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DOI: 10.1055/s-2004-815949
Syntheses of Some 4-Anilinoquinazoline Derivatives
Publication History
Publication Date:
03 February 2004 (online)
Abstract
Some 4-N-(3′- or 4′-substituted-phenyl)amino-6,7-dimethoxyquinazolines and the corresponding unsubstituted compounds were synthesized from 2-amino-4,5-dimethoxybenzoic acid and the appropriate substituted anilines. Other related quinazolines or their synthetic intermediates were also obtained. A large number of the described quinazolines are new compounds, while the remaining were prepared by a more efficient procedure. The main goal for the synthesis of these compounds comes from the fact that the 4-anilinoquinazoline pharmacophore is an important unit, which is found among the ATP-competitive inhibitors of several protein kinase enzymes.
Key words
4-anilinoquinazolines - quinazolinones - ATP-inhibitors
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Palmer BD.Trumpp-Kallmeyer S.Fry DW.Nelson JM.Showalter HDH.Denny WA. J. Med. Chem. 1997, 40: 1519 - 2
Thompson AM.Murray DK.Elliot WL.Fry DW.Nelson JA.Showalter HDH.Roberts BJ.Vincent PW.Denny WA. J. Med. Chem. 1997, 40: 3915 - 3
Fry DW.Kraber AJ.McMichael A.Ambroso LA.Nelson JM.Leopold WR.Connors RW.Bridges AJ. Science 1994, 265: 1093 - 4
Baselga J.Averbuch SD. Drugs 2000, 60: 33 - 5
Ciardiello F. Drugs 2000, 60: 25 - 6
Rewcastle GW.Denny WA.Bridges AJ.Zhou H.Cody DR.McMichael A.Fry DW. J. Med. Chem. 1995, 38: 3482 - 7
Bridges AJ.Zhou H.Cody DR.Rewcastle GW.McMichael A.Fry DW.Denny WA. J. Med. Chem. 1996, 39: 267 - 8
Rewcastle GW.Murray DK.Elliot WL.Fry DW.Howard CT.Nelson JA.Roberts BJ.Vincent PW.Showalter HDH.Winters RT.Denny WA. J. Med. Chem. 1998, 41: 742 - 9
Fry DW. Pharmacol. Ther. 1999, 82: 207 - 10
Levitzki A. Pharmacol. Ther. 1999, 82: 231 - 11
Fry DW. Annu. Rep. Med. Chem. 1996, 31: 151 - 12
Rewcastle GW.Denny WA.Showalter HDH. Curr. Org. Chem. 2000, 4: 679 - 13
Szczepankiewicz W.Suwi J.ski Bujok R. Tetrahedron 2000, 56: 9343 - 14
Tomisek AJ.Christensen BE. J. Am. Chem. Soc. 1948, 70: 2423 - 15
Zentmyer DT.Wagner EC. J. Org. Chem. 1949, 14: 967 - 16
Errede LA.Oien HT.Yarian DR. J. Org. Chem. 1977, 42: 12 - 17
Yale HL. J. Am. Chem. Soc. 1955, 75: 675 - 18
Girgis NS.Mφller J.Pedersen EB. Chem. Scrip. 1986, 26: 617 - 19
Taylor EC.Ravindranathan RV. J. Org. Chem. 1962, 27: 2622 - 20
Loakes D.Brown DM.Salisbury SA. J. Chem. Soc., Perkin Trans. 1 1999, 1333 - 21
Veldhuyzen WF.Shallop AJ.Jones RA.Rokita SE. J. Am. Chem. Soc. 2001, 123: 11126 - 23
Nishikawa S.Maki S.Nishikimi Y.Kumazawa Z.Kashimura N. Biosci. Biotech. Biochem. 1994, 58: 1709 - 24
Hennequin LF.Thomas AP.Johnstone C.Stokes ESE.Plé PA.Lohmann JJM.Ogilvie DJ.Dukes M.Wedge SR.Curwen JO.Kendrew J.Brempt CL. J. Med. Chem. 1999, 42: 5369
References
Franchini, K., Faculty of Medical Sciences, State University of Campinas, personal communication.