Synthesis of polycyclic pyridazinediones as chemiluminescent compounds

Journal of Heterocyclic Chemistry

Volumn 35, Issue 5, 1998, Pages 1219-1234

  Tominaga, Yoshinori ^a,c   Sasaki, Kenji ^b   Castle, Raymond N ^a  

^a NAGASAKI UNIVERSITY   (Japan)

^b OKAYAMA UNIVERSITY   (Japan)

^c UNIVERSITY OF SOUTH FLORIDA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001095683     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570350516     Document Type: Article

References (49)

1. W. J. Coates, Pyridazines and their Benzo Derivatives in Comprehensive Heterocyclic Chemistry II, Vol. 6, A. R. Katrizky, C. W. Rees and E. F. V. Scriven, eds, Pergamon Press, Oxford, 1993, p 1-91.
2. [2a] Y. Tominaga, N. Yoshioka, S. Kataoka, N. Aoyama, T. Masunari and A. Miike, Tetrahedron Leiters, 36, 8641 (1995);
3. [b] Y. Tominaga, N. Yoshioka and S. Kataoka, Heterocycles, 43, 1597 (1996);
4. Y. Tominaga, N. Yoshioka, H. Minematsu and S. Kataoka, Heterocycles, 44, 85 (1977);
5. Y. Tominaga, N. Yoshioka, S. Kataoka, Y. Shigemitsu, T. Hirota and K. Sasaki, Heterocycles, in press;
6. [e] Y. Tominaga, K. Komiya, S. Kataoka and Y. Shigemitsu, Heterocycles, in press.
7. [3a] T. O. Burdo and W. Rudolf Seitz, Anal. Chem., 47, 1639 (1975);
8. [b] R. B. Brundrett, D. F. Roswell and E. H. White, J. Am. Chem. Soc., 94, 7536 (1972);
9. C. C. Wei and E. H. White, Tetrahedron Letters, 39, 3559 (1971);
10. M. Ii, H. Yoshida, Y. Aramaki, H. Masuya, T. Hada, M. Terada, M. Hatanaka and Y. Ichimori, Kochern. Biophy. Res. Commun., 193, 540 (1993).
11. H. O. Albrecht, Z. Phys. Chem., 136, 321 (1928).
12. Bioluminescence and Chemiluminesence, A. K. Campbell, L. J. Kricka and P. E. Stanley, eds, John Wiley & Sons, Chichester, 1994 and 1996, and references cited therein.
13. [6a] D. C. Young, S. D. Ryan and F. J. Dutko, Anal. Biochem., 215, 24 (1993);
14. [b] J. A. Matthews, A. Batki, C. Hynds and L. J. Kricka, Anal. Biochem., 151, 205 (1985);
15. M. P. Wymann, von V. Tscharner, D. A. Deraulean and M. Baggiolini, Anal. Biochem., 165, 371 (1987);
16. R. Lock, A. Johansson, K. Orselius and C. Dahlgren, Anal. Biochem., 173, 450 (1988);
17. [e] H. P. Misra and P. M. Squatrito, Arch Biochem. Biophys, 215, 59 (1982);
18. [f] J. Arnhold, S. Mueller, K. Arnold and K. Sonntag, J. Biolumin. Chemilumin., 6, 189 (1991);
19. [g] G. Merenyi, J. Lind and T. E. Eriksen, J. Biolumin. Chemilumin., 5, 53 (1990).
20. Y. Tominaga, J.-K. Luo, L. W. Castle and R. N. Castle, J. Heterocyclic Chem., 30, 267 (1993).
21. M. li, H. Yoshida, Y. Araki, H. Masuya, T. Hada, M. Terada, M. Hatanaka and Y. Ichimori, Biochem. Biophys. Res. Commun., 193, 540 (1993).
22. [9a] E. C. Taylor and A. McKillop, The Chemistry of Cyclic Enaminonitriles and o-Aminonitriles, Interscience, New York, 1970;
23. [b] Y. Tominaga, S. Kohra, H. Honkawa and A. Hosomi, Heterocycles, 29, 1409 (1989);
24. Y. Tominaga, Trends in Heterocyclic Chemistry, J. Menon, ed, Council of Scientific Research Integration, Research Trends, 2, 43 (1991).
25. Y. Ohkura, M. Kai and T. Kumada, Bunseki Kagaku, 43, 259 (1994), and references cited therein.
26. 8b: This compound was prepared from methyl bis(methylthio)methylenecyanoacetate and p-toluenesulfonylhydrazide in the same manner as the preparation for Sa in 73% yield, mp 155-156°, colorless prisms.
27. 8c: R. Gompper and W. Topfl, Chem. Ber., 95, 2881 (1962).
28. 8d: L. Bauer and C, S. Mahajanshetti, J. Heterocyclic Chem., 4, 325 (1967).
29. Commercially available from Tokyo Kasei.
30. 1H-nmr (deuteriochloroform): 8 2.88 (3H, s, SMe), 3.05 (6H, s, NMe), 3.90 (6H, s, OMe);
31. cf. M. Sone, Y. Tominaga, R. Natsuki, Y. Matsuda and G. Kobayashi, Chem. Pharm. Bull., 21, 1667 (1973).
