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Synthesis of New Steroid-beta-Lactam Hybrids via Palladium-Catalyzed Aminocarbonylation


Habuš, Ivan; Balogh, Janos; Skoda-Foldes, Rita; Vazdar, Katarina
Synthesis of New Steroid-beta-Lactam Hybrids via Palladium-Catalyzed Aminocarbonylation // CHEMMEDCHEM, Chemistry Enabling Drug Discovery ; EFMC/ISMC 2012 ; XXIInd International Symposium on Medicinal Chemistry ; Book of Abstracts / Ortuzar, Natalia ; Williams, D., Scott ; Neubacher, Saskia ; Abel, Lisa (ur.).
Berlin: 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim, 2012. str. 300-300 (poster, međunarodna recenzija, sažetak, znanstveni)


Naslov
Synthesis of New Steroid-beta-Lactam Hybrids via Palladium-Catalyzed Aminocarbonylation

Autori
Habuš, Ivan ; Balogh, Janos ; Skoda-Foldes, Rita ; Vazdar, Katarina

Vrsta, podvrsta i kategorija rada
Sažeci sa skupova, sažetak, znanstveni

Izvornik
CHEMMEDCHEM, Chemistry Enabling Drug Discovery ; EFMC/ISMC 2012 ; XXIInd International Symposium on Medicinal Chemistry ; Book of Abstracts / Ortuzar, Natalia ; Williams, D., Scott ; Neubacher, Saskia ; Abel, Lisa - Berlin : 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim, 2012, 300-300

Skup
XXIInd International Symposium on Medicinal Chemistry

Mjesto i datum
Berlin, Njemačka, 02-06. 09. 2012

Vrsta sudjelovanja
Poster

Vrsta recenzije
Međunarodna recenzija

Ključne riječi
Steroid-beta-Lactam Hybrids; Palladium-Catalyzed Aminocarbonylation

Sažetak
The synthesis of a great number of molecular hybrids or 'chimeras' derived from steroids and other biomolecules or drugs have been reported in the literature. Steroidal beta-lactams were isolated from the plants Pachysandra terminalis and Pachysandra procumbens. The latter group of compounds showed antiestrogen-binding site inhibitory activity. There are also some reports on some steroid-beta-lactam hybrids prepared synthetically, including cholestane, androstane, estrane and cholane conjugates. Although the biological activity of most of the compounds has not been revealed, a number of 1, 2, 3-triazol-linked beta-lactam-bile acid conjugates exhibited significant antifungal and moderate antibacterial effect. In the present work, the enantiomericaly pure trans-3-amino-beta-lactams were coupled to the steroidal core via an amide bond constructed by palladium-catalyzed carbonylation reaction in order to obtain steroid-beta-lactam hybrids. Amino-beta-lactam derivatives have been used for the first time as nucleopiles in the aminocarbonylation reactions.

Izvorni jezik
Engleski

Znanstvena područja
Kemija



POVEZANOST RADA


Projekt / tema
098-0982915-2948 - Amino-beta-laktami - intermedijari u sintezi biološki interesantnih spojeva (Vlasta Tomašić, )

Ustanove
Institut "Ruđer Bošković", Zagreb