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Volumn 3, Issue 2, 2006, Pages 161-173

Sulfonyl-containing nucleoside phosphotriesters and phosphoramidates as novel anticancer prodrugs of 5-fluoro-2′-deoxyuridine 5′- monophosphate (FdUMP)

Author keywords

elimination; 5 FU; Nucleotide prodrug; Sulfonyl

Indexed keywords

2' DEOXYURIDIN 5' YL' BIS[2 (4 TOLYLSULFONYL)ETHYL]PHOSPHATE; 5 FLUORO 2' DEOXYURIDIN 5' YL BIS[2 (4 TOLYLSULFONYL) 1 METHYLETHYL]PHOSPHATE; 5 FLUORO 2' DEOXYURIDIN 5' YL BIS[2 (4 TOLYLSULFONYL)ETHYL]PHOSPHATE; ANTINEOPLASTIC AGENT; FLOXURIDINE PHOSPHATE DERIVATIVE; FLUOROURACIL DERIVATIVE; NUCLEOSIDE PHOSPHOTRIESTER; O,O' 2' DEOXYURIDIN 5' YL [2 (4 TOLYLSULFONYL)ETHYL]N,N BIS(2 CHLOROETHYL)PHOSPHORAMIDATE; O,O' 2' DEOXYURIDIN 5' YL [2 (4 TOLYLSULFONYL)ETHYL]PHOSPHORAMIDATE; O,O' 5 FLUORO 2' DEOXYURIDIN 5' YL [2 (4 NITROPHENYLSULFONYL)ETHYL]N,N BIS(2 CHLOROETHYL)PHOSPHORAMIDATE; O,O' 5 FLUORO 2' DEOXYURIDIN 5' YL [2 (4 TOLYLSULFONYL)ETHYL]N,N BIS(2 CHLOROETHYL)PHOSPHORAMIDATE; O,O' 5 FLUORO 2' DEOXYURIDIN 5' YL [2 (4 TOLYLSULFONYL)ETHYL]PHOSPHORAMIDATE; PHOSPHORAMIDIC ACID DERIVATIVE; PRODRUG; THYMIDINE; THYMIDYLATE SYNTHASE; UNCLASSIFIED DRUG;

EID: 33646380859     PISSN: 15438384     EISSN: 15438392     Source Type: Journal    
DOI: 10.1021/mp0500622     Document Type: Article
Times cited : (11)