32. 2), 5.60 (1H, s, 4-H), 7.30-7.56 (5H, m, phenyl-H).
33. [17a] Y. Tominaga, Trends Heterocyclic Chem., 2, 43 (1991);
34. [b] Y. Tominaga, S. Kohra, H. Honkawa and A. Hosomi, Heterocycles, 29, 1409 (1989);
35. R. K. Dieter, Tetrahedron, 42, 3029 (1986);
36. H. Junjappa, H. lia and C. V. Asoka, Tetrahedron, 46, 5423 (1990);
37. [e] M. Kolb, Synthesis, 171 (1990);
38. [f] W. J. Middleton and V. A. Engelhardt, J. Am. Chem. Soc., 80, 2829 (1958);
39. [g] Y. Tominaga, S. Kohra, H. Honkawa and H. Hosomi, Heterocycles, 29, 1409 (1989).
40. [18a] M. Sone, Y. Tominaga, R. Natsuki, Y. Matsuda and G. Kobayashi, Yakugaku Zasshi, 93, 1008 (1973);
41. [b] M. Sone, Y. Tominaga, R. Natsuki, Y. Matsuda and G. Kobayashi, Chem. Pharm. Bull., 21, 1667 (1973).
42. [19a] W. Flitsch, Bicyclic 5-6 System with One Ring Junction Nitrogen Atom: No Extra Heteroatom in Comprehensive Heterocyclic Chemistry II, Vol. 8, by A. R. Katrizky, C. W. Rees and E. F. V. Scriven, eds, Pergamon Press, Oxford, 1993, p 237;
43. [b] W. Flitsch, Pyrroles with Fused Six-membered Heterocyclic Rings: (i) a-Fused, in Comprehensive Heterocyclic Chemistry, 1st edn, Vol 4, A. R. Katrizky, C. W. Rees and E. F. V. Scriven, eds, Pergamon Press, Oxford, 1984, p 443;
44. Y. Tominaga, Y. Shiroshila and A. Hosomi, Helerocycles, 27, 2251 (1988).
45. [20a] R. G. Gould and W. A. Jacobs, J. Am. Chem. Soc., 61, 2890 (1939);
46. [b] Y. Tominaga, T. Michioka, K. Moriyamaand A. Hosomi, J. Heterocyclic Chem., 27, 1217 (1990).
47. 31: This compound was prepared along with ethyl 7-dimethy]amino-l-nitro-2-methylthioindolizine-3-carboxylate by reaction of 1-ethoxycarbonylmethylpyridinium bromide with l, l-bis(methylthio)-2-nitroethylene in the presence of potassium carbonate in dimethyl sulfoxide; cf. Y. Matsuda, K. Katou, H. Matsumoto, S. Ide, K. Takahashi, K. Torisu, K. Furuno and S. Maeda, Yakugaku Zasshi, 42, 112 (1992).
48. Chemiluminescence Measurements: Method A: Reaction solutions (1 ml) containing 0.1 mg/ml of Luminol and each compound, lU/ml horseradish peroxidase, 0.5 mg/ml Triton X-100 in 20 mW Phosphate buffer pH 8.0 were prepared. Each 400 μl reaction solution in a glass tube was incubated 10 minutes at 37°, and into which a luminometer, was immediatly placed, maintaining the system at 37°. Photons were counted for 1 minute after addition of 10 μl of 90 mAf of hydrogen peroxide and 10 μl of l.OAf sodium hydroxide. In the case of the measurement of hydrogen peroxide and horseradish peroxidase as shown in Figures 3 and 4, photons were counted for 1 minute after addition of each 10 μl of various concentration of hydrogen peroxide and horseradish peroxidase (Table 3, Figures 3 and 4).
49. Method B: A reaction solution was prepared with a 10 rnAf phosphate buffer solution (pH 6, 7, 8 or 10) containing a 0.5 ml/1 of Triton X-100, various concentration of substrate dissolved in dimethyl sulfoxide and 5000 units/1 of arthromyces ramosus peroxidase. A 3.0 ml of reaction solution was introduced into a Brosilicate Glass tube which was then incubated at 37° for 10 minutes. At the end of the incubation period, the sample tube to be counted was set into a chemiluminescence counter. The chemiluminescence reaction was initiated by injecting 0.3 ml of various concentrations of hydrogen peroxide solution. Photons were counted for 1 or 10 seconds from the start of the reaction. The chemiluminescence measurements were perfomed with a Magic analyzer (CIBA Corning Co. Ltd., USA). All of the reagent concentrations shown in the figure captions are the final values (Figures 5, 6, 7, 9 and Tables 4, 5 and 6).