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This work is licensed under a Creative Commons Attribution 4.0 International License.
Synthesis and Characterization of 4-Amino-quinazoline Derivatives
Corresponding Author(s) : Ju-Cheng Zhang
Asian Journal of Chemistry,
Vol. 27 No. 7 (2015): Vol 27 Issue 7, 2015
Abstract
Four 4-amino-quinazoline compounds, including 7-[3-(2-methoxyphenoxy)propoxy]-N'-(3-chlorophenyl)-6-methoxyquinazolin-4-amine, 7-[3-(4-methoxyphenoxy)propoxy]-N'-(3-chlorophenyl)-6-methoxyquinazolin-4-amine, 2-[3-{4-(3-chlorophenylamino)-6-methoxy-quinazolin-7-yloxy}propoxy]benzaldehyde, 4-[3-{4-(3-chlorophenylamino)-6-methoxyquinazolin-7-yloxy}propoxy]benzaldehyde, were synthesized from N'-[5-(3-chloropropoxy)-2-cyano-4-methoxyphen-yl]-N,N-dimethylformamidine by cyclization and etheration. The yields of the compounds IIIa-d were 70.3, 71.0, 45.5 and 50.2 %, respectively. Their structures were characterized by IR, 1H NMR, 13C NMR, MS and elemental analysis.
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References
N.V. Sergina and M.M. Moasser, Trends Mol. Med., 13, 527 (2007); doi:10.1016/j.molmed.2007.10.002.
N.E. Hynes and H.A. Lane, Nat. Rev. Cancer, 5, 341 (2005); doi:10.1038/nrc1609.
M.M. Moasser, Oncogene, 26, 6577 (2007); doi:10.1038/sj.onc.1210478.
M.M. Moasser, Oncogene, 26, 6469 (2007); doi:10.1038/sj.onc.1210477.
A.W. Burgess, H.-S. Cho, C. Eigenbrot, K.M. Ferguson, T.P.J. Garrett, D.J. Leahy, M.A. Lemmon, M.X. Sliwkowski, C.W. Ward and S. Yokoyama, Mol. Cell, 12, 541 (2003); doi:10.1016/S1097-2765(03)00350-2.
R.S. Herbst and C.J. Langer, Semin. Oncol., 29, 27 (2002); doi:10.1053/sonc.2002.31525.
P. Traxler, G. Bold, E. Buchdunger, G. Caravatti, P. Furet, P. Manley, T. O’Reilly, J. Wood and J. Zimmermann, J. Med. Res. Rev., 21, 499 (2001); doi:10.1002/med.1022.
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F. Ciardiello and G. Tortora, Clin. Cancer Res., 7, 2958 (2001).
S. Maheswaran, L.V. Sequist, S. Nagrath, L. Ulkus, B. Brannigan, C.V. Collura, E. Inserra, S. Diederichs, A.J. Iafrate, D.W. Bell, S. Digumarthy, A. Muzikansky, D. Irimia, J. Settleman, R.G. Tompkins, T.J. Lynch, M. Toner and D.A. Haber, Engl. J. Med., 359, 366 (2008); doi:10.1056/NEJMoa0800668.
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(a) H.R. Tsou, E.G. Overbeek-Klumpers, W.A. Hallett, M.F. Reich, M.B. Floyd, B.D. Johnson, R.S. Michalak, R. Nilakantan, C. Discafani, J. Golas, S.K. Rabindran, R. Shen, X. Shi, Y.-F. Wang, J. Upeslacis and A. Wissner, J. Med. Chem., 48, 1107 (2005); doi:10.1021/jm040159c; (b) S.K. Rabindran, C.M. Discafani, E.C. Rosfjord, M. Baxter, M.B. Floyd, J. Golas, W.A. Hallett, B.D. Johnson, R. Nilakantan, E. Overbeek, M.F. Reich, R. Shen, X. Shi, H.-R. Tsou, Y.-F. Wang and A. Wissner, Cancer Res., 64, 3958 (2004); doi:10.1158/0008-5472.CAN-03-2868.
