Archives of Pharmacal Research

  • 제20권6호
  • /
  • Pages.647-651
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  • 1997
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  • 0253-6269(pISSN)
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  • 1976-3786(eISSN)
대한약학회 (The Pharmaceutical Society of Korea)
권호 표지

Synthesis of 6-[1-[4-(Benzoxazol-2-yl)thiobuthyl]-1,2,3-triazole-4-yl]methylenepenam as ${\beta}$-Lactamase Inhibitors

  • 발행 : 1997.12.01
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초록

The 6, 6-dibromopenam 6 was treated with $CH_{3}/MgBr$ and carbaldehyde 5 to afford the 6-bromo-6-(1-hydroxy-1-methyl)penicillanate 7, which was reacted with acetic anhybride to give acetoxy compound 8. The deacetobromination of 8 with zinc and acetic acid gave 6-exomethylenpenams, Z-isomer 9 and E-isomer 10, which were oxidized to sulfones 11 and 12 by m-CPBA. The p-methoxybenzyl compounds were deprotected by $AlCl_{3}$ and neutralized to give the sodium salts 13, 14, and 15.

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참고문헌

  1. 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.
  2. 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.
  3. J. Am. Chem. Soc. v.77 The acid-catalyzed reaction of alkyl azides upon carbonyl compounds Boyer,J.H.;Hamer,J.
  4. Eur. Pat. Appl. β-(Substituted methylene) penems Broom,N.J.P.;Brooks,G.;Clark,B.P.
  5. Tetrahedron Lett. v.27 Synthesis of a potent β-lactamase inhibitor 1,1-dioxo-6(2-pyridyl )methylenepenicillanic acid and its reaction with sodium methoxide Chen,Y.L.;Chant,C.W.;Hedberg,K.
  6. J. Antibiotics v.40 Structure-activity relationships of 6-(heterocyclyl)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.
  7. Antimicrob. Agents. Chemother. v.14 CP-45,899, a β-lactamase inhibitor that extends the actibacterial spectrum of β-lactams; initial bacteriological characterization English,A.R.;Retsema,J.A.;Girard,A.E.;Lynch,J.E.;Barth,W.E.
  8. Eur. Pat. Appl. EP 139047 6,6-Dibromopenicillanic acid 1,1-dioxide Kapur,J.C.;Fasel,H.P.
  9. Synthesis Synthesis of 2β-azidomethylpenicillin-1,1-dioxides and 3β-azido-3α-methylcepham-1,1-dioxides Micetich,R.G.;Maiti,S.N.;Spevak,P.
  10. J. Med. Chem. v.30 Synthesis and β-lactamase inhabitory properties of 2β-[(1,2,3-triazol-1-yl)methyl]-2α-methylpenam-3α-carboxyl acid 1.1-dioxide and related triazolyl derivatives Micetich,R.G.;Maiti,S.N.;Spevak,P.;Hall,T.W.;Tamabe,S.;Ishida,N.;Tanaka,M.;Yamazaki,T.;Nakai,A.;Ogawa,K.
  11. Heterocycles v.31 2,4,6,-Tripyridino-1,3,5-trichloride, a new and mild esterification agent for prepartion of penicillin esters Murakam,M.;Hajima,M.;Takami,F.;Yoshioka,M.
  12. Yakhak Hoeji v.41 no.4 Comparison of the Activities of Novel β-Lactamase Inhibitors, 6-Exomethylene Penamsulfones with Other β-Lactamase Inhibitors as Combined with -Lactam Antibiotics Park,K.W.;Kim,K.H.;Kim,M.Y.;Im,C.U.;Yim,C.B.
  13. Org. Synthesis v.4 Propiolaldehyde Sauer,J.C.
  14. Biochem. J. v.199 The inhibition of β-lactamases from gram-negative bacteria by clavulanic acid Reading,C.;Farmer,T.