Synthesis of new 2-aminoimidazolones with antiproliferative activity via base promoted amino-β-lactam rearrangement (CROSBI ID 221772)
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Podaci o odgovornosti
Dražić, Tonko ; Vazdar, Katarina ; Vazdar, Mario ; Đaković, Marijana ; Mikecin, Ana-Matea ; Kralj, Marijeta ; Malnar, Martina ; Hećimović, Silva ; Habuš, Ivan
engleski
Synthesis of new 2-aminoimidazolones with antiproliferative activity via base promoted amino-β-lactam rearrangement
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.
β-lactam ; guanidine ; 2-aminoimidazolone ; rearrangement ; antiproliferative activity
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Podaci o izdanju
Povezanost rada
Kemija, Temeljne medicinske znanosti