• Title/Summary/Keyword: 6-Exomethylene penam

Search Result 8, Processing Time 0.018 seconds

Synthesis of 6-Exomethylene Penams Derivatives (6-엑소메칠렌 펜남 유도체의 합성)

  • 임채욱;윤상배;김용현;정미량;임철부
    • YAKHAK HOEJI
    • /
    • v.47 no.5
    • /
    • pp.288-292
    • /
    • 2003
  • 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.

Synthesis and $\beta$-lactamase inhibitory activity of 6-exomethylene penamsulfone derivatives - II (Synthesis of 6-exomethylene penamsulfone derivatives)

  • Yim, Chul-Bu;Youm, Jeong-Rok;Im, Chae-Uk;Park, Hee-Suk;Oh, Jeong-Suk;Park, Kye-Hwan
    • Proceedings of the Korean Society of Applied Pharmacology
    • /
    • 1996.04a
    • /
    • pp.160-160
    • /
    • 1996
  • $\beta$-Lactam계 항생제 내성균의 문제를 해결할 수 있는 $\beta$-lactamase억제제의 개발을 위해서, cephalosporinase에 특히 높은 억제활성을 갖는 새로운 6-exomethylene penamsulfones 화합물을 합성하였다. Dibromopenamsulfone과 thioalkyl triazole-4-carboxaldehyde을 반응시키고, acetic anhydride와 Zn으로 처리하여 E-form과 Z-form의 6-exomethylene penam sulfones을 합성하였다. 이것을 AlCl$_3$으로 deprotection시킨 후, NaOH로 처리하여 6-exomethylene penamsulfone의 Na-salt form으로 목적물질을 합성하였다.

  • PDF

Synthesis of 6-Exomethylene Penam Derivatives (6-엑소메칠렌 펜남 유도체의 합성)

  • 임채욱;박희석;이현수;임철부
    • YAKHAK HOEJI
    • /
    • v.44 no.2
    • /
    • pp.128-134
    • /
    • 2000
  • The synthesis of new 6-exomethylene penams with triazole ring was described. The 6,6-dibromopenam 5 was treated with $CH_3$MgBr and carbaldehyde 4 to afford the 6-bromo-6-(1-hydroxy-1-methyl)penicillanate 6, which was reacted with acetic anhydride to give acetoxy compound 7. The deacetobromination of 7 with zinc and acetic acid gave 6-exomethylenpenams, Z-isomer 8 and E-isomer 9, which were oxidized to sulfones 10 and 11 by m-CPBA. The p-methoxybenzyl compounds 6~11 were deprotected by AlCl$_3$ and neutralized to give the sodium salts 12~17.

  • PDF

Synthesis of 6-Triazole Exomethylenepenams Derivatives (6-트리아졸 엑소메칠렌펜남 유도체의 합성)

  • 김연숙;오정석;임채욱;임철부
    • YAKHAK HOEJI
    • /
    • v.48 no.5
    • /
    • pp.303-308
    • /
    • 2004
  • The synthesis of new 6-triazole exomethylenepenams 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 and 9, which were oxidized to sulfones 10 and 11 by m-CPBA. The p-methoxybenzyl compounds 6-11 were deprotected by AlCl$_3$ and neutralized to give the sodium salts 12-17.

Synthesis of 6-Exomethylene Penams with Benzothiazole Ring (Benzothiazole고리가 있는 6-엑소메칠렌 펜남 유도체의 합성)

  • 임채욱;박희석;김승재;임철부
    • YAKHAK HOEJI
    • /
    • v.46 no.5
    • /
    • pp.307-312
    • /
    • 2002
  • The synthesis of new 6-exomethylene penams with benzothiazole ring was described. The 6,6-dibromopenam 5 was treated with $CH_3$MgBr and carbaldehyde 4 to afford the 6-bromo-6-(1-hydroxy-1-methyl)penicillanate 6, which was reacted with acetic anhydride to give acetoxy compound 7. The deacetobromination of acetoxy compound 7 with zinc and acetic acid gave 6-exomethylene penams, Z-isomer 8 and E-isomer 9, which was oxidized to sulfones 10 by m-CPBA. The p-methoxybenzyl compounds 6~10 were deprotected by AlCl$_3$ and neutralized to give the sodium salts 11~15.

Synthesis and $\beta$-lactamase inhibitory activity of 6-exomethylene penamsulfone derivatives-II (Synthesis of 6-exomethylene penamsulfone derivatives)

  • Park, Hee-Suk;Yoon, Sang-Bae;Chaeuk Im;Yim, Chul-Bu
    • Proceedings of the Korean Society of Applied Pharmacology
    • /
    • 1997.04a
    • /
    • pp.71-71
    • /
    • 1997
  • $\beta$-lactamase를 생성하는 균들이 $\beta$-lactam계 항생제를 분해하여 불활성화 시키므로 이를 해결하기 위하여 그 효소에 대하여 억제활성을 나타내는 새로운 6-exomethylenepenamsulfone화합물들을 합성하였다. Dibromopenamsulfone과 heterocyclic ring을 함유한 thioethyl triazole-4-carboxaldehyde를 반응시키고, acetic anhydride와 Zn으로 처리하여 E-form과 Z-form의 6-exomethylene penmsulfones을 합성하였다. 이것을 AlCl$_3$로 처리하여 deprotection시킨 후, NaHCO$_3$로 처리하여 6-exomethylene penam sulfones의 Na-salt의 형태로 목적물질을 합성하였다.

  • PDF

Synthesis of 6-Exomethylene Penam Derivatives with Triazole Ring (트리아졸환 함유 6-엑소메칠렌 펜남 유도체의 합성)

  • 임채욱;오정석;임철부
    • YAKHAK HOEJI
    • /
    • v.45 no.2
    • /
    • pp.140-146
    • /
    • 2001
  • The synthesis of new 6-exomethylene penams with triazole ring for $\beta$-lactamase inhibitor was described. 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 anhydride to give acetoxy compound 8. The deacetoxybromination of 8 with zinc and acetic acid gave 6-exomethylenepenams, Z-isomer 9 and E-isomer 10, which were oxidized to sulfones 11 and 12 by m-CPBA. The p-methoxybenzyl compounds 9~12 were deprotected by AIC1$_3$and neutralized to give the sodium salts 13~16.

  • PDF

[ β ]-Lactamase Inhibitory Activities of New 6-tricyclic Substituted Exomethylene Penam Sulfones

  • Lee, Su-Jin;Kim, Hyun-Jin;Sheen Yhun Y.;Lee, Kwan-Soon;ParkChoo, Hea-Young
    • Biomolecules & Therapeutics
    • /
    • v.14 no.4
    • /
    • pp.220-225
    • /
    • 2006
  • Derivatives of penicillanic acid sulfones are known to be irreversible inhibitors of $\beta$-lactamase. Eight 6-tricyclic methylene penicillanic acid sulfones were prepared, and their $\beta$-lactamase inhibitory activities were evaluated against $\beta$-lactamase types I, II, III and IV. Among the tricycles attached to 6-exomethylenepenam sulfones, thiazolobenzimidazole(12a-12b), fluorene(12c), and carbazole(12e), showed inhibitory activity on type I, II and III $\beta$-lactamase. But phenanthrene(12d), and anthracene(12f-12h) derivatives showed little $\beta$-lactamase inhibitory activity. The synergic effects of the selected compound(l2b) in 1:4 combination with piperacillin showed some protection to piperacillin for the resistant strains of E. coli DC2 and P. aeruginosa 1771.