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Volumn 13, Issue 1, 1996, Pages 70-75

Acyloxymethyl as a drug protecting group. Part 3. Tertiary O-amidomethyl esters of penicillin G: Chemical hydrolysis and anti-bacterial activity

Author keywords

Antibacterial activity; Carboxylic acids; Hydrolysis kinetics; Mechanism of hydrolysis; O amidomethylation; Penicillin G; Prodrugs

Indexed keywords

PENICILLIN G DERIVATIVE; PRODRUG;

EID: 0029865020     PISSN: 07248741     EISSN: None     Source Type: Journal    
DOI: 10.1023/A:1016077200460     Document Type: Article
Times cited : (20)

References (14)
  • 1
    • 0001197429 scopus 로고
    • Design of Bioreversible Drug Derivatives and the Utility of the Double Prodrug Concept
    • E.B. Roche (Ed.) Pergamon Press, New York
    • H. Bundgaard. Design of Bioreversible Drug Derivatives and the Utility of the Double Prodrug Concept. In E.B. Roche (Ed.), Bioreversible Carriers in Drug Design: Theory and Application; Pergamon Press, New York, 1987; pp. 13-94.
    • (1987) Bioreversible Carriers in Drug Design: Theory and Application , pp. 13-94
    • Bundgaard, H.1
  • 2
    • 37049081323 scopus 로고
    • Triazene drug metabolites. 4. Kinetics and mechanism of the decomposition of 1-aryl-3-benzoyloxymethyl-3-methyltriazenes in mixed aqueous-organic solvents
    • J.N. Iley, R. Moreira, and E. Rosa. Triazene drug metabolites. 4. Kinetics and mechanism of the decomposition of 1-aryl-3-benzoyloxymethyl-3-methyltriazenes in mixed aqueous-organic solvents. J. Chem. Soc. Perkin Trans. 2: 1503-1508 (1987).
    • (1987) J. Chem. Soc. Perkin Trans. 2 , pp. 1503-1508
    • Iley, J.N.1    Moreira, R.2    Rosa, E.3
  • 3
    • 6844251363 scopus 로고
    • Pro-drugs as drug delivery systems. XVI. Novel water-soluble pro-drugs types for chlorzoxazone by esterification of the N-hydroxymethyl derivative
    • M. Johansen and H. Bundgaard. Pro-drugs as drug delivery systems. XVI. Novel water-soluble pro-drugs types for chlorzoxazone by esterification of the N-hydroxymethyl derivative. Arch. Pharm. Chemi, Sci. Ed. 9: 43-54 (1981).
    • (1981) Arch. Pharm. Chemi, Sci. Ed. , vol.9 , pp. 43-54
    • Johansen, M.1    Bundgaard, H.2
  • 4
    • 0025913143 scopus 로고
    • Prodrugs of peptides. 11. Chemical and enzymatic hydrolysis kinetics of N-acyloxymethyl derivatives of a peptide-like bond
    • H. Bundgaard and G.J. Rasmussen. Prodrugs of peptides. 11. Chemical and enzymatic hydrolysis kinetics of N-acyloxymethyl derivatives of a peptide-like bond. Pharm. Res. 8: 1238-1242 (1991).
    • (1991) Pharm. Res. , vol.8 , pp. 1238-1242
    • Bundgaard, H.1    Rasmussen, G.J.2
  • 5
    • 0021185679 scopus 로고
    • Phenytoin prodrugs. III. Water-soluble prodrugs for oral and parenteral use
    • S.A. Varia; S. Schuller; K.B. Sloan, and V.J., Stella. Phenytoin prodrugs. III. Water-soluble prodrugs for oral and parenteral use. J. Pharm. Sci. 73: 1068-1073 (1984).
    • (1984) J. Pharm. Sci. , vol.73 , pp. 1068-1073
    • Varia, S.A.1    Schuller, S.2    Sloan, K.B.3    Stella, V.J.4
  • 6
    • 0021992828 scopus 로고
    • Prodrugs of 5-fluorouracil. IV. Hydrolysis kinetics, bioactivation and physicochemical properties of various N-acyloxymethyl derivatives of 5-fluorouracil
    • A. Buur, H. Bundgaard, and E. Falch. Prodrugs of 5-fluorouracil. IV. Hydrolysis kinetics, bioactivation and physicochemical properties of various N-acyloxymethyl derivatives of 5-fluorouracil. Int. J. Pharm. 24: 43-60 (1985).
    • (1985) Int. J. Pharm. , vol.24 , pp. 43-60
    • Buur, A.1    Bundgaard, H.2    Falch, E.3
  • 7
    • 0023516755 scopus 로고
    • Prodrugs as drug delivery systems. 74. Facile hydrolysis of N-(acyloxymethyl)amide derivatives and implications for the design of prodrugs of NH-acidic compounds and of carboxylic acids
