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Volumn 54, Issue 17, 1998, Pages 4223-4242

A general method for the synthesis of O-alkyl N,O'-arylphosphoramidates and its application to the synthesis of a transition state analogue for carbamate hydrolysis

Author keywords

[No Author keywords available]

Indexed keywords

CARBAMIC ACID; DRUG CARRIER; PHOSPHORAMIDIC ACID DERIVATIVE; PRODRUG; TUMOR ANTIGEN;

EID: 0032560152     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00123-9     Document Type: Article
Times cited : (5)

References (42)
  • 1
    • 0345678344 scopus 로고    scopus 로고
    • 1. The ADAPT approach is an extension of ADEPT (antibody-directed enzyme prodrug therapy) in which non-human enzymes are used instead of catalytic antibodies. However, these enzymes are highly immunogenic in humans. Thus, the focus on human catalytic antibodies. For recent reviews of ADEPT see: Jungheim, L. N.; Sheperd, T. A. Chem. Rev. 1994, 94, 1553 and Adv. Drug Del. Rev. 1996, 22, No.3., K. Bagshawe Ed.
    • (1994) Chem. Rev. , vol.94 , pp. 1553
    • Jungheim, L.N.1    Sheperd, T.A.2
  • 2
    • 0345678344 scopus 로고    scopus 로고
    • K. Bagshawe Ed.
    • 1. The ADAPT approach is an extension of ADEPT (antibody-directed enzyme prodrug therapy) in which non-human enzymes are used instead of catalytic antibodies. However, these enzymes are highly immunogenic in humans. Thus, the focus on human catalytic antibodies. For recent reviews of ADEPT see: Jungheim, L. N.; Sheperd, T. A. Chem. Rev. 1994, 94, 1553 and Adv. Drug Del. Rev. 1996, 22, No.3., K. Bagshawe Ed.
    • (1996) Adv. Drug Del. Rev. , vol.22 , Issue.3
  • 4
    • 0010639598 scopus 로고    scopus 로고
    • note
    • 3. The reaction catalyzed by the antibody must not be catalyzed by human enzymes in order to avoid premature formation of the drug.
  • 7
    • 0024098393 scopus 로고
    • 5. Lerner, R. A.; Benkovic, S. J. BioEssays 1988, 9, 107. See also: Lerner, R. A., Hosp. Prac. 1993, 53.
    • (1993) Hosp. Prac. , pp. 53
    • Lerner, R.A.1
  • 10
    • 0010728254 scopus 로고    scopus 로고
    • note
    • 8. Carbamates are stable relatively stable to hydrolysis by most proteases and esterases and have therefore been used extensively as prodrugs and enzyme inhibitors. See references 9 and 1.
  • 13
    • 0019453510 scopus 로고
    • (b) The prodrug system described in Scheme 1 is very similar to the self-immolative prodrug linkage developed by Katzenellenbogen and coworkers. See: Carl, P. L.; Chakravarty, P. K.; Katzenellenbogen, J. A. J. Med. Chem. 1981, 24, 479.
    • (1981) J. Med. Chem. , vol.24 , pp. 479
    • Carl, P.L.1    Chakravarty, P.K.2    Katzenellenbogen, J.A.3
  • 18
    • 0003607090 scopus 로고
    • New York, Wiley Interscience Chp 16
    • 14. For an overview of methods for synthesizing this class of compounds see: Kosalopoff, G. M.; Maier, L. "Organic Phosphorus Compounds" New York, Wiley Interscience 1972. Chp 16.
    • (1972) Organic Phosphorus Compounds
    • Kosalopoff, G.M.1    Maier, L.2
  • 19
    • 0010685242 scopus 로고    scopus 로고
    • note
    • 15. These reagents are prepared using phosphorous oxychloride. By purifying the initial O-phenylphosphoric dichloride or N-phenylphosphoramidic dichloride derivative (rather than reacting the aniline, phenolic and alcohol derivatives consecutively with phosphorus oxychloride) subsequent reactions proceed much cleaner and complex mixtures of products are, to a certain extent, avoided. Alkyldichlorophosphates, such as methyldichlorophosphate, are not commonly used as starting materials due to loss of the alkyl group during the synthesis.
  • 26
    • 0010642198 scopus 로고    scopus 로고
    • note
    • 2 but lower yields were obtained.
  • 30
    • 0010680995 scopus 로고    scopus 로고
    • note
    • 26. We had initially avoided this protecting group since we were concerned of the possibility that the nucleophile required for its removal would also cause loss of the benzyl protecting group from the phosphate.
  • 32
    • 0024982305 scopus 로고
    • 28. Competition experiments with various activated esters of N-protected amino acids have shown that the Pfp esters are more reactive than the NHS esters for peptide bond formation. See: Hudson, D. Peptide Res. 1990, 3, 51.
    • (1990) Peptide Res. , vol.3 , pp. 51
    • Hudson, D.1
  • 34
    • 85004826932 scopus 로고
    • 30. DCC is the coupling agent most commonly employed for forming Pfp esters. See: Kisfaludy, L.; Schon, I. Synthesis, 1983, 325.
    • (1983) Synthesis , pp. 325
    • Kisfaludy, L.1    Schon, I.2
  • 35
    • 0010641041 scopus 로고    scopus 로고
    • note
    • 31. Antibody screening and production is being performed by Prof. William Crosby at the Plant Biotechnology Institute, Saskatoon, Canada. For a description of the phage display library see reference 32.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.