Synthesis and biological evaluation of several coumarin-4- carboxamidoxime and 3-(coumarin-4-yl)-1,2,4-oxadiazole derivatives

European Journal of Medicinal Chemistry

Volumn 33, Issue 9, 1998, Pages 715-724

  Nicolaides, Demetrios N ^a   Fylaktakidou, Konstantina C ^a   Litinas, Konstantinos E ^a   Hadjipavlou Litina, Dimitra ^a  

^a ARISTOTLE UNIVERSITY OF THESSALONIKI   (Greece)

Author keywords

3 (coumarin 4 yl) 1,2,4 oxadiazoles; Antiinflammatory; Antioxidants; Coumarin 4 carboxamidoximes; Coumarin 4 nitriloxides

Indexed keywords

2 OXO 2H 1 BENZOPYRAN 4 CARBOXAMIDE OXIME; 3 (2 OXO 2H 1 BENZOPYRAN 4 YL) 1,2,4 OXADIAZOLE; 5 ACETONYL 3 (2 OXO 2H 1 BENZOPYRAN 4 YL) 1,2,4 OXADIAZOLE; 5 METHYL 3 (2 OXO 2H 1 BENZOPYRAN 4 YL) 1,2,4 OXADIAZOLE; 5 PHENYL 3 (2 OXO 2H 1 BENZOPYRAN 4 YL) 1,2,4 OXADIAZOLE; 5 TRIFLUOROMETHYL 3 (2 OXO 2H 1 BENZOPYRAN 4 YL) 1,2,4 OXADIAZOLE; BETA GLUCURONIDASE; COUMARIN DERIVATIVE; LIPOXYGENASE; N (2' HYDROXYETHYL) 2 OXO 2H 1 BENZOPYRAN 4 CARBOXAMIDE OXIME; N (4' METHYLPHENYL) 2 OXO 2H 1 BENZOPYRAN 4 CARBOXAMIDE OXIME; N (DIMETHYLAMINO) 2 OXO 2H 1 BENZOPYRAN 4 CARBOXAMIDE OXIME; N (ETHOXYCARBONYLMETHYL) 2 OXO 2H 1 BENZOPYRAN 4 CARBOXAMIDE OXIME; N CYCLOHEXYL 2 OXO 2H 1 BENZOPYRAN 4 CARBOXAMIDE OXIME; N PHENYL 2 OXO 2H 1 BENZOPYRAN 4 CARBOXAMIDE OXIME; TRYPSIN; UNCLASSIFIED DRUG;

ANTIINFLAMMATORY ACTIVITY; ANTIOXIDANT ACTIVITY; ARTICLE; DRUG SYNTHESIS; ENZYME INHIBITION; OXIDATION REDUCTION POTENTIAL; PHYSICAL CHEMISTRY; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION;

EID: 0032413633     PISSN: 02235234     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0223-5234(98)80030-5     Document Type: Article

References (37)