    • H. Bundgaard and N.M. Nielsen. Prodrugs as drug delivery systems. 74. Facile hydrolysis of N-(acyloxymethyl)amide derivatives and implications for the design of prodrugs of NH-acidic compounds and of carboxylic acids. Acta Pharm. Suec. 24: 233-246 (1987).
    • (1987) Acta Pharm. Suec. , vol.24 , pp. 233-246
    • Bundgaard, H.1    Nielsen, N.M.2
  • 8
    • 37049084026 scopus 로고
    • Acyloxymethyl as a drug protecting group. Kinetics and mechanism of the hydrolysis of N-acyloxymethylbenzamides
    • J. Iley, R. Moreira, and E. Rosa. Acyloxymethyl as a drug protecting group. Kinetics and mechanism of the hydrolysis of N-acyloxymethylbenzamides. J. Chem. Soc. Perkin Trans. 2: 563-570 (1991).
    • (1991) J. Chem. Soc. Perkin Trans. 2 , pp. 563-570
    • Iley, J.1    Moreira, R.2    Rosa, E.3
  • 9
    • 0018712807 scopus 로고
    • Orally active esters of cephalosporin antibiotics. 3. Synthesis and biological properties of amino-acyloxymethyl esters of [D-(-)-mandelamido]-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-3-cephem-4- carboxylic acid
    • W.J. Wheeler, P.A. Preston, W.E. Wright, G.W. Huffman, H.E. Osborn, and D.P. Howard. Orally active esters of cephalosporin antibiotics. 3. Synthesis and biological properties of amino-acyloxymethyl esters of [D-(-)-mandelamido]-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-3-cephem-4- carboxylic acid. J. Med. Chem. 22: 657-661 (1979).
    • (1979) J. Med. Chem. , vol.22 , pp. 657-661
    • Wheeler, W.J.1    Preston, P.A.2    Wright, W.E.3    Huffman, G.W.4    Osborn, H.E.5    Howard, D.P.6
  • 10
    • 0001596755 scopus 로고
    • The mechanisms of reactions of β-lactam antibiotics
    • M.I. Page. The mechanisms of reactions of β-lactam antibiotics. Adv. Phys. Org. Chem. 23: 165-270 (1987).
    • (1987) Adv. Phys. Org. Chem. , vol.23 , pp. 165-270
    • Page, M.I.1
  • 11
    • 0027971217 scopus 로고
    • A new direct synthesis of tertiary N-acyloxymethylamide prodrugs of carboxylic acid drugs
    • R. Moreira, E. Mendes, T. Calheiros, M.J. Bacelo, and J. Iley. A new direct synthesis of tertiary N-acyloxymethylamide prodrugs of carboxylic acid drugs. Tetrahedron Lett. 35: 7107-7110 (1994).
    • (1994) Tetrahedron Lett. , vol.35 , pp. 7107-7110
    • Moreira, R.1    Mendes, E.2    Calheiros, T.3    Bacelo, M.J.4    Iley, J.5
  • 12
    • 0001736435 scopus 로고
    • Correlation of solvolysis rates. IV. Solvent effects on enthalpy and entropy of activation for solvolysis of t-butyl chloride
    • S. Winstein and A.H. Fainberg. Correlation of solvolysis rates. IV. Solvent effects on enthalpy and entropy of activation for solvolysis of t-butyl chloride. J. Am. Chem. Soc. 79: 5937-5950 (1957).
    • (1957) J. Am. Chem. Soc. , vol.79 , pp. 5937-5950
    • Winstein, S.1    Fainberg, A.H.2
  • 13
    • 0013557823 scopus 로고
    • Solvent effects in the solvolysis of aryl di-tert-butylcarbinyl p-nitrobenzoates in aqueous acetic acid. Substituent effects on transition state charge separation
    • J.S. Lomas and J.-E. Dubois. Solvent effects in the solvolysis of aryl di-tert-butylcarbinyl p-nitrobenzoates in aqueous acetic acid. Substituent effects on transition state charge separation. J. Org. Chem. 40: 3303-3305 (1975)
    • (1975) J. Org. Chem. , vol.40 , pp. 3303-3305
    • Lomas, J.S.1    Dubois, J.-E.2
  • 14
    • 0023894603 scopus 로고
    • Potential improvement in the shelf life of parenterals using the prodrug approach: Bacampicillin and talampicillin hydrolysis kinetics and utilization time
    • N.-A.T. Nguyen, L.M. Mortada, and R.E. Notari. Potential improvement in the shelf life of parenterals using the prodrug approach: bacampicillin and talampicillin hydrolysis kinetics and utilization time. Pharm. Res. 5: 288-296 (1988).
    • (1988) Pharm. Res. , vol.5 , pp. 288-296
    • Nguyen, N.-A.T.1    Mortada, L.M.2    Notari, R.E.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.