Synthesis and diuretic activity of 2,3-dihydro-4(1h)-quinolinone 4- oxime-O-sulfonic acid derivatives

European Journal of Medicinal Chemistry

Volumn 33, Issue 4, 1998, Pages 267-277

  Nishijima, Kazumi ^a   Shinkawa, Tomoaki ^a   Yamashita, Yoshiaki ^a   Sato, Naofumi ^a   Nishida, Hidemitsu ^a   Kato, Kazuo ^a   Onuki, Yoshiaki ^a   Mizota, Masahiro ^a   Ohtomo, Kikuo ^b   Miyano, Soutarou ^c  

^a MOCHIDA PHARMACEUTICAL CO   (Japan)

^b Hodogaya Chemical Co   (Japan)

^c TOHOKU UNIVERSITY   (Japan)

Author keywords

Diuretic activity; Electrostatic potential map; Quinolinone oxime O sulfonic acid; Stereochemistry of oxime; Structure activity relationship

Indexed keywords

6 CHLORO 1,2,3,4 TETRAHYDRO 1 PROPIONYL 4 QUINOLINONE 4 OXIME; 7 CHLORO 2,3 DIHYDRO 1 (2 METHYLBENZOYL) 4(1H) QUINOLINONE 4 OXIME O SULFONIC ACID POTASSIUM; BUMETANIDE; FUROSEMIDE; M 17000; SULFONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CRYSTAL STRUCTURE; DERIVATIZATION; DIURESIS; DOG; DRUG EFFECT; DRUG SYNTHESIS; NONHUMAN; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

EID: 0032051763     PISSN: 02235234     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0223-5234(98)80061-5     Document Type: Article

References (26)

1. [1] Ohnishi H., Yamaguchi K., Takada K., Toyonaka Y., Suzuki Y., Orita Y., Drugs Exp. Clin. Re.s. 7 (1981) 823-832.
2. [2] Shinkawa T., Nakajima H., Nishijima K., Yamasaki F., Kato K., Ohzawa N., Mizota M., Eur. J. Pharmacol. 219 (1992) 217-224.
3. [3] Cragoe E.J. (Ed.), Chemistry and Pharmacology of Drugs, Vol. 2: Diuretics: Chemistry, Pharmacology and Medicine, Wiley, New York, 1983.
4. [4] Puschett J.B., Greenberg A. (Eds.), Diuretics: Chemistry, Pharmacology and Clinical Applications, Elsevier, New York, 1984.
5. [5] Shinkawa T., Yamasaki F., Kikuchi A., Nakakuki M., Nishijima K., Uemura A., Mizota M., Orita Y., Arzneim. Forsch. Drug Res. 42 (1992) 1466-1472.
6. [6] Shinkawa T., Yamasaki F., Notsu T., Nakakuki M., Nishijima K., Yoshitomi K., Imai M., Eur. J. Pharmacol. 238 (1993) 317-325.
7. [7] Elderfield R.C., Maggiolo A.D., J. Am. Chem. Soc. 71 (1949) 1906-1911.
8. [8] Smith P.A.S., J. Am. Chem. Soc. 70 (1948) 323-326.
9. [9] Burmistrov S.I., Taranenko A.G., Ukrain. Khim. Zhur. 22 (1956) 620-622; Chem. Abstr. 51 (1957) 5726.
10. [9] Burmistrov S.I., Taranenko A.G., Ukrain. Khim. Zhur. 22 (1956) 620-622; Chem. Abstr. 51 (1957) 5726.
11. [10] Ferrarini P.L., Mori C., Primofiore G., Da Settimo A., Breschi M.C., Martinotti E., Nieri P., Ciucci M.A., Eur. J. Med. Chem. 25 (1990) 489-496.
12. [11] Johnson W.S., Woroch E.L., Buell B.G., J. Am. Chem. Soc. 71 (1949) 1901-1905.
13. [12] Robert J., Julien W., Bernard G., Fr. Patent 1514280, 1968; Chem. Abstr. 70 (1969) 68195t.
14. [12] Robert J., Julien W., Bernard G., Fr. Patent 1514280, 1968; Chem. Abstr. 70 (1969) 68195t.
15. [13] Bradley G., Clark J., Kernick W., J. Chem. Soc. Perkin Trans. I (1972) 2019-2023.
16. [14] Kano S., Ebata T., Shibata S., J. Chem. Soc. Perkin Trans. I (1980) 2105-2111.
17. [15] Collins R.F., J. Chem. Soc. (1960) 2053-2059.
18. [16] Schlatter E., Greger R., Weidtke C., Pflugers Arch. 396 (1983) 210-217.
19. [17] Haas M., McManus T.J., Am. J. Physiol. 245 (1983) C235-C240.
20. [18] Giesen-Crouse E., Fandeleur P., Welsch C., Englert H., Lang H.J., Schmidt M., Imbs J.L., Fundam. Clin. Pharmacol. 2 (1988) 145-157.
21. [19] Hatano M. (Ed.), Nephrology, Vol. 2, Springer, Tokyo, 1991.
22. [20] Witter M., Di Stefano A., Wangemann P., Greger R., Drugs (1991; Suppl. 3) 1-13.
23. [21] Yasoshima K., Yamasaki F., Shinkawa T., Yoshitomi K., Imai M., J. Pharmacol. Exp. Ther. 266 (1993) 1581-1588.
24. [22] Yamasaki F., Yoshitomi K., Shinkawa T., Imai M., J. Pharmacol. Exp. Ther. 266 (1993) 1589-1593.
25. [23] TEXSAN: TEXRAY Structure Analysis Package, Molecular Structure Corporation, 1985.
26. [24] Johnson C.K., ORTEP 2, Report ORNL-5138, Oak Ridge National Laboratory, Oak Ridge, TN, 1976.