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Volumn 45, Issue 1, 2010, Pages 244-255

Synthesis of aryl phosphates based on pyrimidine and triazine scaffolds

Author keywords

1,3,5 Triazines; 2 Aminopyrimidines; Aryl phosphates; De novo design; Grb2 SH2 domain; Heck reaction; Protein tyrosine kinases; Suzuki Miyaura reaction

Indexed keywords

1 (4 CYANOPHENYL)GUANIDINE; 2 [4 CHLORO 6 (4 HYDROXYPHENYLAMINO) 1,3,5 TRIAZIN 2 YLAMINO]ACETAMIDE; 2 [4 [2 (4 PHOSPHORYLOXYPHENOXY)PHENYL] 6 (4 PHOSPHORYLOXYPHENYLAMINO) 1,3,5 TRIAZIN 2 YLAMINO]ACETAMIDE; 2 [4 [3 (4 PHOSPHORYLOXYPHENOXY)PHENYL] 6 (4 PHOSPHORYLOXYPHENYLAMINO) 1,3,5 TRIAZIN 2 YLAMINO]ACETAMIDE; 4 [3 (4 BENZYLOXYPHENOXY)PHENYL]BUT 3 EN 2 ONE; 4 [3 [2 [4 (2H TETRAZOL 5 YL)PHENYLAMINO] 6 METHYLPYRIMIDIN 4 YL]PHENOXY]PHENYL DIHYDROGEN PHOSPHATE; ACETAMIDE DERIVATIVE; ALKANONE; GUANIDINE; PHOSPHATE; PYRIMIDINE; TRIAZINE; UNCLASSIFIED DRUG;

EID: 72049092280     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2009.10.003     Document Type: Article
Times cited : (16)