A. Wissner, E. Overbeek, M.F. Reich, M.B. Floyd, B.D. Johnson, N. Mamuya, E.C. Rosfjord, C. Discafani, R. Davis, X. Shi, S.K. Rabindran, B.C. Gruber, F. Ye, W.A. Hallett, R. Nilakantan, R. Shen, Y.-F. Wang, L.M. Greenberger and H.-R. Tsou, J. Med. Chem., 46, 49 (2003); doi:10.1021/jm020241c.
(a) J.B. Smaill, H.D.H. Showalter, H. Zhou, A.J. Bridges, D.J. McNamara, D.W. Fry, J.M. Nelson, V. Sherwood, P.W. Vincent, B.J. Roberts, W.L. Elliott and W.A. Denny, J. Med. Chem., 44, 429 (2001); doi:10.1021/jm000372i; (b) S. Campos, O. Hamid, M.V. Seiden, A. Oza, M. Plante, R.K. Potkul, P.F. Lenehan, E.P. Kaldjian, M.L. Varterasian, C. Jordan, C. Charbonneau and H. Hirte, J. Clin. Oncol., 23, 5597 (2005); doi:10.1200/JCO.2005.08.091.
B.P. Rubin and A. Duensing, Lab. Invest., 86, 981 (2006); doi:10.1038/labinvest.3700466.
X. Cai, H.-X. Zhai, J. Wang, J. Forrester, H. Qu, L. Yin, C.-J. Lai, R. Bao and C. Qian, J. Med. Chem., 53, 2000 (2010); doi:10.1021/jm901453q.
Y. Heping and O. Guiping, Chin. J. Org. Chem., 31, 901 (2011).
H.P. Yan, D.S. Huang and J.C. Zhang, Adv. Mater. Res., 634-638, 1215 (2013); doi:10.4028/www.scientific.net/AMR.634-638.1215.
L.F. Hennequin, A.P. Thomas, C. Johnstone, E.S.E. Stokes, P.A. Plé, J.-J.M. Lohmann, D.J. Ogilvie, M. Dukes, S.R. Wedge, J.O. Curwen, J. Kendrew and C. Lambert-van der Brempt, J. Med. Chem., 42, 5369 (1999); doi:10.1021/jm990345w.
L.F. Hennequin, E.S.E. Stokes, A.P. Thomas, C. Johnstone, P.A. Plé, D.J. Ogilvie, M. Dukes, S.R. Wedge, J. Kendrew and J.O. Curwen, J. Med. Chem., 45, 1300 (2002); doi:10.1021/jm011022e.
C. Ditchfield, V.L. Johnson and A. Tighe, J. Cell Biol., 161, 267 (2003); doi:10.1083/jcb.200208091.
P.A. Ple´, T.P. Green, L.F. Hennequin, J. Curwen, M. Fennell, J. Allen, C. Lambert-van der Brempt and G. Costello, J. Med. Chem., 47, 871 (2004); doi:10.1021/jm030317k.
L.F. Hennequin, J. Allen, J. Breed, J. Curwen, M. Fennell, T.P. Green, C. Lambert-van der Brempt, R. Morgentin, R.A. Norman, A. Olivier, L. Otterbein, P.A. Plé, N. Warin and G. Costello, J. Med. Chem., 49, 6465 (2006); doi:10.1021/jm060434q.
K.M. Foote, A.A. Mortlock, N.M. Heron, F.H. Jung, G.B. Hill, G. Pasquet, M.C. Brady, S. Green, S.P. Heaton, S. Kearney, N.J. Keen, R. Odedra, S.R. Wedge and R.W. Wilkinson, Bioorg. Med. Chem. Lett., 18, 1904 (2008); doi:10.1016/j.bmcl.2008.02.002.
R. Al-Salahi, M. Marzouk, A.E. Ashour and I. Alswaidan, Asian J. Chem., 26, 2173 (2014); doi:10.14233/ajchem.2014.16849.
R. Gupta and R.P. Chaudhary, Asian J. Chem., 24, 2113 (2012).