메뉴 건너뛰기




Volumn 49, Issue 11, 2006, Pages 3368-3376

Design and synthesis of phosphotyrosine peptidomimetic prodrugs

Author keywords

[No Author keywords available]

Indexed keywords

N METHYL N (4 CHLOROBUTYL) O (5 NITROFURYL 2 METHYL) O (4 (1 (3 CARBAMOYL 4 CYCLOHEXYLMETHOXYPHENYL)ETHYLCARBAMOYL)) PHENYL PHOSPHORODIAMIDATE; N METHYL N (4 CHLOROBUTYL) O (5 NITROFURYL 2 METHYL) O [1 (3 CARBAMOYL 4 CYCLOHEXYLMETHOXYPHENYL)METHYL]PHENYL PHOSPHORAMIDATE; N METHYL N (4 CHLOROBUTYL) O (5 NITROFURYL 2 METHYL) O [4 [1 (3 CARBAMOYL 4 CYCLOHEXYLMETHOXYPHENYL)ETHYLCARBAMOYL]]PHENYL PHOSPHORAMIDATE; N METHYL N (4 CHLOROBUTYL) O (5 NITROFURYL 2 METHYL) O [4 [1 (3 CARBAMOYL 4 CYCLOHEXYLMETHOXYPHENYL)ETHYLCARBAMOYL]METHYL]PHENYL PHOSPHORODIAMIDATE; N METHYL N (4 CHLOROBUTYL) O (5 NITROFURYL 2 METHYL) O [4 [2 [ACETYLAMINO 2 [1 (3 CARBAMOYL 4 CYCLOHEXYLMETHOXYPHENYL)ETHYLCARBAMOYL]ETHYL]]]PHENYL PHOSPHORODIAMIDATE; N METHYL N (4 CHLOROBUTYL) O (5 NITROFURYL 2 METHYL) O [4 [2 ACETYLAMINO 2 [1 (3 CARBAMOYL 4 CYCLOHEXYLMETHOXYPHENYL)ETHYLCARBAMOYL]ETHYL]]PHENYL PHOSPHORAMIDATE; PEPTIDOMIMETIC; PHOSPHATE; PHOSPHORODIAMIDATE DERIVATIVE; PHOSPHOTYROSINE; PRODRUG; PROTEIN SH2; UNCLASSIFIED DRUG;

EID: 33744786265     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm060142p     Document Type: Article
Times cited : (31)

