Preparation of 5,5′-pyrilidene and 5,5′-quinolidene bis-barbituric acid derivatives

Journal of Heterocyclic Chemistry

Volumn 40, Issue 3, 2003, Pages 465-474

  Jursic, Branko S ^a   Neumann, Donna M ^a  

^a UNIVERSITY OF NEW ORLEANS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

5,5' PYRILIDENEDIBARBITURIC ACID; 5,5' QUINOLIDENEDIBARBITURIC ACID; ALDEHYDE; BARBITURIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; ELECTRON TRANSPORT; NUCLEAR MAGNETIC RESONANCE; POLYMERIZATION; PROTON TRANSPORT; STRUCTURE ACTIVITY RELATION;

EID: 0038298271     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570400310     Document Type: Article

References (22)

1. [a] T. F. Kresina, Editor "Immune-Modulating Agents" Deker, New York, N. Y. (1998);
2. [b] G. G. Gomez, R. B. Hutchison and C. A. Kruse, Cancer Treat. Rev., 27, 375 (2001);
3. [c] F. Lori, AIDS (London), 13, 1433 (1999);
4. [d] H. Baba, T. Kunimoto, K. Nitta, K. Sato, S. Hashimoto, M. Kohno, Y. Kita and H. Ogawa, Int. J. Immunopharmacol., 8, 569 (1986).
5. [a] I. Watanabe, T. Andoh, R. Furuya, T. Sasaki, Y. Kamiya and H. Itoh, Anesthesia & Analgesia (Baltimore), 88, 1406 (1999);
6. [b] J. M. Gonzales, J. Neurochem., 64, 2559 (1995);
7. [c] K. Hirota, M. Kudo, T. Kudo, M. Kitayama, T. Kushikata, D. G. Lambert and A. Matsuki, Neuroscience Lett., 291, 175 (2000);
8. [d] P. R. Andrews, G. P. Jones and D. B. Poulton, Eur. J. Pharmacol., 79, 61 (1982);
9. [e] G. B. Young, W. T. Blume, C. F. Bolton and K. G. Warren, Can. J. Neurological Sciences, 7, 291 (1980).
10. [a] T. R. Bailey and D. C. Young, International Patent WO 13708 (2000); Chem. Abstr., 132, 203127 (2000);
11. [b] R. I. Ashkinazi, International Patent WO 25699 (1999); Chem. Abstr., 131, 5267 (1999);
12. [c] L. R. Morgan, B. S. Jursic, C. L. Hooper, D. M. Neumann, K. Thangaraj and B. LeBlanc, Bioorg. Med. Chem. Lett., 12, 3407 (2002).
13. For instance see B. S. Jursic, J. Heterocyclic Chem., 38, 655 (2001), and references therein.
14. B. S. Jursic, D. M. Neumann, Z. Moore and E. D. Stevens, J. Org. Chem., 67, 2372 (2002).
15. B. S. Jursic, J. Heterocyclic Chem., 00, 0000 (2003).
16. For reviews of Michael reactions see: [a] E. D. Bergmann, D. Ginsburg and R. Pappo, Org. React., 10, 179 (1959); [b] L. A. Yanovskaya, G. V. Kryshtal and V. V. Kulganek, Russ. Chem. Rev., 53, 744 (1984).
17. For reviews of Michael reactions see: [a] E. D. Bergmann, D. Ginsburg and R. Pappo, Org. React., 10, 179 (1959); [b] L. A. Yanovskaya, G. V. Kryshtal and V. V. Kulganek, Russ. Chem. Rev., 53, 744 (1984).
18. 3 forms. For more information see: T. H. Lowry and K. S. Richardson "Mechanism and Theory in Organic Chemistry" Third Edition, Harper & Row, Publishers, New York, N.Y. 1987 and references therein
19. [a] A. R. Katritzky, "Handbook of Heterocyclic Chemistry" Pergamon Press, New York, N. Y. 1985;
20. [b] D. L. Comins,) and S. Connor, Adv. Heterocycl. Chem., 44, 199 (1988);
21. [c] G. A. Olah, J. A. Olah and N. A. Overchuk, J. Org. Chem., 30, 3373 (1965).
22. Positive electro-spray studies in diluted acetic acid and diluted methanol are underway to fully characterize mechanism and intermediates in diaromaticdialdehydes with substituted barbituric acid. These experiments in conjunction with NMR spectroscopic studies will provide close insight into the nature of tetra-barbituric acid adducts of potential immuno-modulating agents.