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Volumn 45, Issue 7, 1989, Pages 1905-1928

Molecular modeling of γ-lactam analogues of β-lactam antibacterial agents: synthesis and biological evaluation of selected penem and carbapenem analoques

Author keywords

[No Author keywords available]

Indexed keywords

7 [2 (2 AMINO 4 THIAZOLYL) 2 METHOXYIMINOACETAMIDO] 3 METHYL 8 OXO 4 THIA 1 AZABICYCLO[3.3.0]OCT 2 ENE 2 CARBOXYLIC ACID; AMOXICILLIN; CARBAPENEM DERIVATIVE; CEFALORIDINE; GAMMA LACTAM DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0024597718     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(01)80055-7     Document Type: Article
Times cited : (56)

References (97)
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  • 34
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    • 26th Interscience Conference on Antimicrobial Agents and Chemotherapy, New Orleans, Louisiana, No. 602.
    • Abstracts
    • Indelicato1    Pasini2
  • 66
    • 84918156048 scopus 로고    scopus 로고
    • Kennard, O.; Watson, D.G.; Allen, F.H.; Isaacs, N.W.; Motherwell, W.D.S.; Pettersen, R.C.; Town, W.G.; “Molecular Structures and Dimensions” A1 Cambridge Data Centre: Cambridge U. K.
  • 71
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    • Tripos Associates, St. Louis, MO
    • (1985) SYBYL Manual
  • 88
    • 0000614494 scopus 로고
    • The bridgehead hydrogen atom (H5) was assigned to have a cis configuration to carboxylate at C2 by analogy to similar systems, and ref. 31.
    • (1985) Tetrahedron Lett. , vol.26 , pp. 647
    • Nagai1    Sato2
  • 90
    • 84914319003 scopus 로고
    • A GENERAL ASYMMETRIC CYCLIZATION. ASYMMETRIC SYNTHETHIS OF OPTICALLY ACTIVE 2-OXO-5-PYRROLIDINEACETIC ACID DERIVATIVES
    • Derived from the corresponding nitrile.
    • (1976) Chemistry Letters , pp. 1283
    • Wakabayashi1    Kato2    Watanabe3
  • 96
    • 37049076881 scopus 로고
    • Synthesis of ?-lactam analogues of carbapenems with substituted-thio groups at the C-3 position
    • After completion of this investigation, a report appeared describing the synthesis of related γ-lactam C-3 sulfides and sulfones:, The most active γ-lactam analogue of carbapenems reported by the Takeda group was the 5-epimer, i. e., a compound with the nucleus (5R,7S)-8-oxo-1-azabicyclo[3.3.0]oct-2-ene-2-carboxylate. This compound exhibited MICs as low as 6.25 mg/ml against Proteus mirabilis. The comparable activity of this epimer to that of the (5S,7S) compounds reported by the Takeda group is understandable in terms of molecular modeling recently done by us. Optimization of a (5S,7S)-7-formamido-8-oxo-1-azabicyclo[3.3.0]oct-2-ene-2-carboxylic acid model by MINDO/3 and fitting by SYBYL showed a root mean square distance of 0.25 Å to cephaloridine and 0.50 Å to amoxycillin. These fits, which are as good as for the best 5S,7S isomer in Table I, are illustrated below in stereo.
    • (1988) Journal of the Chemical Society, Perkin Transactions 1 , pp. 2345
    • Hashiguchi1    Natsugari2    Ochiai3
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    • Difference NOE measurements (although not obtainable on all derivatives) wereconsistent with these assignments.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.