YAKHAK HOEJI (약학회지)

The Pharmaceutical Society of Korea (대한약학회)
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Synthesis of 6-Exomethylene Penams Derivatives

6-엑소메칠렌 펜남 유도체의 합성

  • 임채욱 (중앙대학교 약학대학 의약화학 교실) ;
  • 윤상배 (중앙대학교 약학대학 의약화학 교실) ;
  • 김용현 (중앙대학교 약학대학 의약화학 교실) ;
  • 정미량 (중앙대학교 약학대학 의약화학 교실) ;
  • 임철부 (중앙대학교 약학대학 의약화학 교실)
  • Published : 2003.10.01
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Abstract

The synthesis of new 6-exomethylene penams with substituted triazole ring was described. The 6,6-dibromopenam 5 was reacted with $CH_3$MgBr and substituted triazole 4 to afford the 6-bromo penicillanate 6, which was treated with acetic anhydride to give acetoxy compound 7. The deacetobromination of acetoxy compound 7 with zinc and acetic acid gave 6-exomethylene penams 8, which was oxidized to sulfones 9 by m-CPBA. The p-methoxybenzyl compounds 6∼9 were deprotected by AlCl$_3$ and neutralized to give the sodium salts 10∼13.

Keywords

References

  1. Science v.257 The crisis Antibiotic Resistacne Neu,H.C. https://doi.org/10.1126/science.257.5073.1064
  2. Antimicrob. Agents Chemother v.11 A β-lactam from Streptomyces clavulingerus Reading,C.;Cole,M. https://doi.org/10.1128/AAC.11.5.852
  3. Antimicrob. Agents. Chemother v.14 CP-45,899, a β-lactamse inhibitor that extends the antibacterial of β-lactams; initial bacteriological characterization English,A.R.;Retsema,J.A.;Girard,A.E.;Lynch,J.E.;Barb,W.E. https://doi.org/10.1128/AAC.14.3.414
  4. J. Med. Chem. v.30 Synthesis and β-lactamase inhibitory properties of 2 β-[(1,2,3-triazol-1-y)methyl]-2α-methylpenam-3α-carboxylic acid 1,1-dioxide and related triazolyl derivatives Micetich,R.G.;Maiti,S.N.;Spevak,P.;Hall,T.W.;Yamabe,S.;Ishida,N.;Tanake,M.;Yamazaki,T.;Nakai,A.;Ogawa,K. https://doi.org/10.1021/jm00391a032
  5. Tetrahedron Lett. v.27 Synthesis of a potent β-lactamase inhibitor 1,1-dioxo-6-(2-pyridyl)methyl-enepenicillanic acid and its reaction with sodium methoxide Chen,Y.L.;Chang,C.W.;Hedberg,K. https://doi.org/10.1016/S0040-4039(00)84819-4
  6. J. Antibiotics v.44 6-(Substituted methylene) penems, potent broad spectrum inhibitors of bacterial β-lactamase V. Chiral 1,2,3,-triazolyl derivatives Bennett,I.S.;Brooks,G.;Broom,N.J.P.;Calvert,S.H.;Coleman,K.;Francois,I. https://doi.org/10.7164/antibiotics.44.969
  7. J. Antibiotics v.44 6-(Substituted methylene) penems, potent broad spectrum inhibitors of bacterial β-lactamase Ⅲ. Structure-activity relationships of the 5-membered heterocyclic derivatives Bennett,I.;Broom,N.J.P.;Bruton,G.;Calvert,S.;Clarke,B.P.;Coleman,K.;Edmondson,R.;Edwards,P.;Jones,D.;Osborne,N.F.;Walker,G. https://doi.org/10.7164/antibiotics.44.331
  8. Eur. Pat. Appl. v.321187 β-(Substituted methylene) penems Broom,N.J.P.;Brooks,G.;Clark,B.P.
  9. J. Antibiotics v.40 Structure-activity relationships of 6-(heterocycly) methylene penam sulfones; a new class of β-lactamase inhibitors Chen,Y.L.;Chang,C.W.;Hedberg,K.;Guarino,K.;Welch,W.M.;Kiessling,L. https://doi.org/10.7164/antibiotics.40.803
  10. J. Am. Chem. Soc. v.77 The acid-catalyzed reaction of alkyl azides upon carbonyl compounds Boyer,J.H.;Hamer,J. https://doi.org/10.1021/ja01609a045
  11. In Oranic systheses Collective volume Ⅳ, Robjohn Sauer,J.C.