References (95)
  • 8
    • 33748684468 scopus 로고    scopus 로고
    • For a review on applications of cyanuric chloride in organic synthesis, see: and references 1-6 cited therein
    • For a review on applications of cyanuric chloride in organic synthesis, see:. Blotny G. Tetrahedron 62 (2006) 9507-9522 and references 1-6 cited therein
    • (2006) Tetrahedron , vol.62 , pp. 9507-9522
    • Blotny, G.1
  • 23
    • 0028938153 scopus 로고    scopus 로고
    • For the crystal structure of the mammalian Grb2 adaptor which is deposited in the Protein Data Bank under the accession code 1GRI, see:
    • For the crystal structure of the mammalian Grb2 adaptor which is deposited in the Protein Data Bank under the accession code 1GRI, see:. Maignan S., Guilloteau J.P., Fromage N., Arnoux B., Becquart J., and Ducruix A. Science 268 (1996) 291-293
    • (1996) Science , vol.268 , pp. 291-293
    • Maignan, S.1    Guilloteau, J.P.2    Fromage, N.3    Arnoux, B.4    Becquart, J.5    Ducruix, A.6
  • 25
    • 0033539113 scopus 로고    scopus 로고
    • For molecular modeling of ligand 1 binding mode to Grb2 SH2, see:
    • For molecular modeling of ligand 1 binding mode to Grb2 SH2, see:. Liu W.-Q., Vidal M., Gresh N., Roques B.P., and Garbay C. J. Med. Chem. 42 (1999) 3737-3741
    • (1999) J. Med. Chem. , vol.42 , pp. 3737-3741
    • Liu, W.-Q.1    Vidal, M.2    Gresh, N.3    Roques, B.P.4    Garbay, C.5
  • 30
    • 85083129582 scopus 로고    scopus 로고
    • note
    • X ray crystallographic data are deposited in the Protein Data Bank under the accession codes 2HUW and 2HUY. This latter was obseleted on 2008-08-12 and superceded by 3C7I.
  • 31
    • 7744243992 scopus 로고    scopus 로고
    • For reviews on tetrazoles as carboxylic acid isosteres, see:
    • For reviews on tetrazoles as carboxylic acid isosteres, see:. Patani G.A., and LaVoie E.J. Chem. Rev. 96 (1996) 3147-3176
    • (1996) Chem. Rev. , vol.96 , pp. 3147-3176
    • Patani, G.A.1    LaVoie, E.J.2
  • 33
    • 85083141745 scopus 로고    scopus 로고
    • A Scifinder search on the triazine scaffold incorporating a bis-aryl phosphate exclusively identified two patents, on triazine dyes, see: B.L. McConnell, R. Thornton, L.A. Graham, U.S. US 4091004 19780523; 1978 and ref, 34
    • A Scifinder search on the triazine scaffold incorporating a bis-aryl phosphate exclusively identified two patents, on triazine dyes, see: B.L. McConnell, R. Thornton, L.A. Graham, U.S. US 4091004 19780523; 1978 and ref. [34].
  • 34
    • 85083147723 scopus 로고    scopus 로고
    • K. Sato, H. Tanaka, Jpn. Kokai Tokkyo Koho. JP 04117369 A 19920417 Heisei. CAN 117:152766 AN 1992:552766; 1992.
    • K. Sato, H. Tanaka, Jpn. Kokai Tokkyo Koho. JP 04117369 A 19920417 Heisei. CAN 117:152766 AN 1992:552766; 1992.
  • 36
    • 85083142460 scopus 로고    scopus 로고
    • For compound 8, see: A Scifinder search exclusively identified three patents. P. Furet, P. Imbach, T.M. Ramsey, A. Schlapbach, D. Scholz, G. Caravatti, PCT Int. Appl. WO 2004005282; 2004
    • For compound 8, see: A Scifinder search exclusively identified three patents. P. Furet, P. Imbach, T.M. Ramsey, A. Schlapbach, D. Scholz, G. Caravatti, PCT Int. Appl. WO 2004005282; 2004.
  • 38
    • 85083143406 scopus 로고    scopus 로고
    • For compound 10, see: C.F. Claiborne, L.J. Payne, R.J. Boyce, T.B. Sells, S.G. Stroud, S. Travers, T.J. Vos, G.S. Weatherhead, U.S. Pat. Appl. Publ. US 20050256102; 2005.
    • For compound 10, see: C.F. Claiborne, L.J. Payne, R.J. Boyce, T.B. Sells, S.G. Stroud, S. Travers, T.J. Vos, G.S. Weatherhead, U.S. Pat. Appl. Publ. US 20050256102; 2005.
  • 47
    • 0001605858 scopus 로고
    • and references cited therein
    • Sandler S.R. J. Org. Chem. 35 (1970) 3967-3968 and references cited therein
    • (1970) J. Org. Chem. , vol.35 , pp. 3967-3968
    • Sandler, S.R.1
  • 51
    • 85083141305 scopus 로고    scopus 로고
    • For the preparation of 2,4,6-tricyano-1,3,5-triazine TCT, see: G. Beck, United States Patent 5086172; 1992
    • For the preparation of 2,4,6-tricyano-1,3,5-triazine (TCT), see: G. Beck, United States Patent 5086172; 1992.
  • 55
    • 7044231364 scopus 로고    scopus 로고
    • To the best of our knowledge, only one report mentioned the monocoupling reaction of organoboronic acids with 2,4,6-trichloro-1,3,5-triazine, see:
