organic & Biomolecular Chemistry

Synthesis of uniflorol B, a chromanone metabolite of Calea uniflora, and investigation of novel analogues as anti-leishmanial agents

Abstract

In this work, we report the first synthesis of the anti-leishmanial natural product uniflorol B. Uniflorol B is a chromanone metabolite first isolated from the Brazilian medicinal plant Calea uniflora Less. and possesses anti-leishmanial activity. We prepared uniflorol B, the E isomer of the natural product, through an 8-step approach featuring Kabbe condensation, regioselective ketone reduction and Morita-Baylis-Hillman elaboration of the side chain. We extended the methodology to four novel analogues and tested all compounds for their activity against various species of Leishmania. The most potent activity was seen with compound 22, with an IC50 of 64.8 µM against L. braziliensis.

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BibTeX
@article{niero2026synthesis,
  title = {{Synthesis of uniflorol B, a chromanone metabolite of Calea uniflora, and investigation of novel analogues as anti-leishmanial agents}},
  author = {Luana Budny Niero and Daniela Pagliara Lage and Eduardo Antonio Ferraz Coelho and Ricardo Andrez Machado-De-Ávila and James W. Barlow and Patrícia de Aguiar Amaral and Nicolas Gouault},
  journal = {Organic \& Biomolecular Chemistry},
  year = {2026},
  month = jun,
  doi = {10.1039/d6ob00708b},
  url = {https://hal.science/hal-05676022v1},
  note = {CC BY-NC 4.0},
}
RIS
TY  - JOUR
TI  - Synthesis of uniflorol B, a chromanone metabolite of Calea uniflora, and investigation of novel analogues as anti-leishmanial agents
AU  - Luana Budny Niero
AU  - Daniela Pagliara Lage
AU  - Eduardo Antonio Ferraz Coelho
AU  - Ricardo Andrez Machado-De-Ávila
AU  - James W. Barlow
AU  - Patrícia de Aguiar Amaral
AU  - Nicolas Gouault
PY  - 2026
DA  - 2026/06/24
JO  - Organic & Biomolecular Chemistry
DO  - 10.1039/d6ob00708b
UR  - https://hal.science/hal-05676022v1
AB  - In this work, we report the first synthesis of the anti-leishmanial natural product uniflorol B. Uniflorol B is a chromanone metabolite first isolated from the Brazilian medicinal plant Calea uniflora Less. and possesses anti-leishmanial activity. We prepared uniflorol B, the E isomer of the natural product, through an 8-step approach featuring Kabbe condensation, regioselective ketone reduction and Morita-Baylis-Hillman elaboration of the side chain. We extended the methodology to four novel analogues and tested all compounds for their activity against various species of Leishmania. The most potent activity was seen with compound 22, with an IC50 of 64.8 µM against L. braziliensis.
SN  - 1477-0520
SN  - 1477-0539
ER  -