Synthesis, structural investigations and biological evaluation of novel hexahydropyridazine-1-carboximidamides, -carbothioamides and -carbothioimidic acid esters as inducible nitric oxide synthase inhibitors

Bioorganic and Medicinal Chemistry

Volumn 12, Issue 5, 2004, Pages 1071-1089

  Morgenstern, Olaf ^a   Wanka, Heike ^a   Röser, Ilka ^a   Steveling, Antje ^a   Kuttler, Beate ^a  

^a UNIVERSITY OF GREIFSWALD   (Germany)

Author keywords

Aminoguanidine; Hexahydropyridazine 1 carboximidamides; Inducible nitric oxide synthase; Rat insulinoma cells (RIN)

Indexed keywords

AMINOGUANIDINE; GAMMA INTERFERON; INDUCIBLE NITRIC OXIDE SYNTHASE; INSULIN; INTERLEUKIN 1; NITRIC OXIDE; NITRIC OXIDE SYNTHASE INHIBITOR; NITROGEN; PYRIDAZINE DERIVATIVE;

ANIMAL CELL; ARTICLE; ATOM; CELL STRAIN; CELL SURVIVAL; CONTROLLED STUDY; DRUG EFFECT; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVITY; ENZYME INHIBITION; EVALUATION; IC 50; NONHUMAN; RAT; STANDARDIZATION; STRUCTURE ACTIVITY RELATION;

EID: 1342279559     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2003.12.007     Document Type: Article

References (75)