References (24)
  • 1
    • 0019753942 scopus 로고
    • On the rational development of a new drug: The example of the fluorinated pyrimidines
    • Heidelberger, C. On the Rational Development of a New Drug: the Example of the Fluorinated Pyrimidines. Cancer Treat. Rep. 1981, 65 (Suppl. 3), 3-9.
    • (1981) Cancer Treat. Rep. , vol.65 , Issue.SUPPL. 3 , pp. 3-9
    • Heidelberger, C.1
  • 3
    • 0026050699 scopus 로고
    • Developments of the fluoropyrimidines as inhibitors of thymidylate synthetase: Pharmacologic and clinical aspects
    • Machover, D. Developments of the Fluoropyrimidines as Inhibitors of Thymidylate Synthetase: Pharmacologic and Clinical Aspects. J. Surg. Oncol. Suppl. 1991, 2, 42-50.
    • (1991) J. Surg. Oncol. Suppl. , vol.2 , pp. 42-50
    • Machover, D.1
  • 5
    • 0027943194 scopus 로고
    • Synthesis and antitumor evaluation of bis[(pivaloyloxy)methyl] 2′-deoxy-5-fluorouridine 5′-monophosphate: (FdUMP): A strategy to introduce nucleotides into cells
    • Farquhar, D.; Khan, S.; Srivastva, D. N.; Saunders: P. P. Synthesis and Antitumor Evaluation of Bis[(pivaloyloxy)methyl] 2′-Deoxy-5-fluorouridine 5′-Monophosphate: (FdUMP): A Strategy To Introduce Nucleotides into Cells. J. Med. Chem. 1994, 37, 3902-9.
    • (1994) J. Med. Chem. , vol.37 , pp. 3902-3909
    • Farquhar, D.1    Khan, S.2    Srivastva, D.N.3    Saunders, P.P.4
  • 6
    • 0029014710 scopus 로고
    • 5′-[4-(pivaloyloxy)-1,3,2-dioxaphosphorinan-2-yl] -2'′deoxy-5-fluorouridine: A membrane-permeating prodrug of 5-fluoro-2′-deoxyuridylic acid (FdUMP)
    • Farquhar, D.; Chen, R.; Khan, S. 5′-[4-(Pivaloyloxy)-1,3,2- dioxaphosphorinan-2-yl]-2'′deoxy-5-fluorouridine: A Membrane-Permeating Prodrug of 5-Fluoro-2′-deoxyuridylic Acid (FdUMP). J. Med. Chem. 1995, 38, 488-95.
    • (1995) J. Med. Chem. , vol.38 , pp. 488-495
    • Farquhar, D.1    Chen, R.2    Khan, S.3
  • 7
    • 0034597614 scopus 로고    scopus 로고
    • Synthesis and biological activity of novel 5-fluoro-2′-deoxyuridine phosphoramidate prodrugs
    • Freel Meyers C. L.; 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
    • Freel Meyers, C.L.1    Hong, L.2    Joswig, C.3    Borch, R.F.4
  • 8
    • 0033736202 scopus 로고    scopus 로고
    • Pronucleotides: Toward the in vivo-delivery of antiviral and anticancer nucleotides
    • Wagner, C. R.; Iyer; V. V.; McIntee, E. J. Pronucleotides: toward the in Vivo-Delivery of Antiviral and Anticancer Nucleotides. Med. Res. Rev. 2000, 20, 417-51.
    • (2000) Med. Res. Rev. , vol.20 , pp. 417-451
    • Wagner, C.R.1    Iyer, V.V.2    McIntee, E.J.3
  • 9
    • 3042559633 scopus 로고    scopus 로고
    • Designing a pronucleotide stratagem: Lessons from amino acid phosphoramidates of antieancer and antiviral pyrimidines
    • Drontle, D. P.; Wagner, C. R. Designing a Pronucleotide Stratagem: Lessons from Amino Acid Phosphoramidates of Antieancer and Antiviral Pyrimidines. Mini-Rev. Med. Chem. 2004, 4, 409-19.
    • (2004) Mini-Rev. Med. Chem. , vol.4 , pp. 409-419
    • Drontle, D.P.1    Wagner, C.R.2
  • 11
    • 3142617909 scopus 로고    scopus 로고
    • Sulfonyl-containing aldophosphamide analogues as novel anticancer prodrugs targeted against cyclophosphamide-resistant tumor cell lines
    • Jain, M.; Fan, J.; Baturay, N. Z.; Kwon, C. H. Sulfonyl-containing Aldophosphamide Analogues as Novel Anticancer Prodrugs Targeted Against Cyclophosphamide-Resistant Tumor Cell Lines. J. Med. Chem. 2004, 47, 3843-52.
    • (2004) J. Med. Chem. , vol.47 , pp. 3843-3852
    • Jain, M.1    Fan, J.2    Baturay, N.Z.3    Kwon, C.H.4
  • 12
    • 0029851158 scopus 로고    scopus 로고
    • Synthesis and biological activity of aromatic amino acid phosphoramidates of 5-fluoro-2′-deoxyuridine and 1-β-arabino-furanosylcytosine: Evidence of phosphoramidase activity
    • Abraham, T. W.; Kaiman, T. I.; McIntee, E. J.; Wagner, C. R. Synthesis and Biological Activity of Aromatic Amino Acid Phosphoramidates of 5-Fluoro-2′-deoxyuridine and 1-β-Arabino-furanosylcytosine: Evidence of Phosphoramidase Activity. J. Med, Chem. 1996, 39, 4569-75.
    • (1996) J. Med. Chem. , vol.39 , pp. 4569-4575
    • Abraham, T.W.1    Kaiman, T.I.2    McIntee, E.J.3    Wagner, C.R.4
  • 13
    • 17644385585 scopus 로고    scopus 로고
    • 31P NMR and genetic analysis establish hinT as the only Escherchia coli purine nucleoside phosphoramidase and as essential for growth under high salt conditions
