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 b...

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Bibliographic Details
Published in:Tetrahedron 2015-12, Vol.71 (49), p.9202-9215
Main Authors: Dražić, Tonko, Vazdar, Katarina, Vazdar, Mario, Đaković, Marijana, Mikecin, Ana-Matea, Kralj, Marijeta, Malnar, Martina, Hećimović, Silva, Habuš, Ivan
Format: Article
Language:English
Subjects:
2-Aminoimidazolone
Antiproliferative activity
Guanidine
Rearrangement
β-Lactam
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Summary: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. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2015.10.048