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Pregled bibliografske jedinice broj: 782356

Synthesis of new 2-aminoimidazolones with antiproliferative activity via base promoted amino-β-lactam rearrangement


Dražić, Tonko; Vazdar, Katarina; Vazdar, Mario; Đaković, Marijana; Mikecin, Ana-Matea; Kralj, Marijeta; Malnar, Martina; Hećimović, Silva; Habuš, Ivan
Synthesis of new 2-aminoimidazolones with antiproliferative activity via base promoted amino-β-lactam rearrangement // Tetrahedron, 71 (2015), 49; 9202-9215 doi:10.1016/j.tet.2015.10.048 (međunarodna recenzija, članak, znanstveni)


Naslov
Synthesis of new 2-aminoimidazolones with antiproliferative activity via base promoted amino-β-lactam rearrangement

Autori
Dražić, Tonko ; Vazdar, Katarina ; Vazdar, Mario ; Đaković, Marijana ; Mikecin, Ana-Matea ; Kralj, Marijeta ; Malnar, Martina ; Hećimović, Silva ; Habuš, Ivan

Izvornik
Tetrahedron (0040-4020) 71 (2015), 49; 9202-9215

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

Ključne riječi
β-lactam ; guanidine ; 2-aminoimidazolone ; rearrangement ; antiproliferative activity

Sažetak
A facile and efficient transformation of amino- β-lactam guanidines to 2-aminoimidazolones is described. The base-promoted transformation proceeds in two steps, with the rearrangement of four-membered β-lactam ring to five membered imidazolone and subsequent E1cB elimination and formation of double bond at the 4- position of imidazolone ring, which is supported with quantum chemical calculations. The benzoylaminoimidazolone and 2-aminoimidazolone products are obtained in high yields. The benzoylaminoimidazolone products show antiproliferative activity in HCT116 (colon carcinoma) and H460 (lung carcinoma) cell lines.

Izvorni jezik
Engleski

Znanstvena područja
Kemija, Temeljne medicinske znanosti



POVEZANOST RADA


Projekt / tema
098-0982522-2525 - Mehanizam djelovanja kolesterola u nastanku Alzheimerove bolesti (Silva Hećimović, )
098-0982915-2948 - Amino-beta-laktami - intermedijari u sintezi biološki interesantnih spojeva (Vlasta Tomašić, )
119-1193079-1332 - Kemija metalnih kompleksa u reakcijama od biološkog značaja i novim materijalima (Zora Popović, )

Ustanove
Institut "Ruđer Bošković", Zagreb,
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


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