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Number of results

Journal

2013 | 11 | 8 | 1278-1285

Article title

The first synthesis of 3-deoxyoripavine and its utilization in the preparation of 10-deoxyaporphines and cyprodime

Content

Title variants

Languages of publication

EN

Abstracts

EN
The synthesis of 3-deoxyoripavine (7) was realized as a novel and promising intermediate towards the synthesis of the important class of dopaminergic and/or serotonergic 10-deoxyaporphines and the special pharmacological tool µ opioid antagonist cyprodime. Generally, the preparation of these valuable biologically active compounds was achieved in remarkable yields. [...]

Publisher

Journal

Year

Volume

11

Issue

8

Pages

1278-1285

Physical description

Dates

published
1 - 8 - 2013
online
1 - 6 - 2013

Contributors

author
  • Department of Pharmaceutical Chemistry, Medical and Health Science Centre, University of Debrecen, H-4010, Debrecen, Hungary
author
  • Department of Physical Chemistry, University of Debrecen, H-4010, Debrecen, Hungary
  • Department of Organic Chemistry, University of Debrecen, H-4010, Debrecen, Hungary

References

  • [1] M.H. Hedberg, A.M. Johansson, G. Nordvall, A. Yliniemela, H.B. Li, A.R. Martin, S. Hjorth, L. Unelius, S. Sundell, H. Hacksell, J. Med. Chem. 38, 647 (1995) http://dx.doi.org/10.1021/jm00004a011[Crossref]
  • [2] Y.-G. Si, M.P. Gardner, F.I. Tarazi, R.J. Baldessarini, J.L. Neumeyer, J. Med. Chem. 51, 983 (2008) http://dx.doi.org/10.1021/jm701045j[Crossref]
  • [3] Y.-G. Si, Y.-K. Choi, M.P. Gardner, F.I. Tarazi, R.J. Baldessarini, J.L. Neumeyer, Bioorg. Med. Chem. Lett. 19, 51 (2009) http://dx.doi.org/10.1016/j.bmcl.2008.11.025[Crossref]
  • [4] Z. Liu, H. Zhang, N. Ye, J. Zhang, Q.Q. Wu, P. Sun, L. Li, X. Zhen, A. Zhang, J. Med. Chem. 53, 1319 (2010) http://dx.doi.org/10.1021/jm9015763[Crossref]
  • [5] N. Ye, Q.Q. Wu, L. Zhu, L. Zheng, B. Gao, X. Zhen, A. Zhang, A. Bioorg. Med. Chem. 19, 1999 (2011) http://dx.doi.org/10.1016/j.bmc.2011.01.053[Crossref]
  • [6] A.W. Sromek, Y.-G. Si, T. Zhang, S.R. George, P. Seeman, J.L. Neumeyer, ACS Med. Chem. Lett. 2, 189 (2011) http://dx.doi.org/10.1021/ml1001689[Crossref]
  • [7] V.J. Ram, J.L. Neumeyer, J. Het. Chem. 28, 1721 (1991) http://dx.doi.org/10.1002/jhet.5570280713[Crossref]
  • [8] J.G. Cannon, P. Mohan, J. Bojarski, J.P. Long, R.K. Bhatnagar, P.A. Leonard, J.R. Flynn, T.K. Chatterjee, J. Med. Chem. 31, 313 (1988) http://dx.doi.org/10.1021/jm00397a007[Crossref]
  • [9] J.G. Cannon, H. Jackson, J.P. Long, P. Leonard, R.K. Bhatnagar, J. Med. Chem. 32, 1959 (1989) http://dx.doi.org/10.1021/jm00128a044[Crossref]
  • [10] A.G. Millgate, B.J. Pogson, I.W. Wilson, T.M. Kutchan, M.H. Zenk, W.L. Gerlach, A.J. Fist, P.J. Larkin, Nature 431, 413 (2004) http://dx.doi.org/10.1038/431413a[Crossref]
  • [11] S. Berényi, Cs. Csutorás, A. Sipos, Curr. Med. Chem. 16, 3215 (2009) http://dx.doi.org/10.2174/092986709788803295[Crossref]
  • [12] B.-S. Huang, on behalf of Penick Corp. US2008/0125592, 2008. CAN 148:472243
  • [13] J.A.C. Alves, J.V. Barkley, A.F. Brigas, R.A.W. Johnstone, J. Chem. Soc., Perkin Trans. 2, 669 (1997) [Crossref]
  • [14] I.D. Entwistle, B.J. Hussey, R.A.W. Johnstone, Tetrahedron Lett. 21, 4747 (1980) http://dx.doi.org/10.1016/0040-4039(80)88111-1[Crossref]
  • [15] B.J. Hussey, R.A.W. Johnstone, J.D. Entwistle, Tetrahedron 38, 3775 (1982) http://dx.doi.org/10.1016/0040-4020(82)80091-4[Crossref]
