Novel codeinone derivatives via Michael addition of barbituric acids

Tetrahedron Asymmetry

Volumn 20, Issue 3, 2009, Pages 327-334

  Kolev, Tonko ^a   Bakalska, Rumjana ^b   Seidel, Rüediger W ^c   Mayer Figge, Heike ^c   Oppel, Iris M ^c   Spiteller, Michael ^a   Sheldrick, William S ^c   Koleva, Bojidarka B ^c  

^a TU DORTMUND UNIVERSITY   (Germany)

^b UNIVERSITY OF PLOVDIV   (Bulgaria)

^c RUHR UNIVERSITY BOCHUM   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

BARBITURIC ACID DERIVATIVE; CODEINE; THIOBARBITURIC ACID DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; INFRARED SPECTROSCOPY; LINEAR DICHROISM; LIQUID CRYSTAL; MICHAEL ADDITION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTUM CHEMISTRY; SYNTHESIS; THERMAL ANALYSIS; ULTRAVIOLET SPECTROSCOPY; X RAY CRYSTALLOGRAPHY;

EID: 62849111729     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2009.02.005     Document Type: Article

References (50)

1. Erichsen H.K., Hao J.X., and Xu X.J. Pain 116 (2005) 347
2. Gonenne J., Ferber I., and Burton D. Gastroenterology 28 (2005) A94
3. Gruss H.J., Sutton A., and Horton P. Gastroenterology 128 (2005) A465
4. Neri C., Guarna M., and Blanchi E. Med. Sci. Monitor 10 (2004) MS1
5. Hitosugi N., Hatsukari I., Ohno R., Hashimoto K., Mihara S., Mizukami S., Nakamura S., Sakagami H., Nagasaka H., Matsumoto I., and Kawase M. Anesthesiology 98 (2003) 643
6. Anathan S., Khare N.K., Saini S.K., Seitz L.E., Barlett J.L., Davis P., Dersch C.M., Porreca F., Rothman R.B., and Bilsky E.J. J. Med. Chem. 47 (2004) 1400
7. Gringauz A. Introduction to Medicinal Chemistry-How Drugs Act and Why (1997), Wiley-VCH, New York
8. Koike T., Takashige M., Kimura E., Fujioka H., and Shiro M. Chem. Eur. J. 2 (1996) 617
9. Chin T., Gao Z., Lelouche I., Shin K., Purandare A., Knapp S., and Isied S. J. Am. Chem. Soc. 119 (1997) 12849
10. Marder S.R., Beratan D.N., and Cheng L.-T. Science (1991) 252
11. Marder S.R., Cheng L.-T., Tiemann B.G., Friedli A.C., Blanchard-Desce M., Perry J.W., and Skindhøj J. Science 263 (1994) 511
12. Adamson J., Coe B.J., Grassam H.L., Jeffery J.C., Coles S.J., and Hursthouse M.B. J. Chem. Soc., Perkin Trans. 1 (1999) 2483
13. M{cyrillic}skwin A{cyrillic}.V{cyrillic}., and Reznikova N{cyrillic}.R{cyrillic}. J. Org. Chem. 38 (2002) 487
14. Ahmed M.G., Romman U.K.R., Ahmed S.M., Akhter K., Halim M., and Salauddin M. Bang. J. Sci. Ind. Res. 41 (2006) 119
15. King W., Penprase W.G., and Kloetzel M.C. J. Org. Chem. 26 (1961) 3558
16. Seki I. Chem. Pharm. Bull. 18 (1970) 671
17. Kotick M.P., Leland D.L., Polazzi J.O., and Schut R.N. J. Med. Chem. 23 (1980) 166
18. Kotick M.P., and Polazzi J.O. J. Heterocycl. Chem. 18 (1981) 1029
19. Kotick M.P. J. Med. Chem. 24 (1981) 722
20. Chozland F., Maroni P., Viloria I., and Cros I. Eur. J. Med. Chem.-Chim. Ther. (1983) 18