References (31)
  • 1
    • 0025765803 scopus 로고
    • SH2 and SH3 domains: Elements that control interactions of cytoplasmic signaling proteins
    • Koch, C. A.; Anderson, D.; Moran, M. F.; Ellis, C.; Pawson, T. SH2 and SH3 Domains: Elements that Control Interactions of Cytoplasmic Signaling Proteins. Science 1991, 252, 668-74.
    • (1991) Science , vol.252 , pp. 668-674
    • Koch, C.A.1    Anderson, D.2    Moran, M.F.3    Ellis, C.4    Pawson, T.5
  • 2
    • 0029880630 scopus 로고    scopus 로고
    • SH2 Domain protein interaction and possibilities for pharmacological intervention
    • Beattie, J. SH2 Domain Protein Interaction and Possibilities for Pharmacological Intervention. Cell. Signalling 1996, 8, 75-86.
    • (1996) Cell. Signalling , vol.8 , pp. 75-86
    • Beattie, J.1
  • 7
    • 0026674221 scopus 로고
    • Characterization of protein tyrosine kinases from human breast cancer: Involvement of the c-src oncogene product
    • Ottenhoff-Kalff, A. E.; Rijsken, G.; van Beurden, E. A. C. M.; Hennipman, A.; Michles, A. A.; Staal, G. E. J. Characterization of protein tyrosine kinases from human breast cancer: involvement of the c-src oncogene product. Cancer Res. 1992, 52, 4773-8.
    • (1992) Cancer Res. , vol.52 , pp. 4773-4778
    • Ottenhoff-Kalff, A.E.1    Rijsken, G.2    Van Beurden, E.A.C.M.3    Hennipman, A.4    Michles, A.A.5    Staal, G.E.J.6
  • 8
    • 0031229746 scopus 로고    scopus 로고
    • The Lck SH2 phosphotyrosine binding site is critical for efficient TCR-induced procesive tyrosine phosphorylation of the ζ-chain and IL-2 production
    • Lewis, L. A.; Chung, C. D.; Chen, J. P. J. R.; Moran, M.; Patel, V. P.; Miceli, M. C. The Lck SH2 Phosphotyrosine Binding Site Is Critical for Efficient TCR-Induced Procesive Tyrosine Phosphorylation of the ζ-Chain and IL-2 Production. J. Immunol. 1997, 159, 2292-300.
    • (1997) J. Immunol. , vol.159 , pp. 2292-2300
    • Lewis, L.A.1    Chung, C.D.2    Chen, J.P.J.R.3    Moran, M.4    Patel, V.P.5    Miceli, M.C.6
  • 9
    • 0031796005 scopus 로고    scopus 로고
    • Src homology-2 domains: Structure, mechanisms, and drug discovery
    • Sawyer T. K. Src homology-2 domains: Structure, mechanisms, and drug discovery. Biopolymers 1998, 47, 243-61.
    • (1998) Biopolymers , vol.47 , pp. 243-261
    • Sawyer, T.K.1
  • 10
    • 0001520063 scopus 로고    scopus 로고
    • Nonpeptidic ligands that target the SH2 domain of the lck tyrosine kinase
    • Lee, T.; Lawrence, D. S. Nonpeptidic ligands that target the SH2 domain of the lck tyrosine kinase. J. Med. Chem. 2000, 43, 1173-9.
    • (2000) J. Med. Chem. , vol.43 , pp. 1173-1179
    • Lee, T.1    Lawrence, D.S.2
  • 14
    • 0032491228 scopus 로고    scopus 로고
    • Design and synthesis of a pyridone-based phosphotyrosine mimetic
    • Fu, J.-M.; Castelhano, A. L. Design and Synthesis of a Pyridone-Based Phosphotyrosine Mimetic. Bioorg. Med. Chem. Lett. 1998, 8, 2813-6.
    • (1998) Bioorg. Med. Chem. Lett. , vol.8 , pp. 2813-2816
    • Fu, J.-M.1    Castelhano, A.L.2
  • 15
    • 0032515137 scopus 로고    scopus 로고
    • Phosphopeptide prodrug bearing an S-Acyl-2-thioethyl enzyme-labile phosphate protection
    • Mathe, C.; Periguad, C.; Gosselin, G.; Imbach, J. L. Phosphopeptide Prodrug Bearing an S-Acyl-2-thioethyl Enzyme-Labile Phosphate Protection. J. Org. Chem. 1998, 63, 8547-50.
    • (1998) J. Org. Chem. , vol.63 , pp. 8547-8550
    • Mathe, C.1    Periguad, C.2    Gosselin, G.3    Imbach, J.L.4
  • 16
    • 0034597614 scopus 로고    scopus 로고
    • Synthesis and biological activity of novel 5-fluoro-2′-deoxyuridine phosphoramidate prodrugs
    • Meyers, C. L. F.; Hong, L.; Joswig, C.; Borch, R. F. Synthesis and biological activity of novel 5-fluoro-2′-deoxyuridine phosphoramidate prodrugs. J. Med. Chem. 2000, 43, 4313-8.
    • (2000) J. Med. Chem. , vol.43 , pp. 4313-4318
    • Meyers, C.L.F.1    Hong, L.2    Joswig, C.3    Borch, R.F.4
  • 17
    • 0035818889 scopus 로고    scopus 로고
    • Synthesis and biological studies of novel nucleoside phosphoramidate prodrugs
    • Tobias, S. C.; Borch, R. F. Synthesis and biological studies of novel nucleoside phosphoramidate prodrugs. J. Med. Chem. 2001, 44, 4475-80.
    • (2001) J. Med. Chem. , vol.44 , pp. 4475-4480
    • Tobias, S.C.1    Borch, R.F.2
  • 18
    • 3142752643 scopus 로고    scopus 로고
    • Synthesis and biological evaluation of a cytarabine phosphoramidate prodrug
    • Tobias, S. C.; Borch, R. F. Synthesis and biological evaluation of a cytarabine phosphoramidate prodrug. Mol. Pharm. 2004, 1, 112-6.
    • (2004) Mol. Pharm. , vol.1 , pp. 112-116
    • Tobias, S.C.1    Borch, R.F.2
  • 19
    • 0029076589 scopus 로고
    • Synthesis and biological evaluation of 5-fluoro-2′-deoxyuridine phosphoramidate analogues
