Copyright (c) 2014 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
Synthesis of 6-Piperazinyl-3,4-dihydroquinazolin-2(1H)-ones
Corresponding Author(s) : N. Ullah
Asian Journal of Chemistry,
Vol. 26 No. 7 (2014): Vol 26 Issue 7
Abstract
A series of new 6-piperazinyl-3,4-dihydroquinazolin-2(1H)-ones have been synthesized. The described compounds are structurally related to adoprazine, a potential atypical antipsychotics bearing potent D2 receptor antagonist and 5-HT1A receptor agonist properties. Buchwald-Hartwig coupling of suitably modified aryl bromides with tert-butyl piperazine-1-carboxylate afforded the advanced intermediate piperazinyl-3,4-dihydroquinazolin-2(1H)-one. The reductive amination of the latter with appropriately designed biarylaldehydes accomplished the synthesis of 6-piperazinyl-3,4-dihydroquinazolin-2(1H)-ones.
Keywords
Download Citation
Endnote/Zotero/Mendeley (RIS)BibTeX
- Diagnostic and Statistical Manual of Mental Disorders, Text Revision, American Psychiatric Association, Washington, DC, edn 4, pp. 297-343 (2000).
- D.C. Goff and R.I. Shader, in eds.: S.R. Hirsch and D. Weinberger, Non-Neurological Side-Effects of Antipsychotic Drugs, In: Schizophrenia, Blackwell Publishing, Oxford, edn 2, p. 573-88 (2002).
- H.Y. Meltzer, Psychopharmacology , 99(S1), S18 (1989); doi:10.1007/BF00442554.
- L.H. Lindstrom, Acta Psychiatr. Scand., 77, 524 (1988); doi:10.1111/j.1600-0447.1988.tb05164.x.
- E.P. Prinssen, F.C. Colpaert and W. Koek, Eur. J. Pharmacol., 453, 217 (2002); doi:10.1016/S0014-2999(02)02430-5.
- A. Newman-Tancredi, M.B. Assie, N. Leduc, A.M. Ormiere, N. Danty and C. Cosi, Int. J. Neuropsychopharmacol., 8, 341 (2005); doi:10.1017/S1461145704005000.
- M.B. Assie, V. Ravailhe, V. Faucillon and A. Newman-Tancredi, J. Pharmacol. Exp. Ther., 315, 265 (2005); doi:10.1124/jpet.105.087163.
- L.A. Bruins Slot, L. De Vries, A. Newman-Tancredi and D. Cussac, Eur. J. Pharmacol., 534, 63 (2006); doi:10.1016/j.ejphar.2006.01.027.
- L.A. Bruins Slot, M.S. Kleven and A. Newman-Tancredi, Neuropharmacology, 49, 996 (2005); doi:10.1016/j.neuropharm.2005.05.013.
- M.S. Kleven, C. Barret-Grevoz, L.A.B. Slot and A. Newman-Tancredi, Neuropharmacology, 49, 135 (2005); doi:10.1016/j.neuropharm.2005.02.005.
- R.A. Bantick, J.F.W. Deakin and P.M. Grasby, J. Psychopharmacol., 15, 37 (2001); doi:10.1177/026988110101500108.
- A.C. McCreary, J.C. Glennon, C.R. Ashby Jr., H.Y. Meltzer, Z. Li, J.-H. Reinders, M.B. Hesselink, S.K. Long, A.H. Herremans, H. van Stuivenberg, R.W. Feenstra and C.G. Kruse, Neuropsychopharmacology, 32, 78 (2007); doi:10.1038/sj.npp.1301098.
- A. Newman-Tancredi, Curr. Opin. Investig. Drugs, 11, 802 (2010).
- S. Cuisiat, N. Bourdiol, V. Lacharme, A. Newman-Tancredi, F. Colpaert and B. Vacher, J. Med. Chem., 50, 865 (2007); doi:10.1021/jm061180b.
- N. Ullah, Z. Naturforsch, 67, 75 (2012); doi:10.5560/ZNB.2012.67b0075.
