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Volumn 51, Issue 14, 2008, Pages 4331-4339

Discovery of phosphonic diamide prodrugs and their use for the oral delivery of a series of fructose 1,6-bisphosphatase inhibitors

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; AMINO ACID DERIVATIVE; DIAMIDE; FRUCTOSE 1,6 BISPHOSPHATASE INHIBITOR; FRUCTOSE BISPHOSPHATASE; GLUCOSE; MB 05032; MB 06322; PHOSPHONIC ACID DERIVATIVE; PRODRUG; THIAZOLE DERIVATIVE;

EID: 47749099269     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm8001235     Document Type: Article
Times cited : (51)

References (27)
  • 2
    • 37849027557 scopus 로고    scopus 로고
    • Structure-guided design of AMP mimics that inhibit fructose 1,6-bisphosphatase with high affinity and specificity
    • Erion, M. D.; Dang, Q.; Reddy, M. R.; Kasibhatla, S. R.; Huang, J.; Lipscomb, W. N.; van Poelje, P. D. Structure-guided design of AMP mimics that inhibit fructose 1,6-bisphosphatase with high affinity and specificity. J. Am. Chem. Soc. 2007, 129, 15480-15490.
    • (2007) J. Am. Chem. Soc , vol.129 , pp. 15480-15490
    • Erion, M.D.1    Dang, Q.2    Reddy, M.R.3    Kasibhatla, S.R.4    Huang, J.5    Lipscomb, W.N.6    van Poelje, P.D.7
  • 3
    • 37849024068 scopus 로고    scopus 로고
    • Discovery of potent and specific fructose-1,6-bisphosphatase inhibitors and a series of orally-bioavailable phosphoramidase-sensitive prodrugs for the treatment of type 2 diabetes
    • Dang, Q.; Kasibhatla, S. R.; Reddy, K. R.; Jiang, T.; Reddy, M. R.; Potter, S. C.; Fujitaki, J. M.; van Poelje, P. D.; Huang, J.; Lipscomb, W. N.; Erion, M. D. Discovery of potent and specific fructose-1,6-bisphosphatase inhibitors and a series of orally-bioavailable phosphoramidase-sensitive prodrugs for the treatment of type 2 diabetes. J. Am. Chem. Soc. 2007, 129, 15491-15502.
    • (2007) J. Am. Chem. Soc , vol.129 , pp. 15491-15502
    • Dang, Q.1    Kasibhatla, S.R.2    Reddy, K.R.3    Jiang, T.4    Reddy, M.R.5    Potter, S.C.6    Fujitaki, J.M.7    van Poelje, P.D.8    Huang, J.9    Lipscomb, W.N.10    Erion, M.D.11
  • 4
    • 33644895702 scopus 로고    scopus 로고
    • Organophosphonic acids as drug candidates
    • Dang, Q. Organophosphonic acids as drug candidates. Expert Opin. Ther. Pat. 2006, 16, 343-348.
    • (2006) Expert Opin. Ther. Pat , vol.16 , pp. 343-348
    • Dang, Q.1
  • 5
    • 0343844454 scopus 로고    scopus 로고
    • Prodrugs of phosphates, phosphonates, and phosphinates
    • Krise, J. P.; Stella, V. J. Prodrugs of phosphates, phosphonates, and phosphinates. Adv. Drug Delivery Rev. 1996, 19, 287-310.
    • (1996) Adv. Drug Delivery Rev , vol.19 , pp. 287-310
    • Krise, J.P.1    Stella, V.J.2
  • 6
    • 43049112098 scopus 로고    scopus 로고
    • Prodrugs of phosphates and phosphonates
    • Hecker, S. J.; Erion, M. D. Prodrugs of phosphates and phosphonates. J. Med. Chem. 2008, 51, 2328-2345.
    • (2008) J. Med. Chem , vol.51 , pp. 2328-2345
    • Hecker, S.J.1    Erion, M.D.2
  • 8
    • 37049067781 scopus 로고
    • Prodrugs of phosphonoformate: The effect of para-substituents on the products, kinetics and mechanims of hydrolysis of dibenzyl methoxycarbonylphosphonate
    • Mitchell, A. G.; Thompson, W.; Nicholls, D.; Irwin, W. J.; Freeman, S. Prodrugs of phosphonoformate: the effect of para-substituents on the products, kinetics and mechanims of hydrolysis of dibenzyl methoxycarbonylphosphonate. J Chem. Soc., Perkin Trans. 2 1992, 1145.
