Calixcephems: clustered cephalosporins analogous to calixpenams as novel potential anti-MRSA agents

Two novel clusters of cephalosporin based on calixarene were synthesized directly or by ring expansion of the penicillin arms of calixpenams to the corresponding cephem arms via sulfoxide intermediates. Antibiotic tests showed that calixcephems have a noteworthy increase in antibacterial activity against methicillin-resistant strains of Staphylococcus aureus (MRSA) with respect to parent calixpenams and their corresponding single cephems.

Calixcephems: clustered cephalosporins analogous to calixpenams as novel potential anti-MRSA agents

Two novel clusters of cephalosporin based on calixarene were synthesized directly or by ring expansion of the penicillin arms of calixpenams to the corresponding cephem arms via sulfoxide intermediates. Antibiotic tests showed that calixcephems have a noteworthy increase in antibacterial activity against methicillin-resistant strains of Staphylococcus aureus (MRSA) with respect to parent calixpenams and their corresponding single cephems.

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  • 1. Leeb, M. Nature 2004, 431, 892–893.
  • 2. Hansmann, D.; Bullen, M. M. Lancet 1967, 2, 264–265.
  • 3. Kluytmans, J.; Van Belkum, A.; Verbrugh, H. Clin. Microbiol. Rev. 1997, 10, 505–520.
  • 4. Murray, B. E.; Moellering, R. C. Annu. Rev. Med. 1981, 32, 559–581.
  • 5. Tan, Q.; Song, Q.; Wei, D. Enzyme Microb. Tech. 2006, 39, 1166–1172.
  • 6. Morin, R. B.; Jackson, B. G.; Mueller, R. A.; Lavagnino, E. R.; Scanlon, W. B.; Andrews, S. L. J. Am. Chem. Soc. 1963, 85, 1896–1897.
  • 7. Morin, R. B.; Gorman, M. β -Lactam Antibiotics, Chemistry and Biology; Academic Press: New York, NY, USA, 1981.
  • 8. Singh, J.; Arrieta, A. C. Semin. Pediatr. Infect. Dis. 1999, 10, 14–22.
  • 9. Kalman, D.; Barriere, S. L. Tex. Heart. Inst. J. 1990, 17, 203–215.
  • 10. Garcia-Rodriguez, J. A.; Bellido, J. L. M.; Sanchez, J. E. G. Int. J. Antimicrob. Agents 1995, 5, 231–243.
  • 11. Nasuhi Pur, F.; Akbari Dilmaghani, K. Turk. J. Chem. 2014, 38, 288–296.
  • 12. Nasuhi Pur, F.; Akbari Dilmaghani, K. J. Coord. Chem. 2014, 67, 440–448.
  • 13. de Koning, J. J.; Kooreman, H. J.; Tan, H. S.; Verweij, J. J. Org. Chem. 1975, 40, 1346–1347.
Turkish Journal of Chemistry-Cover
  • ISSN: 1300-0527
  • Yayın Aralığı: Yılda 6 Sayı
  • Yayıncı: TÜBİTAK
Sayıdaki Diğer Makaleler

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QSAR study of chalcone derivatives as anti-Leishmania agents

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Synthesis of novel triazoles bearing 1,2,4-oxadiazole and phenylsulfonyl groups by 1,3-dipolar cycloaddition of some organic azides and their biological activities

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Ultrarapid catalytic reduction of some dyes by reusable novel erythromycin-derived silver nanoparticles

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Graphene oxide magnetite nanocomposite as an efficient and magnetically separable adsorbent for methylene blue removal from aqueous solution

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Rosmarinic acid: a potent carbonic anhydrase isoenzymes inhibitor

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N-Heterocyclic carbene (NHC) palladium(II) complexes bearing chiral oxazoline ligands and their catalytic activities in allylic alkylation reactions

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Effects of functional groups of triple bonds containing molecules on nickel electroplating

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Simultaneous determination of dexpanthenol, lidocaine hydrochloride, and mepyramine maleate in combined pharmaceutical gel by capillary electrophoresis

Gülden Başmakçi AKYIL, Hayriye Eda Şatana KARA, Sezen Yarimkaya BAŞ, Nusret ERTAŞ, Nilgün GÜNDEN GÖĞER

Synthesis, anticandidal activity, and cytotoxicity of some thiazole derivatives with dithiocarbamate side chains

Leyla YURTTAŞ, Yusuf ÖZKAY, Fatih DEMİRCİ, Gamze GÖGER, Şafak Ulusoylar YILDIRIM, Usama ABU MOHSEN, Ömer ÖZTÜRK, Zafer Asım KAPLANCIKLI