Synthesis and hypolipidemic activity of N-substituted phthalimides. Part V

Farmaco

Volumn 58, Issue 12, 2003, Pages 1283-1288

  Sena, Vera L M ^a   Srivastava, Rajendra M ^a   Silva, Ricardo O ^a   Lima, Vera L M ^a  

^a FEDERAL UNIVERSITY OF PERNAMBUCO   (Brazil)

Author keywords

Cholesterol; Hypolipidemic activity; N Arylphthalimides; Triglycerides

Indexed keywords

2 (1,2,4 TRIAZOL 3 YL)ISOINDOLE 1,3 DIONE; 2 (2 CHLOROPHENYL)ISOINDOLE 1,3 DIONE; 2 (2 FLUOROPHENYL)ISOINDOLE 1,3 DIONE; 2 (3 CHLOROPHENYL)ISOINDOLE 1,3 DIONE; 2 (3 FLUOROPHENYL)ISOINDOLE 1,3 DIONE; 2 (4 CHLOROPHENYL)ISOINDOLE 1,3 DIONE; 2 (4 FLUOROPHENYL)ISOINDOLE 1,3 DIONE; 2 PHENYLISOINDOLE 1,3 DIONE; 2 [1H 1,2,4 TRIAZOL 3 YL]ISOINDOLE 1,3 DIONE; ANTILIPEMIC AGENT; CHOLESTEROL; PHTHALIMIDE DERIVATIVE; TRIACYLGLYCEROL; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ARTICLE; CHOLESTEROL BLOOD LEVEL; CONTROLLED STUDY; DRUG ACTIVITY; DRUG SYNTHESIS; MOUSE; NONHUMAN; TRIACYLGLYCEROL BLOOD LEVEL;

EID: 0242636463     PISSN: 0014827X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0014-827X(03)00185-X     Document Type: Article

References (25)

