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Novel 9a, 11-bridged azalides : One-pot synthesis of N'-substituted 2-imino-1, 3-oxazolidines condensed to an azalide aglycone


Marušić Ištuk, Zorica; Čikoš, Ana; Gembarovski, Dubravka; Lazarevski, Gorjana; Đilović, Ivica; Matković-Čalogović, Dubravka; Kragol, Goran
Novel 9a, 11-bridged azalides : One-pot synthesis of N'-substituted 2-imino-1, 3-oxazolidines condensed to an azalide aglycone // Bioorganic & medicinal chemistry, 19 (2011), 1; 556-566 doi:10.1016/j.bmc.2010.10.061 (međunarodna recenzija, članak, znanstveni)


Naslov
Novel 9a, 11-bridged azalides : One-pot synthesis of N'-substituted 2-imino-1, 3-oxazolidines condensed to an azalide aglycone

Autori
Marušić Ištuk, Zorica ; Čikoš, Ana ; Gembarovski, Dubravka ; Lazarevski, Gorjana ; Đilović, Ivica ; Matković-Čalogović, Dubravka ; Kragol, Goran

Izvornik
Bioorganic & medicinal chemistry (0968-0896) 19 (2011), 1; 556-566

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
Macrolide ; aAzalide ; 2-Imino-1 ; 3-oxazolidine ; Mukaiyama reagent

Sažetak
An efficient one-pot method for the synthesis of novel 9a, 11-bridged 15-membered 9a-aza-9-deoxo-9ahomoerythromycin A and its 6-O-methyl analogue has been developed. The novel bicyclic azalide scaffold is characterized by an N'-substituted-2-imino-1, 3-oxazolidine moiety bound to a acrolactone ring between positions 9a and 11. Removal of the cladinose sugar from the starting compounds allows easy preparation of a small series of such bicyclic 3-keto and 3, 6-hemiketal azalide derivatives. A mechanism for the formation of N'-substituted-2-imino-1, 3-oxazolidines is discussed. Antibacterial properties of the prepared compounds were evaluated.

Izvorni jezik
Engleski

Znanstvena područja
Kemija



POVEZANOST RADA


Projekt / tema
119-1193079-1084 - Strukturno istraživanje bioloških makromolekula metodom rentgenske difrakcije (Dubravka Matković-Čalogović, )

Ustanove
Prirodoslovno-matematički fakultet, Zagreb

Časopis indeksira:


  • Current Contents Connect (CCC)
  • Web of Science Core Collection (WoSCC)
    • Science Citation Index Expanded (SCI-EXP)
    • SCI-EXP, SSCI i/ili A&HCI
  • Scopus
  • MEDLINE


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