Synthesis and biological evaluation of some new β-lactam-triazole hybrids

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• 作者：Aliasghar Jarrahpour ; Pouria Shirvani ; Véronique Sinou…
• 关键词：β ; Lactam ; N ; endo ; 5 ; norbornene ; 2 ; 3 ; dicarboxyloylglycine ; Triazole hybrids ; P. falciparum
• 刊名：Medicinal Chemistry Research
• 出版年：2016
• 出版时间：January 2016
• 年：2016
• 卷：25
• 期：1
• 页码：149-162
• 全文大小：1,250 KB
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• 作者单位：Aliasghar Jarrahpour (1)
  Pouria Shirvani (1)
  Véronique Sinou (2)
  Christine Latour (2)
  Jean M. Brunel (3)
  
  1. Department of Chemistry, College of Sciences, Shiraz University, Shiraz, 71454, Iran
  2. UMR-MD3 Relation hôte-parasites, Physiopathologie & Pharmacologie, Faculté de pharmacie, Aix-Marseille Université, Bd Jean Moulin, 13385, Marseille, France
  3. Centre de Recherche en Cancérologie de Marseille (CRCM), CNRS, UMR7258, Institut PaoliCalmettes, Inserm, U1068, Faculté de Pharmacie, Aix-Marseille Université, UM 105, 27 Bd Jean Moulin, 13385, Marseille Cedex 05, France
  
• 刊物主题：Pharmacology/Toxicology; Biochemistry, general; Cell Biology;
• 出版者：Springer US
• ISSN：1554-8120

文摘

A series of novel β-lactams was synthesized from different imines and a special ketene derived from N-endo-5-norbornene-2,3-dicarboxyloylglycine 1 via the [2 + 2] ketene imine cycloaddition. Then, β-lactams 3a–h were treated with 1-azido-4-nitrobenzene 4 to afford β-lactam-triazole hybrids 5a–h. Of the twenty-three β-lactams tested against chloroquine-resistant P. falciparum K14 strain, 3a and 3d showed IC₅₀ < 20 µM, while 3j, 3m, 5a–5f exhibited IC₅₀ < 50. These newly synthesized β-lactams were also tested against S. aureus, E. coli, P. aeruginosa, C. albicans and C. glabrata and showed no activity below 125 µg/mL. Keywords β-Lactam N-endo-5-norbornene-2,3-dicarboxyloylglycine Triazole hybrids P. falciparum