    • 31P NMR and Genetic Analysis Establish hinT as the only Escherchia Coli Purine Nucleoside Phosphoramidase and as Essential for Growth under High Salt Conditions. J. Biol. Chem. 2005, 280, 15356-61.
    • (2005) J. Biol. Chem. , vol.280 , pp. 15356-15361
    • Chou, T.F.1    Bieganowski, P.2    Shilinski, K.3    Cheng, J.4    Brenner, C.5    Wagner, C.R.6
  • 14
    • 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
  • 15
    • 0022096520 scopus 로고
    • Chemical synthesis of natural and modified oligodeoxynucleotides
    • Nguyen, T. T.; Ulysse, A. Chemical Synthesis of Natural and Modified Oligodeoxynucleotides. Biochimie 1985, 67, 673-84.
    • (1985) Biochimie , vol.67 , pp. 673-684
    • Nguyen, T.T.1    Ulysse, A.2
  • 16
    • 0001756111 scopus 로고
    • The synthesis of oligoribonucleotides. II. The use of silyl protecting groups in nucleoside and nucleotide chemistry. VII
    • Kelvin, K.; Ogilvie, S. L.; Beaucage, S. L. The Synthesis of Oligoribonucleotides. II. The Use of Silyl Protecting Groups in Nucleoside and Nucleotide Chemistry. VII. Can. J. Chem. 1978, 56, 2768-80.
    • (1978) Can. J. Chem. , vol.56 , pp. 2768-2780
    • Kelvin, K.1    Ogilvie, S.L.2    Beaucage, S.L.3
  • 18
    • 0001170949 scopus 로고
    • A convenient and general approach to the synthesis of properly protected D-nucleoside-3′-hydrogen-phosphonates via phosphite intermediates
    • Marugg, J. E.; Tromp, M.; Kuyl-Yeheskiely, E.; van der Marel, G. A.; van Boom, J. H. A Convenient and General Approach to the Synthesis of Properly Protected D-Nucleoside-3′-Hydrogen-phosphonates via Phosphite Intermediates. Tetrahedron Lett. 1986, 27, 2661-4.
    • (1986) Tetrahedron Lett. , vol.27 , pp. 2661-2664
    • Marugg, J.E.1    Tromp, M.2    Kuyl-Yeheskiely, E.3    Van Der Marel, G.A.4    Van Boom, J.H.5
  • 19
    • 49149135789 scopus 로고
    • Deoxynucleoside phosphoramidites. A new class of key intermediates for deoxypolynucleotide synthesis
    • Beaucage, S. L.; Caruther, M. H. Deoxynucleoside Phosphoramidites. A New Class of Key Intermediates for Deoxypolynucleotide Synthesis. Tetrahedron Lett. 1981, 22, 1859-62.
    • (1981) Tetrahedron Lett. , vol.22 , pp. 1859-1862
    • Beaucage, S.L.1    Caruther, M.H.2
  • 20
    • 0001210399 scopus 로고
    • Ribonucleotide analogs having novel internucleotide linkage
    • Nemer, M. J.; Ogilvie, K. K. Ribonucleotide Analogs Having Novel Internucleotide Linkage. Tetrahedron Lett. 1980, 21, 4149-52.
    • (1980) Tetrahedron Lett. , vol.21 , pp. 4149-4152
    • Nemer, M.J.1    Ogilvie, K.K.2
  • 21
    • 0023022990 scopus 로고
    • Deoxynucleoside H-phosphonate diester intermediates in the synthesis of internucleotide phosphate analogues
    • Froehler, B. C. Deoxynucleoside H-phosphonate Diester Intermediates in the Synthesis of Internucleotide Phosphate Analogues. Tetrahedron Lett. 1986, 27, 5575-8.
    • (1986) Tetrahedron Lett. , vol.27 , pp. 5575-5578
    • Froehler, B.C.1
  • 22
    • 85066045586 scopus 로고
    • Phase-transfer-catalysed phosphorylation of amines in an aqueous system
    • Zweirzak, A. Phase-transfer-catalysed Phosphorylation of Amines in an Aqueous System. Synthesis 1975, 507-9.
    • (1975) Synthesis , pp. 507-509
    • Zweirzak, A.1
  • 23
    • 0014276040 scopus 로고
    • The use of β-methylthioethyl esters for the protection of carboxy groups in peptide synthesis: Removal through the β-methylsulfonylethyl ester
    • Hardy, P. M.; Rydon, H. N.; Thompson, R. C. The Use of β-Methylthioethyl Esters for the Protection of carboxy Groups in Peptide Synthesis: Removal through the β-Methylsulfonylethyl Ester. Tetrahedron Lett. 1968, 21, 2525-6.
    • (1968) Tetrahedron Lett. , vol.21 , pp. 2525-2526
    • Hardy, P.M.1    Rydon, H.N.2    Thompson, R.C.3
  • 24
    • 0025149019 scopus 로고
    • Crystal structure of Eseherichia coli thymidylate synthase containing bound 5-fluoro-2′-deoxyuridylate and 10-propargyl-5,8-dideazafolate
    • Matthews, D, A.; Appelt, K.; Oatley, S. J.; Xuong, N. H. Crystal Structure of Eseherichia Coli Thymidylate Synthase Containing Bound 5-Fluoro-2′-Deoxyuridylate and 10-Propargyl-5,8-Dideazafolate. J. Mol. Biol. 1990, 214, 923-36.
    • (1990) J. Mol. Biol. , vol.214 , pp. 923-936
    • Matthews, D.A.1    Appelt, K.2    Oatley, S.J.3    Xuong, N.H.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.