    • Fries, K. M.; Joswig, C.; Borch, R. F. Synthesis and biological evaluation of 5-fluoro-2′-deoxyuridine phosphoramidate analogues. J. Med. Chem. 1995, 38, 2672-80.
    • (1995) J. Med. Chem. , vol.38 , pp. 2672-2680
    • Fries, K.M.1    Joswig, C.2    Borch, R.F.3
  • 20
    • 0034597608 scopus 로고    scopus 로고
    • Activation mechanisms of nucleoside phosphoramidate prodrugs
    • Freel Meyers, C. L.; Borch, R. F. Activation mechanisms of nucleoside phosphoramidate prodrugs. J. Med. Chem. 2000, 43, 4319-27.
    • (2000) J. Med. Chem. , vol.43 , pp. 4319-4327
    • Freel Meyers, C.L.1    Borch, R.F.2
  • 21
    • 0031585714 scopus 로고    scopus 로고
    • Structure-based design of a novel series of nonpeptide ligands that bind to the pp60src SH2 domain
    • Lunney, E. A.; Para, K. S.; Rubin, J. R.; Humblet, C.; Fergus, J. H.; Marks, J. S.; Sawyer, T. K. Structure-based design of a novel series of nonpeptide ligands that bind to the pp60src SH2 domain. J. Am. Chem. Soc. 1997, 119, 12471-6.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 12471-12476
    • Lunney, E.A.1    Para, K.S.2    Rubin, J.R.3    Humblet, C.4    Fergus, J.H.5    Marks, J.S.6    Sawyer, T.K.7
  • 22
    • 0035804302 scopus 로고    scopus 로고
    • Synthesis and evaluation of pteroic acid-conjugated nitroheterocyclic phosphoramidates as folate receptor-targeted alkylating agents
    • Steinberg, G.; Borch, R. F. Synthesis and evaluation of pteroic acid-conjugated nitroheterocyclic phosphoramidates as folate receptor-targeted alkylating agents. J. Med. Chem. 2001, 44, 69-73.
    • (2001) J. Med. Chem. , vol.44 , pp. 69-73
    • Steinberg, G.1    Borch, R.F.2
  • 23
    • 0032552206 scopus 로고    scopus 로고
    • Active carbonate resins: Application to the solid-phase synthesis of alcohol, carbamate and cyclic peptides
    • Alsina, J.; Rabanal, F.; Chiva, C.; Giralt, E.; Albericio, F. Active Carbonate Resins: Application to the Solid-Phase Synthesis of Alcohol, Carbamate and Cyclic Peptides. Tetrahedron 1998, 54, 10125-52.
    • (1998) Tetrahedron , vol.54 , pp. 10125-10152
    • Alsina, J.1    Rabanal, F.2    Chiva, C.3    Giralt, E.4    Albericio, F.5
  • 24
    • 0026703858 scopus 로고
    • A general method for the preparation of benzylic α, α-difluorophosphonic acids; non-hydrolyzable mimetics of phosphotyrosine
    • Smyth, M. S.; Ford, H.; Burke, T. R. A General Method for the Preparation of Benzylic α, α-Difluorophosphonic Acids; Non-Hydrolyzable Mimetics of Phosphotyrosine. Tetrahedron Lett. 1992, 33, 4137-40.
    • (1992) Tetrahedron Lett. , vol.33 , pp. 4137-4140
    • Smyth, M.S.1    Ford, H.2    Burke, T.R.3
  • 25
    • 0026793591 scopus 로고
    • Inhibition of SH2 domain/phosphoprotein association by a nonhydrolyzable phosphonopeptide
    • Domchek, S. M.; Auger, K. R.; Chatterjee, S.; Burke, T. R. Jr; Shoelson, S. E. Inhibition of SH2 domain/phosphoprotein association by a nonhydrolyzable phosphonopeptide. Biochemistry 1992, 31, 9865-70.
    • (1992) Biochemistry , vol.31 , pp. 9865-9870
    • Domchek, S.M.1    Auger, K.R.2    Chatterjee, S.3    Burke Jr., T.R.4    Shoelson, S.E.5
  • 28
    • 0028213283 scopus 로고
    • The palladium-catalyzed asymmetric α-Allylation of carbonyl compounds with chiral allyl esters via enamines and imines
    • Hiroi, K.; Abe, J.; Suya, K.; Sato, S.; Koyama, T. The Palladium-Catalyzed Asymmetric α-Allylation of Carbonyl Compounds with Chiral Allyl Esters via Enamines and Imines. J. Org. Chem. 1994, 59, 203-13.
    • (1994) J. Org. Chem. , vol.59 , pp. 203-213
    • Hiroi, K.1    Abe, J.2    Suya, K.3    Sato, S.4    Koyama, T.5
  • 29
    • 0029939787 scopus 로고    scopus 로고
    • SH2 domain function is essential for the role of the Lck tyrosine kinase in T cell receptor signal transduction
    • Straus, D. B.; Chan, A. C.; Patai, B.; Weiss, A. SH2 domain function is essential for the role of the Lck tyrosine kinase in T cell receptor signal transduction. J. Biol. Chem. 1996, 271, 9976-81.
    • (1996) J. Biol. Chem. , vol.271 , pp. 9976-9981
    • Straus, D.B.1    Chan, A.C.2    Patai, B.3    Weiss, A.4
  • 30
    • 0038068134 scopus 로고    scopus 로고
    • Rosmarinic acid inhibits TCR-induced T cell activation and proliferation in an Lck-dependent manner
    • Won, J.; Hur, Y. G.; Hur, E. M.; Park, S. H.; Kang, M. A.; Choi, Y.; Park, C.; Lee, K. H.; Yun, Y. Rosmarinic acid inhibits TCR-induced T cell activation and proliferation in an Lck-dependent manner. Eur. J. Immunol. 2003, 33, 870-9.
    • (2003) Eur. J. Immunol. , vol.33 , pp. 870-879
    • Won, J.1    Hur, Y.G.2    Hur, E.M.3    Park, S.H.4    Kang, M.A.5    Choi, Y.6    Park, C.7    Lee, K.H.8    Yun, Y.9


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.