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Volumn 64, Issue 8, 1999, Pages 2847-2851

Phosphodiester alkylation with a quinone methide

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOPHOSPHATE; QUINONE DERIVATIVE; QUINONE METHIDE; UNCLASSIFIED DRUG;

EID: 0033574623     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9823745     Document Type: Article
Times cited : (36)

References (43)
  • 4
    • 0000480555 scopus 로고
    • Muller, E., Bayer, O., Eds.; Thieme G. Verlag: Stuttgart, Houben-Weyl
    • (c) Grünanger, P. in Methoden der Organisch Chemie; Muller, E., Bayer, O., Eds.; Thieme G. Verlag: Stuttgart, 1979; Houben-Weyl, Vol. VII/3b, pp 395-521.
    • (1979) Methoden der Organisch Chemie , vol.7 , Issue.3 B , pp. 395-521
    • Grünanger, P.1
  • 8
    • 0017397793 scopus 로고
    • (b) Moore, H. W. Science 1977, 197, 527-532.
    • (1977) Science , vol.197 , pp. 527-532
    • Moore, H.W.1
  • 9
    • 0032549593 scopus 로고    scopus 로고
    • Many nucleic acid base alkylation products by o-quinone methide derivatives have been characterized: (a) Ouyang, A.; Skibo, E. B. J. Org. Chem. 1998, 63, 1893-1900.
    • (1998) J. Org. Chem. , vol.63 , pp. 1893-1900
    • Ouyang, A.1    Skibo, E.B.2
  • 17
    • 0030448144 scopus 로고    scopus 로고
    • Examples of compounds proposed to alkylate and/or cleave DNA through quinone methide intermediates include: (a) Zheng, Q.; Rokita, S. E. J. Org. Chem. 1996, 61, 9080-9081.
    • (1996) J. Org. Chem. , vol.61 , pp. 9080-9081
    • Zheng, Q.1    Rokita, S.E.2
  • 24
    • 0028037754 scopus 로고
    • For an example of a p-quinone methide forming analogue of CC-1065 with potential DNA alkylating abilities, see: Boger, D. L.; Nishi, T.; Teegarden, B. R. J. Org. Chem. 1994, 59, 4943-4949.
    • (1994) J. Org. Chem. , vol.59 , pp. 4943-4949
    • Boger, D.L.1    Nishi, T.2    Teegarden, B.R.3
  • 25
    • 0027496965 scopus 로고
    • An elegant aziridinium derivative has been reported to selectively alkylate the DNA phosphodiester backbone: (a) Skibo, E. B.; Schulz, W. G. J. Med. Chem. 1993, 36, 3050-3055.
    • (1993) J. Med. Chem. , vol.36 , pp. 3050-3055
    • Skibo, E.B.1    Schulz, W.G.2
  • 33
    • 0039539674 scopus 로고
    • A few synthetic methods have been developed to convert dialkyl phosphate salts into trialkyl phosphates: (a) Ayukawa, H.; Ohuch, S.; Ishikawa, M.; Hata, T. Chem. Lett. 1995, 81.
    • (1995) Chem. Lett. , pp. 81
    • Ayukawa, H.1    Ohuch, S.2    Ishikawa, M.3    Hata, T.4
  • 40
    • 0345483057 scopus 로고    scopus 로고
    • note
    • Complete characterization of a related trapped product will be reported in due course.
  • 41
    • 0003601534 scopus 로고    scopus 로고
    • Merck &CO: Whitehouse Station, NJ
    • The Merck Index; Budavari, S., Ed.; Merck &CO: Whitehouse Station, NJ, 1996.
    • (1996) The Merck Index
    • Budavari, S.1
  • 42
    • 0002947088 scopus 로고
    • a of the dibenzylphosphoric acid was estimated to be 0.71 in water/chloroform mixture: Courtemanche, P.; Merlin, J.-C. Bull. Soc. Chim. Fr. 1967, 10, 3911-3919.
    • (1967) Bull. Soc. Chim. Fr. , vol.10 , pp. 3911-3919
    • Courtemanche, P.1    Merlin, J.-C.2
  • 43
    • 0344189183 scopus 로고    scopus 로고
    • note
    • The chemical shifts of the benzylic protons of 2 were 4.85 ppm without MsOH, 4.89 ppm with 0.5 equiv of MsOH, 4.93 ppm with 0.8 equiv of MsOH, and 4.96 ppm with 1.0 equiv of MsOH.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.