Synthesis and chemiluminescence of 1,3-disubstituted 4-hydroxypyrazolo[4′,3′:5,6]pyrido[2,3-d]pyridazine-5,8(6H,7H)- diones

Heterocycles

Volumn 44, Issue 1, 1997, Pages 85-88

  Tominaga, Yoshinori ^a   Yoshioka, Noriko ^a   Minematsu, Hiroki ^a   Kataoka, Seigo ^a  

^a NAGASAKI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000776440     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-96-S17     Document Type: Article

References (24)

1. H. O. Albrecht, Z. Phys. Chem., 1928, 136, 321.
2. a) "Bioluminescence and Chemiluminesence'" eds by A. K. Campbell, L. J. Kricka, and P. E. Stanley, John Wiley & Sons, Chichester, 1994, and references cited therein.
3. b) D. C. Young, S. D. Ryan, and F. J. Dutko, Anal. Biochem., 1993, 215, 24;
4. c). J. A. Matthews, A. Batki, C. Hynds, and L. J. Kricka, Anal. Biochem., 1985, 151, 205;
5. d) M. P. Wymann, von V. Tscharner, D. A. Deraulean, and M. Baggiolini, Anal. Biochem., 1987, 165, 371;
6. e) R. Lock, A. Johansson, K. Orselius, and C. Dahlgren, Anal. Biochem., 1988, 173, 450;
7. f) H. P. Misra and P. M. Squatrito, Arch Biochem. Biophys., 1982, 215, 59;
8. g) J. Arnhold, S. Mueller, K. Arnold, and K. Sonntag, J. Biolumin. Chemilumin., 1991, 6, 189;
9. h) G. Merenyi J. Lind, and T. E. Eriksen, J. Biolumin. Chemilumin., 1990, 5, 53;
10. M. Ii, H. Yoshida, Y. Araki, H. Masuya, T. Hada, M. Terada, M. Hatanaka, and Y. Ichimori, Biochem. Biophys. Res. Commun., 1993, 193, 540.
11. Y. Tominaga, N. Yoshioka, S. Kataoka, N. Aoyama, T. Masunari, and A. Miike, Tetrahedron Lett., 1995, 36, 8641.
12. Y. Ohkura, M. Kai, and T. Kumada, Bunseki Kagaku, 1994, 43, 259, and references cited therein.
13. Y. Tominaga, J.-K. Luo, L. W. Castle, and R. N. Castle, J. Heterocycl. Chem., 1993, 30, 267.
14. 1a: This compound was prepared by reaction of ethyl ethoxymethylenecyanoacetate with p-toluenesulfonylhydrazide under reflux in methanol in 77% yield, mp 151-152°C.
15. 1b: This compound was prepared from methyl bis(methylthio)methylenecyanoacetate and p-toluenesulfonylhydrazide in the same manner as the preparation for 1a in 73% yield, mp 155-156°C, colorless prisms.
16. 1c: R. Gompper and W. Topfl, Chem. Ber., 1962, 95, 2881.
17. 1 d: L. Bauer and C. S. Mahajanshetti, J. Heterocyl. Chem., 1967, 4, 325.
18. ++1). cf. H. Matsunaga, M. Sonoda, Y. Tomioka, and M. Yamazaki, Chem. Pharm. Bull., 1984, 32, 2596.
19. Commercially available from Tokyo Kasei.
20. 3)δ: 2.88(3H, s, SMe), 3.05(6H, s, NMe), 3.90(6H, s, OMe). cf. M. Sone, Y. Tominaga, R. Natsuki, Y. Matsuda, and G. Kobayashi, Chem. Pharm. Bull., 1973, 21, 1667.
21. 2), 5.60(1H, s, 4-H), 7.30-7.56(5H, m, phenyl-H).
22. +, 100), 308(46), 77(10).
23. CL intensity was measured with a Magic Lite Analyzer of CIBA-CORNING. CL spectrum was measured with the spectrofluorometer, Shimadzu RF-510.
24. Maximum wavelength in chemiluminescent spectrum of 3d was about 420 nm in the presence of 0.01 ml 4N NaOH solution and 0.01 mg/ml(290 μM) 3d in dimethyl sulfoxide.