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

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• 作者：Tonko Dražić^a ; ^{tdrazic@irb.hr" class="auth_mail" title="E-mail the corresponding author} ; Katarina Vazdar^a ; Mario Vazdar^a ; Marijana Đaković^b ; Ana-Matea Mikecin^a ; Marijeta Kralj^a ; Martina Malnar^a ; Silva Hećimović^a ; Ivan Habu&scaron ; ^a
• 关键词：β-Lactam ; Guanidine ; 2-Aminoimidazolone ; Rearrangement ; Antiproliferative activity
• 刊名：Tetrahedron
• 出版年：2015
• 出版时间：9 December 2015
• 年：2015
• 卷：71
• 期：49
• 页码：9202-9215
• 全文大小：1271 K

文摘

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.