메뉴 건너뛰기




Volumn 104, Issue 4, 2015, Pages 1399-1408

Interaction of Model Aryl- and Alkyl-Boronic Acids and 1,2-Diols in Aqueous Solution

Author keywords

1,2 diols,; acid base equilibria; boronic acid; esters; isothermal calorimetry; mannitol; stability; structure property relationship (SPR)

Indexed keywords

1,2 DIOL DERIVATIVE; ALKYL GROUP; AROMATIC COMPOUND; ARYL BORONIC ACID; BORON; BORONIC ACID DERIVATIVE; ESTER; ESTER DERIVATIVE; LEWIS ACID; MANNITOL; POLYOL; SORBITOL; UNCLASSIFIED DRUG; ALCOHOL DERIVATIVE; SOLUTION AND SOLUBILITY;

EID: 84924803322     PISSN: 00223549     EISSN: 15206017     Source Type: Journal    
DOI: 10.1002/jps.24346     Document Type: Article
Times cited : (23)

References (23)
  • 3
    • 84924793277 scopus 로고    scopus 로고
    • Formulation of boronic acid compounds
    • Patent US
    • Plamondon L, Grenier L, Adams J, Gupta S. 2006. Formulation of boronic acid compounds. Patent US 7109323 B2.
    • (2006)
    • Plamondon, L.1    Grenier, L.2    Adams, J.3    Gupta, S.4
  • 4
    • 84924793276 scopus 로고    scopus 로고
    • Formulation of boronic acid compounds
    • Patent US
    • Gupta SL, Stella VJ, Waugh W. 2005. Formulation of boronic acid compounds. Patent US6958319.
    • (2005)
    • Gupta, S.L.1    Stella, V.J.2    Waugh, W.3
  • 5
    • 84924793276 scopus 로고    scopus 로고
    • Formulation of boronic acid compounds
    • Patent US
    • Gupta SL, Stella VJ, Waugh W. 2005. Formulation of boronic acid compounds. Patent US6713446 B2.
    • (2005)
    • Gupta, S.L.1    Stella, V.J.2    Waugh, W.3
  • 6
    • 0033817605 scopus 로고    scopus 로고
    • Degradation pathways of a peptide boronic acid derivative, 2-Pyz-(CO)-Phe-Leu-B (OH) 2
    • Wu S, Waugh W, Stella VJ. 2000. Degradation pathways of a peptide boronic acid derivative, 2-Pyz-(CO)-Phe-Leu-B (OH) 2. J Pharm Sci 89:758-765.
    • (2000) J Pharm Sci , vol.89 , pp. 758-765
    • Wu, S.1    Waugh, W.2    Stella, V.J.3
  • 7
    • 85027926604 scopus 로고    scopus 로고
    • Analysis of two commercially available bortezomib products: Differences in assay active agent and impurity profile
    • Byrn SR, Tishmack PA, Milton MJ, van de Velde H. 2011. Analysis of two commercially available bortezomib products: Differences in assay active agent and impurity profile. AAPS Pharm Sci Tech 12:461-467.
    • (2011) AAPS Pharm Sci Tech , vol.12 , pp. 461-467
    • Byrn, S.R.1    Tishmack, P.A.2    Milton, M.J.3    Van De Velde, H.4
  • 9
    • 0037405256 scopus 로고    scopus 로고
    • Boronic acid compounds as potential pharmaceutical agents
    • Yang W, Gao X, Wang B. 2003. Boronic acid compounds as potential pharmaceutical agents. Med Res Rev 23:346-368.
    • (2003) Med Res Rev , vol.23 , pp. 346-368
    • Yang, W.1    Gao, X.2    Wang, B.3
  • 10
    • 7044263179 scopus 로고    scopus 로고
    • The relationship among pKa, pH, and binding constants in the interactions between boronic acids and diols - It is not as simple as it appears
    • Yan J, Springsteen G, Deeter S, Wang B. 2004. The relationship among pKa, pH, and binding constants in the interactions between boronic acids and diols - It is not as simple as it appears. Tetrahedron 60:11205-11209.
    • (2004) Tetrahedron , vol.60 , pp. 11205-11209
    • Yan, J.1    Springsteen, G.2    Deeter, S.3    Wang, B.4
  • 11
    • 0037167074 scopus 로고    scopus 로고
    • A detailed examination of boronic acid-diol complexation
    • Springsteen G, Wang B. 2002. A detailed examination of boronic acid-diol complexation. Tetrahedron 58:5291-5300.
    • (2002) Tetrahedron , vol.58 , pp. 5291-5300
    • Springsteen, G.1    Wang, B.2
  • 14
    • 0037353766 scopus 로고    scopus 로고
    • 11B NMR study of p-carboxybenzeneboronic acid ions for complex formation with some monosaccharides
    • Islam TM, Yoshino K, Sasane, A. 2003. 11B NMR study of p-carboxybenzeneboronic acid ions for complex formation with some monosaccharides. Anal Sci 19:455-460.