  • [16] D. Bethell, R.A.W. Johnstone, P.J. Price, J. Chem. Soc., Chem. Commun. 303 (1985) [Crossref]
  • [17] R.A.W. Johnstone, W.N. McLean, Tetrahedron Lett. 29, 5553 (1988) http://dx.doi.org/10.1016/S0040-4039(00)80811-4[Crossref]
  • [18] S. Cacchi, P.G. Ciattini, E. Morena, G. Ortar, Tetrahedron Lett. 27, 5541 (1986) http://dx.doi.org/10.1016/S0040-4039(00)85262-4[Crossref]
  • [19] A. Mori, T. Mizusaki, T. Ikawa, T. Maegawa, Y. Monguchi, H. Sajiki, H. Chem. Eur. J. 13, 1432 (2007) http://dx.doi.org/10.1002/chem.200601184[Crossref]
  • [20] R. Bognár, Gy. Gaál, P. Kerekes, G. Horváth, M.T. Kovács, Org. Prep. Proc. Int. 6, 305 (1974) http://dx.doi.org/10.1080/00304947409355125[Crossref]
  • [21] L. Small, B.F. Faris, J. Am. Chem. Soc. 56, 1930 (1934) http://dx.doi.org/10.1021/ja01324a031[Crossref]
  • [22] L. Small, J. Org. Chem. 12, 359 (1947) http://dx.doi.org/10.1021/jo01166a023[Crossref]
  • [23] S. Berényi, S. Hosztafi, S. Makleit, I. Molnar, Acta Chim. Hung. 113, 51 (1983)
  • [24] S.Y. Yeh, H.A. Krebs, C.W. Gorodetzky, J. Pharma. Sci. 68, 133 (1979) http://dx.doi.org/10.1002/jps.2600680205[Crossref]
  • [25] Y. Gao, R.J. Baldessarini, N.S. Kula, J.L. Neumeyer, J. Med. Chem. 33, 1800 (1990) http://dx.doi.org/10.1021/jm00168a040[Crossref]
  • [26] S. Berényi, M. Czirják, S. Makleit, J. Chem. Soc. Perkin Trans. I. 2137 (1993) [Crossref]
  • [27] S. Berényi, Cs. Csutorás, S. Makleit, F. Auth, I. Laszlovszky, B. Kiss, E. Kárpáti, M. Lőw, Med. Chem. Res. 7, 509 (1997)
  • [28] M. Tóth, S. Berényi, Cs. Csutorás, N.S. Kula, K. Zhang, R.J. Baldessarini, J.L. Neumeyer, Bioorg. Med. Chem. 14, 1918 (2006) http://dx.doi.org/10.1016/j.bmc.2005.10.049[Crossref]
  • [29] A. Sipos, Cs. Csutorás, S. Berényi, A. Uustare, A. Rinken, A. Bioorg. Med. Chem. 16, 4563 (2008) http://dx.doi.org/10.1016/j.bmc.2008.02.038[Crossref]
  • [30] A. Sipos, S. Berényi, S. Synlett 11, 1703 (2008) http://dx.doi.org/10.1055/s-2008-1078494[Crossref]
  • [31] A. Sipos, L. Girán, H. Mittendorfer, H. Schmidhammer, S. Berényi, Tetrahedron 64, 1023 (2008) http://dx.doi.org/10.1016/j.tet.2007.08.075[Crossref]
  • [32] V.J. Ram, J.L. Neumeyer, J. Het. Chem. 28, 1721 (1991) http://dx.doi.org/10.1002/jhet.5570280713[Crossref]
  • [33] Z. Liu, X. Chen, L. Yu, X. Zhen, A. Zhang, Bioorg. Med. Chem. 16, 6675 (2008) http://dx.doi.org/10.1016/j.bmc.2008.05.077[Crossref]
  • [34] J.L. Neumeyer, Y.-G. Si, A.W. Sromek on behalf of The McLean Hospital Corporation. WO 2011/130530 A1; 20/10/2011. CAN 155:563140
  • [35] A. Udvardy, Zs. Gyulai, A. Sipos, J. Mol. Struct. 1002, 37 (2011) and References therein http://dx.doi.org/10.1016/j.molstruc.2011.06.041
  • [36] H. Schmidhammer, W.P. Burkhard, L. Eggstein-Aeppli, C.F.C. Smith, J. Med. Chem. 32, 418, (1989) http://dx.doi.org/10.1021/jm00122a021[Crossref]
  • [37] F. Ötvös, G. Tóth, H. Schmidhammer, Helv. Chim. Acta 75, 1718 (1992) http://dx.doi.org/10.1002/hlca.19920750524[Crossref]
  • [38] H. Schmidhammer, A.E. Jacobson, L. Atwell, A. Brossi, Helv. Chem. Acta. 64, 2540 (1981) http://dx.doi.org/10.1002/hlca.19810640809[Crossref]
  • [39] R. Krassing, H. Schmidhammer, Heterocylcles 38, 877 (1994) http://dx.doi.org/10.3987/COM-93-S(B)11[Crossref]

Document Type

Publication order reference

Identifiers

YADDA identifier

bwmeta1.element.-psjd-doi-10_2478_s11532-013-0256-x
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