1. Moncada S., Higgs A.N. Engl. J. Med. 329:1993;2002.
2. Lowenstein C.L., Dinerman J.L., Snyder S.H. Ann. Intern. Med. 120:1994;227.
3. Michel T., Feron O. J. Clin. Invest. 100:1997;2146.
4. Nathan C.F. Cell. 82:1995;873.
5. Liu B., Gao H.M., Wang J.Y., Jeohn G.H., Cooper C.L. Ann. N.Y. Acad. Sci. 962:2002;318.
6. Hon W.M., Lee K.H., Khoo H.E. Ann. N.Y. Acad. Sci. 962:2002;275.
7. Abrason S.B., Amin A.R., Clancy R.M., Attur M. Best. Pract. Res. Rheumatol. 15:2001;831.
8. Bernadeau C., Dernis-Labous E., Blanchard H., Lamarque D., Breban M. Joint Bone Spine. 68:2001;457.
9. Nerup J., Mandrup-Poulsen T., Helquist S., Andersen H.U., Pociot F., Reimers J.I., Cuartero B.G., Karlsen A.E., Bjerre U., Lorenzen T. Diabetologia. 37:1994;82.
10. Sandler S., Eizirik D.L., Svensson C., Strandell E., Welsh M., Welsh N. Autoimmunity. 10:1991;241.
11. Rabinovitch A., Suarez-Pinzon W.L., Strynadka K., Schulz R., Lakey J.R., Warnock G.L., Rajotte R.V. J. Clin. Endicrinol. Metab. 79:1994;1058.
12. Eizirik D.L., Leijerstam F. Diabet. Metab. 20:1994;116.
13. Welsh N., Eizirik D.L., Bendtzen K., Sandler S. Endocrinology. 129:1991;3167.
14. Dean B.M., Walker R., Bare R.J., Baird J.D., Cook A. Diabetologia. 28:1985;464.
15. Spinas G.A., Laffranchi R., Francoys I., David I., Richter C., Reinecke M. Diabetologia. 41:1998;292.
16. Panagiotidis G., Akesson B., Alm P., Lundquist I. Endocrine. 2:1994;787.
17. Misko T.P., Moore W.M., Kasten T.P., Nickols G.A., Corbett J.A., Tilton R.G., McDaniel M.L., Williamson J.R., Currie M.G. Eur. J. Pharmacol. 233:1993;119.
18. Corbett J.A., McDaniel M.L. Diabetes. 41:1992;897.
19. Hao W., Myhre A.P., Palmer J.P. Autoimmunity. 29:1999;93.
20. Takamura T., Kato I., Kimura N., Nakazawa T., Yonekura H., Takasawa S., Okomoto H. J. Biol. Chem. 273:1998;2493.
21. Wu G. Diabetes. 44:1995;360.
22. Corbett J.A., Mikhael A., Shimizu J., Frederick K., Misko T.P., McDaniel M.L., Kanagawa O., Unanue E.R. Proc. Natl. Acad. Sci. U.S.A. 90:1993;8992.
23. Zhou X., Potoka D.A., Boyle P., Nadler E.P., McGinnis K., Ford H.R. FEBS Microbiol. Lett. 206:2002;93.
24. Holstad M., Jansson L., Sandler S. Biochem. Pharmacol. 51:1996;1711.
25. Holstad M., Sandler S. Autoimmunity. 15:1993;311.
26. Bryk R., Lubeskie A., Wolff D.J. Arch. Biochem. Biophys. 369:1999;243.
27. Wolff D.J., Lubeskie A. Arch. Biochem. Biophys. 316:1995;290.
28. Moore W.M., Webber R.K., Fok K.F., Jerome G.M., Connor J.R., Manning P.T., Wyatt P.S., Misko T.P., Tjoeng F.S., Currie M.G. J. Med. Chem. 39:1996;669.
29. Moore W.M., Webber R.K., Fok K.F., Jerome G.M., Kornmeier C.M., Tjoeng F.S., Currie M.G. Bioorg. Med. Chem. 4:1996;1559.
30. Watterson D.M., Mirzoeva S., Guo L., Whyte A., Bourguignon J.J., Hibert M., Haiech J., van Eldik L. J. Neurochem. Int. 39:2001;459.
31. Mirzoeva S., Sawkar A., Zasadzki M., Guo L., Velentza A.V., Dunlap V., Bourguignon J.J., Ramstrom H., Haiech J., van Eldik L.J., Watterson D.M. J. Med. Chem. 45:2002;563.
32. Alder K., Niklas H. Liebigs Ann. Chem. 585:1954;81.
33. Ohta H., Jikihara T., Wakabayashi K., Fujita T. Pestic. Biochem. Physiol. 14:1980;153.
34. Wakabayashi, O.; Ohta, H.; Jikihara, T.; Matsuya, K.; Suzuki, S. U.S. Patent 4,249,934, 1981; Chem. Abstr. 1981, 95, 62 219 y.
35. Nagano, E.; Hashimoto, S.; Yoshida, R.; Matsumoto, H.; Kamoshita, K. E.P. Patent 75,267, 1983; Chem. Abstr. 1983, 99, 194 984 m.
