Synthesis of new epi-manoyloxide derivatives with azide and gamma-lactam functional groups
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2023-05-19 11:39
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547.596:547.23 (1)
Chimie organică (475)
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VASILIEV, Alexei, GÎRBU, Vladilena, MORĂRESCU (CHETRARU), Olga, KULCIŢKI, Veaceslav. Synthesis of new epi-manoyloxide derivatives with azide and gamma-lactam functional groups. In: Life sciences in the dialogue of generations: connections between universities, academia and business community, Ed. 2, 29-30 septembrie 2022, Chişinău. Chișinău, Republica Moldova: Moldova State University, 2022, p. 228. ISBN 978-9975-159-80-7.
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Life sciences in the dialogue of generations: connections between universities, academia and business community 2022
Conferința "Life sciences in the dialogue of generations: connections between universities, academia and business community"
2, Chişinău, Moldova, 29-30 septembrie 2022

Synthesis of new epi-manoyloxide derivatives with azide and gamma-lactam functional groups

CZU: 547.596:547.23

Pag. 228-228

Vasiliev Alexei, Gîrbu Vladilena, Morărescu (Chetraru) Olga, Kulciţki Veaceslav
 
Institute of Chemistry
 
Disponibil în IBN: 25 noiembrie 2022


Rezumat

Manoyloxides have the carbon skeleton of the natural diterpenoid forskolin, which is a relevant secondary metabolite isolated from Coleus forskohlii with a myriad of therapeutic activities based on its ability to penetrate the cell membranes and stimulate the enzyme adenylyl cyclase. Other natural products belonging to the ent-series like ribenol and varodiol share the same tricyclic structure of manoyloxides and both have been reported in structure-activity relationship studies, providing derivatives with antimicrobial properties. These facts prompts following synthetic studies aimed to the generation of other manoyloxides derivatives with more and diverse functional groups. We report in the current communication the free radical carboazidation of epimeric manoyloxide leading to azide-functionalized epimanoyloxide and converted successfully to a related gamma-lactame. The lactamization step occurred spontaneously on catalytic hydrogenation of carboazidation product. The structure of the title product was demonstrated by spectroscopic means and showed a flexible nitrogen-centered chirality, which is characteristic for such hybrid heterocycles. The gamma-lactame is regarded as a surrogate of GABA derivatives and proved to be an efficient pharmacophore in our recent studies. Following investigations are in progress in order

Cuvinte-cheie
antimicrobial properties, gamma-lactame Coleus forskohlii, manoyloxides, spectroscopic methods,