21. Wongweichintana C., Holt E.M., and Purdie N. Acta Crystallogr., Sect. C 40 (1984) 1486
22. Gylbert L. Acta Crystallogr., Sect. B 29 (1973) 1630
23. Mackay M., and Hodgkin D.C. J. Chem. Soc. (1955) 3261
24. Kartha G., Ahmed F.R., and Barnes W.H. Acta Crystallogr. 15 (1962) 326
25. Barnes L. Can. J. Chem. 33 (1955) 565
26. Grant A., Zacharias D., Mascavage L., Kemmerer G., and Dalton D. J. Heterocycl. Chem. 30 (1993) 553
27. Gelders Y.G., De Ranter C.J., and van Rooijen-Reiss C. Cryst. Struct. Commun. 8 (1979) 995
28. Duchamp D.J., Olson E.C., and Chidester C.G. ACA, Ser. 2 5 (1977) 83
29. Kobylecki R.J., Lane A.C., Smith C.F.C., Wakelin L.P.G., Cruse W.B.T., Egert E., and Kennard O. J. Med. Chem. 29 (1986) 1278
30. Urbanczyk-Lipkowska Z. Acta Crystallogr., Sect. C 51 (1995) 1184
31. Seidel, R. W.; Bakalska, B.R.; Kolev, T.; Vassilev, D.; Mayer-Figge, H.; Spiteller, M.; Sheldrick, W.S.; Koleva, B.B. Spectrochim. Acta, Part A, submitted for publication.
32. Ivanova B.B., Kolev T., and Zareva S.Y. Biopolymers 82 (2006) 587
33. Koleva B.B., Kolev T.M., and Spiteller M. Biopolymers 83 (2006) 498
34. Koleva B.B., Kolev Ts., and Spiteller M. Inorg. Chim. Acta 360 (2007) 2224
35. Bakalska R.I., Chervenkova V.B., and Venkov A. Scientific Works-Chem. 29 (2000) 67
36. Reichardt C. Solvents and Solvent Effects in Organic Chemistry. 3rd ed. (2003), Wiley-VCH Verlag GmbH
37. Whiting J.E., and Edward J.T. Can. J. Chem. 49 (1971) 3799
38. Langhals H. Angew. Chem. 94 (1982) 739
39. Samet A.V., Yamskov A.N., Ugrak B.I., and Semenov V.V. Russ. Chem. Bull. 46 (1997) 532
40. Bakalska R.I., and Chervenkova V.B. Bulg. Chem. Ind. 73 (2002) 108
41. crysalis red, Version 1.171.32.11, Oxford Diffraction Ltd.
42. Sheldrick, G. M.; Acta Crystallogr., Sect. A. 2008, 64, 112.
43. Flack H.D. Acta Crystallogr., Sect. A 39 (1983) 876
44. Ivanova B.B., Arnaudov M.G., and Bontchev P.R. Spectrochim. Acta, Part A 60 (2004) 855
45. Ivanova B.B., Tsalev D.L., and Arnaudov M.G. Talanta 69 (2006) 822
46. Ivanova B., Simeonov V., Arnaudov M., and Tsalev D. Spectrochim. Acta, Part A 67 (2007) 66
47. Koleva, B. B.; Kolev, T. M.; Simeonov, V.; Spassov, T.; Spiteller, M. J. Inclus. Prenome. 2008. doi:10.1007/s10847-008-9425-5.
48. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, Ö.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Salvador, P.; Dannenberg, J. J.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komáromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. gaussian 98, Gaussian: Pittsburgh, PA, 1998.
49. 'dalton', a molecular electronic structure program, Release 2.0, 2005, http://www.kjemi.uio.no/software/dalton/dalton.html.
50. Zhurko, G. A.; Zhurko, D. A. ChemCraft: Tool for treatment of chemical data, Lite version build 08, 2005.