    • To the best of our knowledge, only one report mentioned the monocoupling reaction of organoboronic acids with 2,4,6-trichloro-1,3,5-triazine, see:. Tan J.-Q., Chang J.-H., and Deng M.-Z. Chin. J. Chem. 22 (2004) 941-944
    • (2004) Chin. J. Chem. , vol.22 , pp. 941-944
    • Tan, J.-Q.1    Chang, J.-H.2    Deng, M.-Z.3
  • 70
    • 26444537021 scopus 로고    scopus 로고
    • For a previous work on the displacement of aryl fluorides with hydroquinone, see:
    • For a previous work on the displacement of aryl fluorides with hydroquinone, see:. Marcune B.F., Hillier M.C., Marcoux J.-F., and Humphrey G.R. Tetrahedron Lett. 46 (2005) 7823-7826
    • (2005) Tetrahedron Lett. , vol.46 , pp. 7823-7826
    • Marcune, B.F.1    Hillier, M.C.2    Marcoux, J.-F.3    Humphrey, G.R.4
  • 72
    • 85083120645 scopus 로고    scopus 로고
    • note
    • 3): m/z 417, 419, 421], resulting from the reaction of hydroquinone as an aryloxide C-nucleophile, and an unidentified compound.
  • 73
    • 4143103592 scopus 로고    scopus 로고
    • For an alternative method (i.e., a copper-catalyzed arylboronic acid-heteroatom coupling) to access such a boronic acid, see:
    • For an alternative method (i.e., a copper-catalyzed arylboronic acid-heteroatom coupling) to access such a boronic acid, see:. Pennington T.E., Kardiman C., and Hutton C.A. Tetrahedron Lett. 45 (2004) 6657-6660
    • (2004) Tetrahedron Lett. , vol.45 , pp. 6657-6660
    • Pennington, T.E.1    Kardiman, C.2    Hutton, C.A.3
  • 75
    • 0037029806 scopus 로고    scopus 로고
    • For an adaptation of the phosphorylation procedure described by Silverberg et al. [74] for solid-phase synthesis, see:
    • For an adaptation of the phosphorylation procedure described by Silverberg et al. [74] for solid-phase synthesis, see:. Deprez P., Mandine E., Gofflo D., Meunier S., and Lesuisse D. Bioorg. Med. Chem. Lett. 12 (2002) 1295-1298
    • (2002) Bioorg. Med. Chem. Lett. , vol.12 , pp. 1295-1298
    • Deprez, P.1    Mandine, E.2    Gofflo, D.3    Meunier, S.4    Lesuisse, D.5
  • 83
    • 0030957530 scopus 로고    scopus 로고
    • For an example of the Heck reaction of halogeno-diphenyl ethers with ethyl acrylate, see:
    • For an example of the Heck reaction of halogeno-diphenyl ethers with ethyl acrylate, see:. Orr G.F., Musso D.L., Kelley J.L., Joyner S.S., Davis S.T., and Baccanari D.P. J. Med. Chem. 40 (1997) 1179-1185
    • (1997) J. Med. Chem. , vol.40 , pp. 1179-1185
    • Orr, G.F.1    Musso, D.L.2    Kelley, J.L.3    Joyner, S.S.4    Davis, S.T.5    Baccanari, D.P.6
  • 85
    • 0034729476 scopus 로고    scopus 로고
    • For the thermal polymerization of a vinyl ketone during the Heck reaction, see:
    • For the thermal polymerization of a vinyl ketone during the Heck reaction, see:. Uchiro H., Nagasawa K., Aiba Y., and Kobayashi S. Tetrahedron Lett. 41 (2000) 4165-4168
    • (2000) Tetrahedron Lett. , vol.41 , pp. 4165-4168
    • Uchiro, H.1    Nagasawa, K.2    Aiba, Y.3    Kobayashi, S.4
  • 86
    • 0001266786 scopus 로고    scopus 로고
    • For the value of α,β-unsaturated ketones as key intermediates for the synthesis of pyrimidines on the solid phase, see:
    • For the value of α,β-unsaturated ketones as key intermediates for the synthesis of pyrimidines on the solid phase, see:. Marzinzik A.L., and Felder E.R.J. Org. Chem. 63 (1998) 723-727
    • (1998) Org. Chem. , vol.63 , pp. 723-727
    • Marzinzik, A.L.1    Felder, E.R.J.2
  • 90
    • 85083151915 scopus 로고    scopus 로고
    • note
    • 50 = 174 μM): see, XXth International Symposium on Medicinal Chemistry, August 31- September 4, 2008, Vienna, Austria. Poster Presentation P527 Development of non-peptide inhibitors of Her2-Grb2 interaction using molecular modeling and NMR spectroscopy. M.L. López-Rodriguez, S. Ortega-Gutiérrez, B. Benhamú, Á.L. Orcajo, P. Serrano, A.Viso, I.R. Torrecillas, M. Campillo, L. Pardo, K. Wüthrich.
  • 91
    • 85083142053 scopus 로고    scopus 로고
    • See Supporting information
    • See Supporting information.
  • 92
    • 85083136962 scopus 로고    scopus 로고
    • note
    • Low-temperature molecular dynamics (300 steps of 5 picoseconds each, T = 100 K, ε = 4.) were done with the Discover module and the Cff91 force-field of the Insight II package (Accelrys, Inc). We resorted to the crystal structure of the complex of 1 with Grb2-SH2 to dock 1 and all non-peptidic compounds in the binding site.


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