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Volumn , Issue 18, 2007, Pages 3003-3011

A quantitative investigation of the water-solubilizing properties of branched oligoglycerols

Author keywords

Glycerols; Hydroxylation; Iminodiacetic acid; Oligomers; Solvolysis

Indexed keywords


EID: 34347334687     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200601036     Document Type: Article
Times cited : (15)

References (37)
  • 11
    • 34347328952 scopus 로고    scopus 로고
    • C. G. Wermuth, J. de La Fontaine, Practice of Medicinal Chemistry, 2nd ed., Elsevier, Amsterdam, Boston, Heidelberg, London, New York, Oxford, Paris, San Diego, San Francisco, Singapore, Sydney, Tokyo, 2003, pp. 617-630.
    • C. G. Wermuth, J. de La Fontaine, Practice of Medicinal Chemistry, 2nd ed., Elsevier, Amsterdam, Boston, Heidelberg, London, New York, Oxford, Paris, San Diego, San Francisco, Singapore, Sydney, Tokyo, 2003, pp. 617-630.
  • 12
    • 0015211527 scopus 로고    scopus 로고
    • Isolation: M. C. Wani, H. L. Talyor, M. E. Wall, P. Coggon, A. T. McPhail, J. Am. Chem. Soc. 1971, 93, 2325-2326;
    • a) Isolation: M. C. Wani, H. L. Talyor, M. E. Wall, P. Coggon, A. T. McPhail, J. Am. Chem. Soc. 1971, 93, 2325-2326;
  • 13
    • 0025333168 scopus 로고    scopus 로고
    • anticancer activity: E. K. Rowinsky, L. A. Cazenave, R. C. Donehower, J. Natl. Cancer Inst. 1990, 82, 1247-1259;
    • b) anticancer activity: E. K. Rowinsky, L. A. Cazenave, R. C. Donehower, J. Natl. Cancer Inst. 1990, 82, 1247-1259;
  • 14
    • 84994521433 scopus 로고    scopus 로고
    • anti-cancer activity: E. K. Rowensky, R. C. Donehower, N. Engl. J. Med. 1995, 332, 1004-1014;
    • c) anti-cancer activity: E. K. Rowensky, R. C. Donehower, N. Engl. J. Med. 1995, 332, 1004-1014;
  • 15
    • 0027273772 scopus 로고    scopus 로고
    • water solubility: D. M. Vyas, H. Wong, A. R. Crosswell, A. M. Casazza, J. O. Mamber, S. W. Doyle, T. W. Knipe, Bioorg. Med. Chem. Lett. 1993, 3, 1357-1360.
    • d) water solubility: D. M. Vyas, H. Wong, A. R. Crosswell, A. M. Casazza, J. O. Mamber, S. W. Doyle, T. W. Knipe, Bioorg. Med. Chem. Lett. 1993, 3, 1357-1360.
  • 19
    • 0035117488 scopus 로고    scopus 로고
    • Synthesis of various other oligomers of glycerol have been described: S. Cassel, C. Debaig, T. Benvegnu, P. Chaimbault, M. Lafosse, D. Plusquellec, P. Rollin, Eur. J. Org. Chem. 2001, 875-896.
    • Synthesis of various other oligomers of glycerol have been described: S. Cassel, C. Debaig, T. Benvegnu, P. Chaimbault, M. Lafosse, D. Plusquellec, P. Rollin, Eur. J. Org. Chem. 2001, 875-896.
  • 20
    • 0032539244 scopus 로고    scopus 로고
    • Although no evaluation of water solubilization has been performed, the synthesis of dendrimers consisting of symmetrically linked glycerols or serinols assembled via linkers has been demonstrated: a M. Jayaraman, J. M. J. Fréchet, J. Am. Chem. Soc. 1998, 120, 12996-12997;
    • Although no evaluation of water solubilization has been performed, the synthesis of dendrimers consisting of symmetrically linked glycerols or serinols assembled via linkers has been demonstrated: a) M. Jayaraman, J. M. J. Fréchet, J. Am. Chem. Soc. 1998, 120, 12996-12997;
  • 29
    • 33745945620 scopus 로고    scopus 로고
    • For the preparation of p-boronophenylalanine, see: M. F. Hawthorn, Angew. Chem. Int. Ed. Engl. 1993, 32, 950-984.
    • For the preparation of p-boronophenylalanine, see: M. F. Hawthorn, Angew. Chem. Int. Ed. Engl. 1993, 32, 950-984.
  • 33
    • 34347332122 scopus 로고    scopus 로고
    • Linear-type oligo- and polyglycerols have a number of uncontrolled asymmetric centers.[7
    • [7]
  • 34
    • 33646716870 scopus 로고    scopus 로고
    • The use of an octaarginine moiety for both water solubility and membrane permeation has been reported: L. R. Jones, E. A. Goun, R. Shinde, J. B. Rothbard, C. H. Contag, P. A. Wender, J. Am. Chem. Soc. 2006, 128, 6526-6527
    • The use of an octaarginine moiety for both water solubility and membrane permeation has been reported: L. R. Jones, E. A. Goun, R. Shinde, J. B. Rothbard, C. H. Contag, P. A. Wender, J. Am. Chem. Soc. 2006, 128, 6526-6527.
  • 35
    • 34347348857 scopus 로고    scopus 로고
    • When compounds more polar than 8 were modified with various BGL-modified agents, a saturated aqueous solution of the corresponding tetraol or octaol derivatives could not be prepared (too water-soluble). When compounds less polar than 8 were modified similarly, the water solubility of the corresponding monool or diol derivatives could not reproducibly be measured. This is the reason why 8 was chosen.
    • When compounds more polar than 8 were modified with various BGL-modified agents, a saturated aqueous solution of the corresponding tetraol or octaol derivatives could not be prepared (too water-soluble). When compounds less polar than 8 were modified similarly, the water solubility of the corresponding monool or diol derivatives could not reproducibly be measured. This is the reason why 8 was chosen.
  • 37
    • 34347360501 scopus 로고    scopus 로고
    • Although the preparation of an octabenzyl ether consisting of seven glycerol units has been attempted, we have yet to succeed in its synthesis. Therefore octabenzyl ether 14a′, which consists of six glycerol units and one iminodiacetic acid unit, was synthesized instead, Chemical Equation Presented
    • Although the preparation of an octabenzyl ether consisting of seven glycerol units has been attempted, we have yet to succeed in its synthesis. Therefore octabenzyl ether 14a′, which consists of six glycerol units and one iminodiacetic acid unit, was synthesized instead. (Chemical Equation Presented)


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.