36. Ogino C., Hoshi T., Iida T., Koura S., Ogawa H., Kohno H., Sato Y., Takai M., Wakabayashi K. J. Pestic. Sci. (Int. Ed.). 18:1993;369.
37. Yamaguchi, M.; Watase, Y.; Kanbe, T.; Kato, S. J. P. Patent 62 00 091, 1987 [87 00 091]; Chem. Abstr. 1987, 107, 134316 u, E.P. Patent, 273,417, 1988; Chem. Abstr. 1988, 109, 211 069 m.
38. Chang, J. H. U.S. Patent, 4,830,659, 1989; Chem. Abstr. 1989, 111, 73 086 c.
39. Yamaguchi, M.; Suzuki, C.; Matsunari, K.; Miyazawa, T.; Nakamura, Y. E.P. Patent, 312,064, 1989; Chem. Abstr. 1989, 111, 35 142 k.
40. Chang, J. H. U.S. Patent 4,906,281, 1990, Chem. Abstr. 1990, 113, 23 927 y.
41. Chang, J. H. U.S. Patent 4,913,723, 1990, Chem. Abstr. 1990, 113, 132 204 f.
42. Rueb, L.; Eicken, K.; Westphalen, K.-O.; Würzer, B. D. E. Patent 3,927,388, 1991; Chem. Abstr. 1991, 115, 8 812 e.
43. Pissiotas, G.; Moser, H.; Brunner, H.-G. E.P. Patent 528,765, 1993; Chem. Abstr. 1993, 118, 234 076 m.
44. Pissiotas, G.; Moser, H.; Brunner, H.-G. E.P. Patent 611,768, 1994, Chem. Abstr. 1994, 121, 230 805 n.
45. Schallner, O.; Andree, R.; Drewes, M. W.; Dollinger, M.; Santel, H.-J. E.P. Patent 648,772, 1995; Chem. Abstr. 1995, 123, 9 454 s.
46. Hunter, W. T. U.S. Patent 2,841,584, 1958; Chem. Abstr. 1962, 56, 2 460.
47. Baranger P., Levisalles J. Bull. Soc. Chim. France. 1957;704.
48. Rink M., Mehta S., Grabowski K. Arch. Pharmaz. 292:1959;225.
49. Song J., Hesse M. Tetrahedron. 49:1993;6797.
50. De Waard E.R., Neeter R., Pandit U.K., Huisman H.O. Rec. Trav. Chem. Pays-Bas. 87:1968;572.
51. Dervan P.B., Santilli D.S. J. Am. Chem. Soc. 102:1980;3863.
52. Schildberg M., Debaerdemaeker T., Friedrichsen W. Chem. Ber. 121:1988;887.
53. Engelhardt U., Stromburg B. Phosphorus, Sulfur and Silica. 41:1989;235.
54. Yasumura, M.; Nakamura, S. J.P. Patent 08 198 853, 1996 [96 198 853]; Chem. Abstr. 1996, 125, 247 842 c.
55. Jung M.E., Lyster M.A. Chem. Comm. 1978;315.
56. Kamimura, S.; Nakamura, Y.; Tanazawa, H.; Ota, C.J.P. Patent 10 029 98, 1998 [98 029 981]; Chem. Abstr. 1998, 128, 154 092 e.
57. Groszkowski S., Wrona J., Szuflet W. Rocz. Chem. 47:1973;1551.
58. Groszkowski S., Wrona J. Pol. J. Pharmacol. Pharm. 30:1979;713.
59. Stetter H., Spangenberger H. Chem. Ber. 91:1958;1982.
60. Nakamura, T. W.O. Patent 92 12,136, 1992; Chem. Abstr. 1993, 118, 124 555 j.
61. Hasegawa, Y.; Hyoda, S.; Fujita, H.; Sawada, H.; Oki, Y. E.P. Patent 850,930, 199, Chem. Abstr. 1998, 129, 95 501 h.
62. Lüttringhaus A., Jander J., Schneider R. Chem. Ber. 92:1959;1756.
63. Stetter H., Woernle P. Liebigs Ann. Chem. 724:1969;150.
64. Marquis R. Compt. Rend. Acad. Sci. 136:1903;368.
65. Morgenstern O., Klemann A., Richter P.H. Pharmazie. 46:1991;505.
66. Rademacher P. Angew. Chem. 85:1973;410.
67. Rademacher P., Koopmann H. Chem. Ber. 108:1975;1557.
68. Dixon A.E., Taylor J. J. Chem. Soc. 101:1912;2502.
69. Wakabayashi, O.; Matsutani, H.; Ota, H.; Naohara, H.; Watanabe, H. J.P. Patent 52 113 961, 1977 [77 113 961]; Ref. Zh. Khim. 1978, 120, 346P.
70. Morgenstern O., Richter P.H., Klemann A. Pharmazie. 46:1991;418.
71. Munier R. Bull. Soc. Chim. Biol. 35:1953;1225.
72. Awe W. Pharmazie. 3:1948;492.
73. Suzuki H., Tsuji J., Hiroi Y., Sato N., Osuka A. Chem. Lett. 1983;449.
74. Gadzar A.F., Chick W.L., Oie H.K. Proc. Natl. Acad. Sci. U.S.A. 77:1980;3519.
75. Green L.C., Wagner D.A., Glogowski J., Skipper P.L., Wishnok J.S., Tannenbaum R.S. Anal. Biochem. 126:1982;131.