1. [1] Murray R.D.H., Mendez I., Brawn S.A., The Natural Coumarins, Wiley, New York, 1982.
2. [2] Alka K., Vasant K.A., Rao M.N.A., Die Pharmazie 44 (1989) 870.
3. [3] Maddi V., Raghu K.S., Rao M.N.A., J. Pharmaceut. Sci. 81 (1992) 964-966.
4. [4] Larson R.A., Phytochemistry 27 (1988) 969-978.
5. [5] Mora A., Paya M., Rios J.L., Alcaraz M.J., Biochem. Pharmacol. 40 (1990) 793-797.
6. [6] Paya M., Halliwell B., Hoult J.R.S., Biochem. Pharmacol. 44 (1992) 205-214.
7. [7] Neichi T., Kashihara Y., Musota S.I., Biochim. Biophys. Acta 753 (1993) 130-132.
8. [8] Kimura Y., Okuda H., Arichi S., Baba K., Kozawa M., Biochim. Biophys. Acta 834 (1985) 224-229.
9. [9] Ozaki Y., Ohashi T., Niwa Y., Biochem. Pharmacol. 35 (1986) 3481-3488.
10. [10] Gharde A.D., Ghiya B.J., J. Indian Chem. Soc. 69 (1992) 397-398.
11. [11] Mazunder A., Wang S., Neamati N., Nicklams M., Sunder S., Chen J., Milne G.W.A., Rice W., Burke Jr. T., Pommier Y., J. Med. Chem. 39 (1996) 2472-2481.
12. [12] Litinas K.E., Nicolaides D.N., Varella E.A., J. Heterocycl. Chem. 27 (1990) 769-774.
13. [13] Nicolaides D.N., Bezergiannidou-Balouctsi C., Litinas K.E., Malamidou-Xenikaki E., Mentzafos D., Terzis A., J. Chem. Res. (S) (1993) 108-109; (M) (1993) 826-851.
14. [13] Nicolaides D.N., Bezergiannidou-Balouctsi C., Litinas K.E., Malamidou-Xenikaki E., Mentzafos D., Terzis A., J. Chem. Res. (S) (1993) 108-109; (M) (1993) 826-851.
15. [14] Nicolaides D.N., Bezergiannidou-Balouctsi C., Litinas K.E., Malamidou-Xenikaki E., Mentzafos D., Terzis A., Tetrahedron 49 (1993) 9127-9136.
16. [15] Bezergiannidou-Balouctsi C., Litinas K.E., Malamidou-Xenikaki E., Nicolaides D.N., Liebigs Ann. Chem. (1993) 1175-1177.
17. [16] Nicolaides D.N., Fylaktakidou K.C., Bezergiannidou-Balouctsi C., Litinas K.E., J. Heterocycl. Chem. 31 (1994) 173-176.
18. [17] Nicolaides D.N., Fylaktakidou K.C., Litinas K.E., Hadjipavlou-Litina D., J. Heterocycl. Chem. 33 (1996) 967-971.
19. [18] Nicolaides D.N., Fylaktakidou K.C., Litinas K.E., Papageorgiou G.K., Hadjipavlou-Litina D., J. Heterocycl. Chem. 35 (1998) 619-625.
20. [19] Nicolaides D.N., Fylaktakidou K.C., Litinas K.E., Hadjipavlou-Litina D., unpublished results.
21. 20] Nicolaides D.N., Varella E.A., The Chemistry of Amidoximes Suppl. B, In: Patai S. (Ed.), The Chemistry of Acid Derivatives, Vol. 2, Part 2, Wiley Interscience, New York, 1992, p. 875.
22. 21] Staunton J., In: Sammes P.G. (Ed.), Comprehensive Organic Chemistry, Vol. 4, Pergamon Press, Oxford, 1979, p. 648.
23. 22] Soliman A.Y., El-Nagdy S., Bakeer H.M., Moustafa M.M., Indian J. Chem. 29(B) (1990) 239-243.
24. 23] Bata I., Korbonits D., Kolonits P., Podanyi B., Takacsy-Eros T., Simon K., Chem. Ber. 126 (1993) 1835-1841.
25. 24] Berndt E.W., Fratzke H.A., Held B.G., J. Heterocycl. Chem. 9 (1972) 137-140.
26. 25] Kocevar M., Stanovnik B., Tisler M., J. Hetcrocycl. Chem. 19 (1982) 1397-1402.
27. 26] Yale H.L., Spitzmiller E.R., J. Heterocycl. Chem. 15 (1978) 1373-1378.
28. [27] Burakevich J.V., Butler R.S., Volpp G.P., J. Org. Chem. 37 (1972) 593-596.
29. [28] Sümengen D., Pelter A., J. Chem. Soc. Perkin Trans. I (1983) 687-691.
30. [29] Tandon M., Tandon P., Barthwhal J.P., Bhalla T.N., Bhagrava K.P., Arzneim. Forsch. Drug Res. 32 (1982) 1233-1235.
31. [30] Di Rosa M., Girroud J.P., Willougby D.A., J. Pathol. 104 (1971) 15-23.
32. [31] Taraborewala R.B., Kauffman J.M., J. Pharm. Sci. 79 (1990) 173-178.
33. [32] Blois M.S., Nature (London) 181 (1958) 1199.
34. [33] Hadjipavlou-Litina D., Res. Commun. Chem. Pathol. Pharmacol. 81 (1993) 1091-1102.
35. [34] Hadjipavlou-Litina D., Geronikaki A.A., Arzneim. Forsch. Drug. Res. 46 (1996) 805-808.
36. [35] Robak J., Gryglewski R.J., Biochem. Pharmacol. 37 (1988) 837-841.
37. [36] Rajakumar D.V., Rao M.N., Biochem. Pharmacol. 45 (1993) 2067-2072.