    • (1992) J Chem. Soc., Perkin Trans. 2 , pp. 1145
    • Mitchell, A.G.1    Thompson, W.2    Nicholls, D.3    Irwin, W.J.4    Freeman, S.5
  • 10
    • 0028819889 scopus 로고
    • Mononucleoside phosphotriester derivatives with S-acyl-2-thioethyl bioreversible phosphate-protecting groups: Intracellular delivery of 3′-azido-2′,3′- dideoxythymidine 5′-monophosphate
    • Lefebvre, I.; Perigaud, C.; Pompon, A.; Aubertin, A. M.; Girardet, J. L.; Kirn, A.; Gosselin, G.; Imbach, J. L. Mononucleoside phosphotriester derivatives with S-acyl-2-thioethyl bioreversible phosphate-protecting groups: intracellular delivery of 3′-azido-2′,3′- dideoxythymidine 5′-monophosphate. J. Med. Chem. 1995, 38, 3941-3950.
    • (1995) J. Med. Chem , vol.38 , pp. 3941-3950
    • Lefebvre, I.1    Perigaud, C.2    Pompon, A.3    Aubertin, A.M.4    Girardet, J.L.5    Kirn, A.6    Gosselin, G.7    Imbach, J.L.8
  • 11
    • 0026561408 scopus 로고
    • Aryl phosphate derivatives of AZT retain activity against HIV1 in cell lines which are resistant to the action of AZT
    • McGuigan, C.; Pathirana, R. N.; Mahmood, N.; Devine, K. G.; Hay, A. J. Aryl phosphate derivatives of AZT retain activity against HIV1 in cell lines which are resistant to the action of AZT. Antiviral Res. 1992, 17, 311-321.
    • (1992) Antiviral Res , vol.17 , pp. 311-321
    • McGuigan, C.1    Pathirana, R.N.2    Mahmood, N.3    Devine, K.G.4    Hay, A.J.5
  • 12
    • 0026646563 scopus 로고
    • Phosphate derivatives of AZT display enhanced selectivity of action against HIV 1 by comparison to the parent nucleoside
    • McGuigan, C.; Nickson, C.; Petrik, J.; Karpas, A. Phosphate derivatives of AZT display enhanced selectivity of action against HIV 1 by comparison to the parent nucleoside. FEBS Lett. 1992, 310, 171-174.
    • (1992) FEBS Lett , vol.310 , pp. 171-174
    • McGuigan, C.1    Nickson, C.2    Petrik, J.3    Karpas, A.4
  • 13
    • 11144357250 scopus 로고    scopus 로고
    • Design, synthesis, and characterization of a series of cytochrome P(450) 3A-activated prodrugs (HepDirect prodrugs) useful for targeting phosph(on)ate-based drugs to the liver
    • Erion, M. D.; Reddy, K. R.; Boyer, S. H.; Matelich, M. C.; Gomez-Galeno, J.; Lemus, R. H.; Ugarkar, B. G.; Colby, T. J.; Schanzer, J.; Van Poelje, P. D. Design, synthesis, and characterization of a series of cytochrome P(450) 3A-activated prodrugs (HepDirect prodrugs) useful for targeting phosph(on)ate-based drugs to the liver. J. Am. Chem. Soc. 2004, 126, 5154-5163.
    • (2004) J. Am. Chem. Soc , vol.126 , pp. 5154-5163
    • Erion, M.D.1    Reddy, K.R.2    Boyer, S.H.3    Matelich, M.C.4    Gomez-Galeno, J.5    Lemus, R.H.6    Ugarkar, B.G.7    Colby, T.J.8    Schanzer, J.9    Van Poelje, P.D.10
  • 14
    • 18244398917 scopus 로고    scopus 로고
    • Selective intracellular activation of a novel prodrug of the human immunodeficiency virus reverse transcriptase inhibitor tenofovir leads to preferential distribution and accumulation in lymphatic tissue
    • Lee, W. A.; He, G. X.; Eisenberg, E.; Cihlar, T.; Swaminathan, S.; Mulato, A.; Cundy, K. C. Selective intracellular activation of a novel prodrug of the human immunodeficiency virus reverse transcriptase inhibitor tenofovir leads to preferential distribution and accumulation in lymphatic tissue. Antimicrob. Agents Chemother. 2005, 49, 1898-1906.