    • (2003) Anal Sci , vol.19 , pp. 455-460
    • Islam, T.M.1    Yoshino, K.2    Sasane, A.3
  • 15
    • 82255179375 scopus 로고    scopus 로고
    • Physicochemical investigation of the influence of saccharide-based parenteral formulation excipients on L-p-boronphenylalanine solubilisation for boron neutron capture therapy
    • Schmidt E, Dooley N, Ford SJ, Elliott M, Halbert GW. 2012. Physicochemical investigation of the influence of saccharide-based parenteral formulation excipients on L-p-boronphenylalanine solubilisation for boron neutron capture therapy. J Pharm Sci 101:223-232.
    • (2012) J Pharm Sci , vol.101 , pp. 223-232
    • Schmidt, E.1    Dooley, N.2    Ford, S.J.3    Elliott, M.4    Halbert, G.W.5
  • 16
    • 33846610054 scopus 로고    scopus 로고
    • Which is reactive in alkaline solution, boronate ion or boronic acid? Kinetic evidence for reactive trigonal boronic acid in an alkaline solution
    • Iwatsuki S, Nakajima S, Inamo M, Takagi HD, Ishihara K. 2007. Which is reactive in alkaline solution, boronate ion or boronic acid? Kinetic evidence for reactive trigonal boronic acid in an alkaline solution. Inorg Chem 46:354-356.
    • (2007) Inorg Chem , vol.46 , pp. 354-356
    • Iwatsuki, S.1    Nakajima, S.2    Inamo, M.3    Takagi, H.D.4    Ishihara, K.5
  • 17
    • 0001481414 scopus 로고
    • Cyclic benzeneboronate esters
    • Sugihara JM, Bowman CM. 1958. Cyclic benzeneboronate esters. J Am Chem Soc 80:2443-2446.
    • (1958) J Am Chem Soc , vol.80 , pp. 2443-2446
    • Sugihara, J.M.1    Bowman, C.M.2
  • 18
    • 33847805652 scopus 로고
    • Cyclic phenylboronates as hydroxyl protecting groups in the synthesis of monoesters of macrolide aglycones
    • Perun TJ, Martin JR, Egan RS. 1974. Cyclic phenylboronates as hydroxyl protecting groups in the synthesis of monoesters of macrolide aglycones. J Org Chem 39:1490-1493.
    • (1974) J Org Chem , vol.39 , pp. 1490-1493
    • Perun, T.J.1    Martin, J.R.2    Egan, R.S.3
  • 19
    • 0001567673 scopus 로고
    • Intramolecular-catalyzed sulfonamide hydrolysis. VII. The Thorpe- Ingold effect in the intramolecular carboxyl-catalyzed hydrolysis of sulfonamides
    • Jager J, Graafland T, Schenk H, Kirby AJ, Engberts JBFN. 1984. Intramolecular-catalyzed sulfonamide hydrolysis. VII. The Thorpe- Ingold effect in the intramolecular carboxyl-catalyzed hydrolysis of sulfonamides. J Amer Chem Soc 106:139-143.
    • (1984) J Amer Chem Soc , vol.106 , pp. 139-143
    • Jager, J.1    Graafland, T.2    Schenk, H.3    Kirby, A.J.4    Engberts, J.B.F.N.5
  • 20
    • 37049084865 scopus 로고
    • Reactions of dithiane derived alcohols: Promotion of the Thorpe-Ingold effect by trimethylsilyl and tert-butyl substituents
    • Davey AE, Parsons AF, Taylor RJK. 1989. Reactions of dithiane derived alcohols: Promotion of the Thorpe-Ingold effect by trimethylsilyl and tert-butyl substituents. J Chem Soc Perkin Trans I 10:1853-1858.
    • (1989) J Chem Soc Perkin Trans I , vol.10 , pp. 1853-1858
    • Davey, A.E.1    Parsons, A.F.2    Taylor, R.J.K.3
  • 21
    • 0025779252 scopus 로고
    • The Thorpe-Ingold effect in the synthesis of tetrahydro-furans and pyrans by competitive cyclization with phenylthio migration
    • McIntyre S, Sansbury FH, Warren S. 1991. The Thorpe-Ingold effect in the synthesis of tetrahydro-furans and pyrans by competitive cyclization with phenylthio migration. Tetra Let 32:5409-5412.
    • (1991) Tetra Let , vol.32 , pp. 5409-5412
    • McIntyre, S.1    Sansbury, F.H.2    Warren, S.3
  • 23
    • 0000666574 scopus 로고
    • Boron-11 NMR study of the complex formation of borate with catechol and L-dopa
    • Yoshino K, Kotaka M, Okamoto M, Kakihana H. 1979. Boron-11 NMR study of the complex formation of borate with catechol and L-dopa. Bull Chem Soc Japan 52:3005-3009.
    • (1979) Bull Chem Soc Japan , vol.52 , pp. 3005-3009
    • Yoshino, K.1    Kotaka, M.2    Okamoto, M.3    Kakihana, H.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.