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Volumn , Issue 20, 2004, Pages 2332-2333

Penicillins as β-lactamase-dependent prodrugs: Enabling role of a vinyl ester exocyclic to the lactam ring

Author keywords

[No Author keywords available]

Indexed keywords

BETA LACTAM; BETA LACTAMASE; ESTER; PENICILLIN DERIVATIVE; PRODRUG; VINYL DERIVATIVE;

EID: 8644249388     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b409517k     Document Type: Article
Times cited : (9)

References (18)
  • 5
    • 9144223532 scopus 로고    scopus 로고
    • Patent number WO 99/33837, 1999
    • (b) J. D. Buynak, Patent number WO 99/33837, 1999;
    • Buynak, J.D.1
  • 8
    • 9144247554 scopus 로고    scopus 로고
    • note
    • -1 more stable than its isomeric form C.
  • 9
    • 9144233370 scopus 로고    scopus 로고
    • note
    • In the case of B1, steric hindrance by the t-butyl group blocks addition of the nucleophile to the ester carbonyl, which is the rate-determining step.
  • 10
    • 0020539331 scopus 로고
    • A parallel for this is found in the intramolecular nucleophilic addition that occurs within the β-lactam-ring-cleaved structure derived from 6(Z)-acetylmethylenepenicillanic acid (a potent β-lactamase inhibitor): M. Arisawa and S. Adam, Biochem. J., 1983, 211, 447-454.
    • (1983) Biochem. J. , vol.211 , pp. 447-454
    • Arisawa, M.1    Adam, S.2
  • 11
    • 0029050953 scopus 로고
    • 6(Z)-t-butoxycarbonylmethylenepenicillanate and 6(Z)- methoxycarbonylmethylenepenicillanate have been found to be β-lactamase substrates (the corresponding sulfones are inhibitors), however, the fate of the β-lactam-ring-cleaved structures was not reported on: (a) J. D. Buynak, B. Geng, B. Bachmann and L. Hua, Bioorg. Med. Chem. Lett., 1995, 5, 1513-1518;
    • (1995) Bioorg. Med. Chem. Lett. , vol.5 , pp. 1513-1518
    • Buynak, J.D.1    Geng, B.2    Bachmann, B.3    Hua, L.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.