    • (2005) Antimicrob. Agents Chemother , vol.49 , pp. 1898-1906
    • Lee, W.A.1    He, G.X.2    Eisenberg, E.3    Cihlar, T.4    Swaminathan, S.5    Mulato, A.6    Cundy, K.C.7
  • 15
    • 0025856241 scopus 로고
    • Synthesis and anti-HIV activity of some novel phosphoradiamidate derivatives of 3′-azido-3′-deoxythymidine (AZT)
    • Jones, B. C. N. M.; McGuigan, C.; O'Connor, T. J.; Jeffries, D. J.; Kinchington, D. Synthesis and anti-HIV activity of some novel phosphoradiamidate derivatives of 3′-azido-3′-deoxythymidine (AZT). Antivir. Chem. Chemother. 1991, 2, 35-39.
    • (1991) Antivir. Chem. Chemother , vol.2 , pp. 35-39
    • Jones, B.C.N.M.1    McGuigan, C.2    O'Connor, T.J.3    Jeffries, D.J.4    Kinchington, D.5
  • 17
    • 0038312076 scopus 로고    scopus 로고
    • Evaluation of nucleoside phosphonates and their analogs and prodrugs for inhibition of orthopoxvirus replication
    • Keith, K. A.; Hitchcock, M. J.; Lee, W. A.; Holy, A.; Kern, E. R. Evaluation of nucleoside phosphonates and their analogs and prodrugs for inhibition of orthopoxvirus replication. Antimicrob. Agents Chemother. 2003, 47, 2193-2198.
    • (2003) Antimicrob. Agents Chemother , vol.47 , pp. 2193-2198
    • Keith, K.A.1    Hitchcock, M.J.2    Lee, W.A.3    Holy, A.4    Kern, E.R.5
  • 18
    • 7844240566 scopus 로고
    • Phosphorylation of alcohols and phosphates by oxidation-reduction condensation
    • Mukaiyama, T.; Hashimoto, M. Phosphorylation of alcohols and phosphates by oxidation-reduction condensation. Bull. Chem. Soc. Jpn. 1971, 44, 196-199.
    • (1971) Bull. Chem. Soc. Jpn , vol.44 , pp. 196-199
    • Mukaiyama, T.1    Hashimoto, M.2
  • 19
    • 49649156314 scopus 로고
    • Phosphorylation by oxidation-reduction condensation: Preparation and reaction of S-(2-pyridyl)phosphorothioates
    • Mukaiyama, T.; Hashimoto, M. Phosphorylation by oxidation-reduction condensation: preparation and reaction of S-(2-pyridyl)phosphorothioates. Tetrahedron Lett. 1971, 26, 2425-2428.
    • (1971) Tetrahedron Lett , vol.26 , pp. 2425-2428
    • Mukaiyama, T.1    Hashimoto, M.2
  • 21
    • 0031024171 scopus 로고    scopus 로고
    • Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings
    • Lipinski, C. A.; Lombardo, F.; Dominy, B. W.; Feeney, P. J. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv. Drug Delivery Rev. 1997, 23, 3.
    • (1997) Adv. Drug Delivery Rev , vol.23 , pp. 3
    • Lipinski, C.A.1    Lombardo, F.2    Dominy, B.W.3    Feeney, P.J.4
  • 22
    • 0038071648 scopus 로고    scopus 로고
    • Predicting oral absorption and bioavailability
    • van de Waterbeemd, H.; Jones, B. C. Predicting oral absorption and bioavailability. Prog. Med. Chem. 2003, 41, 1-59.
    • (2003) Prog. Med. Chem , vol.41 , pp. 1-59
    • van de Waterbeemd, H.1    Jones, B.C.2
  • 23
    • 28044461993 scopus 로고    scopus 로고
    • Gomez-Orellana, I. Strategies to improve oral drug bioavailability. Expert Opin. Drug Delivery 2005, 2, 419-433.
    • Gomez-Orellana, I. Strategies to improve oral drug bioavailability. Expert Opin. Drug Delivery 2005, 2, 419-433.
  • 25
    • 0037030653 scopus 로고    scopus 로고
    • Molecular properties that influence the oral bioavailability of drug candidates
    • Veber, D. F.; Johnson, S. R.; Cheng, H. Y.; Smith, B. R.; Ward, K. W.; Kopple, K. D. Molecular properties that influence the oral bioavailability of drug candidates. J. Med. Chem. 2002, 45, 2615-2623.
    • (2002) J. Med. Chem , vol.45 , pp. 2615-2623
    • Veber, D.F.1    Johnson, S.R.2    Cheng, H.Y.3    Smith, B.R.4    Ward, K.W.5    Kopple, K.D.6
  • 27
    • 47749130145 scopus 로고    scopus 로고
    • Unpublished results
    • Unpublished results.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.