7-アミノデアセトキシセファロスポラン酸の脱硫反応

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書誌事項

タイトル別名
  • Desulfurization of 7-Aminodeacetoxycephalosporanic Acid
  • 7 アミノデアセトキシセファロスポランサン ノ ダツリュウ ハンノウ

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説明

The Raney nickel desulfurization of 7-aminodeacetoxycephalosporanic acid (7-ADCA) was investigated to obtain 2-(3-amino-2-oxo-1-azetidinyl)-3-methyl-2-butenoic acid derivative (3a), a useful intermediate in a synthesis of monobactam compounds. The desulfurization of 7-ADCA gave a monocyclic β-lactam 3a and an unexpected 5-oxazolone derivative 5a. Compound 5a would be formed by the lactonization of alanyldehydrovaline derivative 4 derived from the hydrogenolytic cleavage of N-C4 bond of β-lactam ring in 7-ADCA. Similarly the desulfurization of cephalexin with Raney nickel gave the monocyclic β-lactam 3b and the 5-oxazolone derivative 5b. Compound 3a on treatment by the reported procedure gave 3-amino-2-azetidinone-1-sulfonic acid (7). Monobactam compounds 8 were obtained by acylation or arylation of 7. None of compounds 8a-e showed in vitro antibacterial activity against gram-positive and -negative bacteria.

収録刊行物

  • 薬学雑誌

    薬学雑誌 104 (3), 302-307, 1984

    公益社団法人 日本薬学会

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