Synthesis and structure-activity relationships in the cefpirome series. I. 7-(2-(2-Aminothiazol-4-yl)-2-(Z)-oxyiminoacetamido)-3-((substituted-1-pyridinio)methyl)-ceph-3-em-4-carboxylates.

DOI PubMed

書誌事項

タイトル別名
  • I. 7-[2-(2-AMINOTHIAZOL-4-YL)-2-(Z)-OXYIMINOACETAMIDO]-3-[(SUBSTITUTED-1-PYRIDINIO)METHYL]-CEPH-3-EM-4-CARBOXYLATES

この論文をさがす

説明

7-[2-(2-Aminothiazol-4-yl)-2-(Z)-oxyiminoacetamido]-3-[(substituted-1-pyridinio)methyl]ceph-3-em-4-carboxylates II are a group of β-lactam antibiotics with extraordinary high antibacterial activity. The promising member of this group, cefpirome (HR 810, II-1) is a candidate for clinical use. Synthetic pathways to II starting from cefotaxime derivatives I or 7-aminocephalosporanic acid (7-ACA) are described. A preferred method for the conversion of I to II or 7-ACA to precursors III respectively employs iodotrimethylsilane and an excess of the pyridine base. Structure-activity studies reveal an optimum overall activity in the series of pyridines with fused saturated and unsaturated rings or cyclopropyl- and alkoxy substituents. Favorable oxyimino substituents are methyl, ethyl, difluoromethyl and carbamoylmethyl groups. Acidic substituents lead to decreased activity against Staphylococcus aureus SG 5.11. Introduction of halogen in the thiazole nucleus causes improvement of activity against the K1 β-lactamase producing Klebsiella aerogenes 1082 E strain.

収録刊行物

  • The Journal of Antibiotics

    The Journal of Antibiotics 41 (10), 1374-1394, 1988

    公益財団法人 日本感染症医薬品協会

キーワード

詳細情報 詳細情報について

  • CRID
    1390001204151354624
  • NII論文ID
    130003501348
  • DOI
    10.7164/antibiotics.41.1374
  • COI
    1:CAS:528:DyaL1MXlsVemtQ%3D%3D
  • ISSN
    18811469
    00218820
  • PubMed
    3142844
  • 本文言語コード
    en
  • 資料種別
    journal article
  • データソース種別
    • JaLC
    • Crossref
    • PubMed
    • CiNii Articles
  • 抄録ライセンスフラグ
    使用不可

問題の指摘

ページトップへ