1. Lima L.M., Castro P., Machado A.L., Fraga C.A.M., Lugnier C., Moraes V.L.G., Barreiro E.J. Bioorg. Med. Chem. 10:2002;3067-3073.
2. Orzeszko A., Kaminska B., Orzesko G., Starosciak J. Synthesis and antimicrobial activity of new adamantine derivatives. II. Farmaco. 55:2000;619-623.
3. Chapman J.M. Jr., Cocolas G.H., Hall I.H. Hypolipidemic activity of phthalimide derivatives. 1. N-substituted phthalimide derivatives. J. Med. Chem. 22:1979;1399-1402.
4. Hall I.H., Chapman J.M. Jr., Cocolas G.H. Effects of imide analogs on enzymes required for cholesterol and fatty acid synthesis. J. Pharm. Sci. 70:1981;321-328.
5. Chapman J.M. Jr., Voorstad P.J., Cocolas G.H., Hall I.H. Hypolipidemic activity of phthalimide derivatives. 2. N-Phenylphthalimide and derivatives. J. Med. Chem. 26:1983;237-243.
6. Murthy A.R., Wong O.T., Reynolds D.J., Hall I.H. Synthesis and hypolipidemic activity of 3-imino-1-oxoisoindolines in rodents. Pharm. Res. 4:1987;21-27.
7. Ramos M.N., Neto B.d.B. Eletronic structure and hypolipidemic activity of phthalimide and related compounds: a QSAR study. J. Comput. Chem. 11:1990;572-596.
8. Neto M.D.C., Filho W.C.P., Neto B.B. The hypolipidemic activity of N-phenylphthalimide derivatives: a QSAR study. J. Braz. Chem. Soc. 4:1993;139-142.
9. Antunes R., Srivastava R.M. A new series of N-(3-phenyl-1,2,4-oxadiazol- 5-yl)alkylphthalimides. I. Heterocycl. Commun. 2:1996;247-250.
10. Srivastava R.M., Oliveira F.J.S., Silva L.P., de Freitas Filho J.R., Oliveira S.P., Lima V.L.M. Synthesis and hypolipidemic activity of N-phthalimidomethyl tetra-O-acyl-α-D-mannopyranosides. Carbohydr. Res. 332:2001;335-340.
11. Sena V.L.M., Srivastava R.M., Oliveira S.P., Lima V.L.M. Microwave-assisted synthesis of N-arylphthalamic acids with hyperlipidemic activity. Bioorg. Med. Chem. Lett. 11:2001;2671-2674.
12. M.S. Khajavi, F. Nikpour, M. Hajihadi, Microwave irradiation promoted reactions of anhydrides with isocyanates. Preparation of N-substituted phthalimides, J. Chem. Res. (S) (1996) 96-97.
13. Khalil A.M., Abdelgawad I.I., El-Metwally M.H. Synthesis of 2-aryl and 2-alkylthio-4-phthalyl-2-thiazolin-5-ones and their reactions with aromatic amines. Indian J. Chem. 51:1977;1029-1031.
14. Fahmy A.F.M., Aly N.F., Arief M.H. Phathalimides: part II - synthesis and reactions of N-(arylcarbamoyloxy)phthalimides. Indian J. Chem. 16B:1978;697-701.
15. Fahmy A.F.M., Aly N.F., Orabi M.O. Phthalimides. III. Ammonolysis, hydrazinolysis, pyrolysis and action of Grignard reagents on phthalimide derivatives. Bull. Chem. Soc. Jpn. 51:1978;2148-2152.
16. Pagani G., Buruffine A.J., Borgana P., Carcialanza G. Acidi ftalamici variamente N-sostituiti. Farmaco. 23:1968;448-457.
17. Suzuki K., Weisburger E.K., Weisburger J.H. Derivatives of 3-fluorofluorene by the Pschorr synthesis. J. Org. Chem. 26:1961;2239-2273.
18. Allain C.C., Poon L.S., Chan C.S., Richmond W., Fu P.C. Enzymatic determination of serum cholesterol. Clin. Chem. 20:1974;470-475.
19. McGrowan M.W., Artiss J.D., Strandberg D.R., Zak B. A peroxidase-coupled method for the colorimetric determination of serum triglycerides. Clin. Chem. 29:1983;538-542.
20. Demnitz J., Monteiro B.D.A., Mozart N.R., Srivastava R.M. Synthesis and mass spectral studies of N-arylphthalimides. Heterocycl. Commun. 3:1997;115-122.
21. Kanyonyo M.R., Poupaert J.H., Levêque P., Gozzo A., Van derpoorten K., Lambert D.M., Diouf O., Vamecq J. Reaction of aryl isothiocyanates with phthalic acid derivatives. Bull. Soc. Chim. Belg. 105:1996;55-56.
22. Fayat C., Foucaud A. Fréquences ét intensités des bands d'absorption infrarouge des vibrations de valence des carbonyls. II. N-phénylphthalimides. Problènie de la résonance de Fermi. Bull. Soc. Chim. France. 5:1970;4501-4505.
23. Gawronski J., Kazmierczak F., Gawronska K., Rychlewska U., Nordén B., Holmén A. Excited states of the phthalimide chromophore and their exciton couplings: a tool for stereochemical assignments. J. Am. Chem. Soc. 120:1998;2083-12091.
24. Lamb R.G., Wyrick S.D., Piantadosi C. Hypolipidemic activity of in vitro inhibitors of hepatic and intestinal sn-glycerol-3-phosphate acyltransferase and phosphatidate phosphohydrolase. Atherosclerosis. 27:1977;147-154.
25. R. Antunes, H. Batista, R.M. Srivastava, G. Thomas, C.C. Araújo, R.L. Longo, H. Magalhães, M.B.C. Leão, A.C. Pavão, Synthesis, characterization and interaction mechanism of new oxadiazolo-phthalimides as peripheral analgesics. IV, J. Mol. Struct., in press.