A straightforward synthesis of natural oxygenated ent-kaurenoic acid derivatives

Morărescu (Chetraru) Olga; Grinco Marina; Kulciţki Veaceslav; Barba Alic; Garbuz Olga; Gudumak V.; Gulya Aurelian; Ungur Nikon

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690

SM ISO690:2012

MORĂRESCU (CHETRARU), Olga, GRINCO, Marina, KULCIŢKI, Veaceslav, BARBA, Alic, GARBUZ, Olga, GUDUMAK, V., GULYA, Aurelian, UNGUR, Nikon. A straightforward synthesis of natural oxygenated ent-kaurenoic acid derivatives. In: Synthetic Communications, 2021, nr. 1(51), pp. 123-133. ISSN 0039-7911. DOI: https://doi.org/10.1080/00397911.2020.1821225

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Synthetic Communications

Numărul 1(51) / 2021 / ISSN 0039-7911 /ISSNe 1532-2432

A straightforward synthesis of natural oxygenated ent-kaurenoic acid derivatives

DOI:https://doi.org/10.1080/00397911.2020.1821225

Pag. 123-133

Morărescu (Chetraru) Olga¹, Grinco Marina¹, Kulciţki Veaceslav¹, Barba Alic¹, Garbuz Olga²³, Gudumak V.⁴, Gulya Aurelian², Ungur Nikon¹

¹ Institute of Chemistry,
² Moldova State University,
³ Institute of Zoology,
⁴ ”Nicolae Testemițanu” State University of Medicine and Pharmacy

Disponibil în IBN: 6 aprilie 2021

Rezumat

The paper presents the synthesis of some natural diterpenoids of ent-kauranic structure, starting from ent-kaur-16-en-19-oic acid, a natural diterpenoid readily available from the dried wastes of sunflower (Helianthus annuus L.). The reported ent-16α,17-dihydroxykauran-19-oic, ent-16α-hydroxy-17-acetoxykauran-19-oic and ent-16α,17-diacetoxykauran-19-oic acids have been previously isolated from different plant sources and showed diverse biological activities, including anti-HIV, anti-cancer and anti-Alzheimer properties. Their chemical synthesis has not been disclosed so far. Additional cytotoxicity studies of the obtained compounds revealed a remarkable cell proliferative effect of parent ent-kaur-16-en-19-oic acid and two of its synthetic derivatives, which is in line with recent pioneering studies in this area.

Cuvinte-cheie
Allylic isomerization, bioactivity, cell proliferation, dihydroxilation, ent-16, ent-16α-hydroxy-17-acetoxykauran-19-oic acid, ent-16α17-dihydroxylkauran-19-oic acid, ent-16α17-epoxykauran-19-oic acid, ent-17-hydroxykaur-15-en-19-oic acid, ent-17-oxo-16R-kauran-19-oic acident-kaur-16-en-19-oic acid, ent-kaurane, epoxidation, natural diterpenoids, α17-diacetoxykauran-19-oic acid

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