Synthesis and pharmacological evaluation of novel antinociceptive N-substituted-phenylimidazolyl-4-acylhydrazone derivatives

Farmaco

Volumn 57, Issue 12, 2002, Pages 999-1007

  Cunha, Anna C ^a   Tributino, Jorge L M ^a   Miranda, Ana L P ^a   Fraga, Carlos A M ^a   Barreiro, Eliezer J ^a  

^a FEDERAL UNIVERSITY OF RIO DE JANEIRO   (Brazil)

Author keywords

Analgesic activity; Antiinflammatory activity; N substituted phenylimidazolyl 4 acylhydrazone derivatives

Indexed keywords

2 METHYLIMIDAZOLYL 3 ACYLHYDRAZONE; HYDRAZONE DERIVATIVE; PHENYLIMIDAZOLYL 4 ACYLHYDRAZONE; UNCLASSIFIED DRUG; ANALGESIC AGENT; IMIDAZOLE DERIVATIVE; NONSTEROID ANTIINFLAMMATORY AGENT;

ANALGESIC ACTIVITY; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIINFLAMMATORY ACTIVITY; ANTINOCICEPTION; ARTICLE; CONTROLLED STUDY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; EVALUATION; FEMALE; MALE; MOLECULAR HYBRIDIZATION; MOUSE; NONHUMAN; RAT; ANIMAL; DISEASE MODEL; EDEMA; PAIN; SYNTHESIS;

ANALGESICS; ANIMALS; ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; DISEASE MODELS, ANIMAL; EDEMA; FEMALE; HYDRAZONES; IMIDAZOLES; MALE; MICE; PAIN; RATS;

EID: 0036903031     PISSN: 0014827X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0014-827X(02)01286-7     Document Type: Article

References (15)

1. Ribeiro I.G., Silva K.C.M., Parrini S., Miranda A.L.P., Fraga C.A.M., Barreiro E.J. Synthesis and antinociceptive properties of new structurally planned imidazo[1,2-a]pyridine 3-acylarylhydrazone derivatives. Eur. J. Med. Chem. 33:1998;225-235.
2. Todeschini A.R., Miranda A.L.P., Silva K.C.M., Parrini S.C., Barreiro E.J. Synthesis and evaluation of analgesic, antiinflammatory and antiplatelet properties of new 2-pyridylarylhydrazone derivates. Eur. J. Med. Chem. 33:1998;189-199.
3. Silveira I.A.F.B., Paulo L.G., Miranda A.L.P., Rocha S.O., Freitas A.C.C., Barreiro E.J. New pyrazolylhydrazone derivates as inhibitors of platelet aggregation. J. Pharm. Pharmacol. 45:1993;646-649.
4. Barreiro E.J., Fraga C.A.M., Miranda A.L.P., Rodrigues C.R. Química Medicinal de N-acilidrazonas: protótipos de fármacos analgésicos, anti-inflamatórios e anti-trombóticos. Quim. Nova. 25:2002;129-148.
5. Figueiredo J.M., Câmara C.A., Amarante E.G., Miranda A.L.P.M., Santos F.M., Rodrigues C.R., Fraga C.A.M., Barreiro E.J. Design and synthesis of novel potent antinociceptive agents: methyl-imidazolyl-N-acylhydrazone derivates. Bioorg. Med. Chem. 8:2000;2243-2248.
6. Leite L.F.C.C., Ramos M.N., Silva J.B.P., Miranda A.L.P., Fraga C.A.M., Barreiro E.J. Synthesis and analgesic profile of novel N-containing heterocycle derivates: arylidene 3-phenyl-1,2,4-oxadiazole-5-carbohydrazide. Farmaco. 54:1999;747-757.
7. Lima P.C., Lima L.M., da Silva K.C.M., Léda P.H.O., de Miranda A.L.P., Fraga C.A.M., Barreiro E.J. Synthesis and analgesic activity of novel N-acylarylhydrazones and isosters, derived from natural safrole. Eur. J. Med. Chem. 35:2000;187-203.
8. Gürsoy A., Demirayak S., Çapan G., Erol K., Vural K. Synthesis and preliminary evaluation of new 5-pyrazolinone derivates as analgesic agents. Eur. J. Med. Chem. 35:2000;359-364.
9. Patani G.A., LaVoie E.J. Bioisosterism: a rational approach in drug design. Chem. Rev. 96:1996;3147-3176.
10. Majo V.J., Perumal P.T. Intermolecular cyclization of azides by iminium species. A novel method for the construction of nitrogen heterocycles under Vilsmeier conditions. J. Org. Chem. 63:1998;7136-7142.
11. Lai G., Anderson W.K. A simplified procedure for the efficient conversion of aromatic aldehydes into esters. Synth. Commun. 27:1997;1281-1283.
12. 13C NMR of bioactive isochromanylacetylaryhydrazone derivates. Magn. Reson. Chem. 36:1998;533-538.
13. Pereira A.S., Violante F.A., Neto F.R.A., Cardoso J.N., Fraga C.A.M., Barreiro E.J. Diastereomeric analysis of bioactive N-phenylpyrazole-4-acylhydrazone derivates by high resolution gas chromatography. Anal. Lett. 31:1998;719-732.
14. Whittle B.A. The use of changes in capillary permeability in mice to distinguish between narcotic and non narcotic analgesics. Br. J. Pharmacol. 22:1964;246-253.
15. Ferreira S.H. A new method for measuring variations of rat paw volume. J. Pharm. Pharmacol. 31:1979;648.