- N. Ullah and A.A.Q. Al-Shaheri, Z. Naturforsch, 67, 253 (2012); doi:10.5560/ZNB.2012.67b0253.
- N. Ullah, J. Enzym. Inhib. Med. Chem., 29, 281 (2014); doi:10.3109/14756366.2013.776556.
- H. Venkatesan, F.M. Hocutt, T.K. Jones and M.H. Rabinowitz, J. Org. Chem., 75, 3488 (2010); doi:10.1021/jo100392x.
References
Diagnostic and Statistical Manual of Mental Disorders, Text Revision, American Psychiatric Association, Washington, DC, edn 4, pp. 297-343 (2000).
D.C. Goff and R.I. Shader, in eds.: S.R. Hirsch and D. Weinberger, Non-Neurological Side-Effects of Antipsychotic Drugs, In: Schizophrenia, Blackwell Publishing, Oxford, edn 2, p. 573-88 (2002).
H.Y. Meltzer, Psychopharmacology , 99(S1), S18 (1989); doi:10.1007/BF00442554.
L.H. Lindstrom, Acta Psychiatr. Scand., 77, 524 (1988); doi:10.1111/j.1600-0447.1988.tb05164.x.
E.P. Prinssen, F.C. Colpaert and W. Koek, Eur. J. Pharmacol., 453, 217 (2002); doi:10.1016/S0014-2999(02)02430-5.
A. Newman-Tancredi, M.B. Assie, N. Leduc, A.M. Ormiere, N. Danty and C. Cosi, Int. J. Neuropsychopharmacol., 8, 341 (2005); doi:10.1017/S1461145704005000.
M.B. Assie, V. Ravailhe, V. Faucillon and A. Newman-Tancredi, J. Pharmacol. Exp. Ther., 315, 265 (2005); doi:10.1124/jpet.105.087163.
L.A. Bruins Slot, L. De Vries, A. Newman-Tancredi and D. Cussac, Eur. J. Pharmacol., 534, 63 (2006); doi:10.1016/j.ejphar.2006.01.027.
L.A. Bruins Slot, M.S. Kleven and A. Newman-Tancredi, Neuropharmacology, 49, 996 (2005); doi:10.1016/j.neuropharm.2005.05.013.
M.S. Kleven, C. Barret-Grevoz, L.A.B. Slot and A. Newman-Tancredi, Neuropharmacology, 49, 135 (2005); doi:10.1016/j.neuropharm.2005.02.005.
R.A. Bantick, J.F.W. Deakin and P.M. Grasby, J. Psychopharmacol., 15, 37 (2001); doi:10.1177/026988110101500108.
A.C. McCreary, J.C. Glennon, C.R. Ashby Jr., H.Y. Meltzer, Z. Li, J.-H. Reinders, M.B. Hesselink, S.K. Long, A.H. Herremans, H. van Stuivenberg, R.W. Feenstra and C.G. Kruse, Neuropsychopharmacology, 32, 78 (2007); doi:10.1038/sj.npp.1301098.
A. Newman-Tancredi, Curr. Opin. Investig. Drugs, 11, 802 (2010).
S. Cuisiat, N. Bourdiol, V. Lacharme, A. Newman-Tancredi, F. Colpaert and B. Vacher, J. Med. Chem., 50, 865 (2007); doi:10.1021/jm061180b.
N. Ullah, Z. Naturforsch, 67, 75 (2012); doi:10.5560/ZNB.2012.67b0075.
N. Ullah and A.A.Q. Al-Shaheri, Z. Naturforsch, 67, 253 (2012); doi:10.5560/ZNB.2012.67b0253.
N. Ullah, J. Enzym. Inhib. Med. Chem., 29, 281 (2014); doi:10.3109/14756366.2013.776556.
H. Venkatesan, F.M. Hocutt, T.K. Jones and M.H. Rabinowitz, J. Org. Chem., 75, 3488 (2010); doi:10.1021/jo100392x.