Synthesis of new 1-phenyl-3-{4-[(2E)-3-phenylprop-2-enoyl]phenyl}-thiourea and urea derivatives with anti-nociceptive activity

Bioorganic and Medicinal Chemistry

Volumn 16, Issue 18, 2008, Pages 8526-8534

  dos Santos, Lorena ^a   Lima, Luíse Azevedo ^b   Cechinel Filho, Valdir ^b   Corrêa, Rogério ^b   de Campos Buzzi, Fátima ^b   Nunes, Ricardo José ^a  

^a FEDERAL UNIVERSITY OF SANTA CATARINA   (Brazil)

^b UNIVERSIDADE DO VALE DO ITAJAÍ   (Brazil)

Author keywords

Anti nociception; Chalcones; Thioureas; Ureas

Indexed keywords

1 (4 CHLOROPHENYL) 3 [4 (3 PHENYLPROP 2 ENOYL)PHENYL]THIOUREA; 1 PHENYL 3 [4 (3 PHENYLPROP 2 ENOYL)PHENYL]THIOUREA DERIVATIVE; 1 PHENYL 3 [4 (3 PHENYLPROP 2 ENOYL)PHENYL]UREA DERIVATIVE; ACETIC ACID; ACETYLSALICYLIC ACID; ANALGESIC AGENT; CAPSAICIN; DIPYRONE; FORMALDEHYDE; GLUTAMIC ACID; PARACETAMOL; SODIUM CHLORIDE; UNCLASSIFIED DRUG;

ANALGESIA; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTINOCICEPTION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; DOSE RESPONSE; DRUG BIOAVAILABILITY; DRUG PENETRATION; DRUG SOLUBILITY; DRUG STRUCTURE; DRUG SYNTHESIS; HOT PLATE TEST; INFRARED SPECTROSCOPY; MOUSE; NONHUMAN; PAIN; PROTON NUCLEAR MAGNETIC RESONANCE; WRITHING TEST;

ANALGESICS; ANIMALS; ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; BIOLOGICAL ASSAY; MICE; PAIN MEASUREMENT; STRUCTURE-ACTIVITY RELATIONSHIP; THIOUREA; UREA;

MUS;

EID: 51449097508     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2008.08.019     Document Type: Article

References (58)

1. Cabrera M., Simoens M., Falchi G., Lavaggi M.L., Piro L.E., Castellano E.E., Vidal A., Azqueta A., Monge A., Ceráin A.L., Sagrera G., Seoane G., Cerecetto H., and González M. Bioorg. Med. Chem. 15 (2007) 3356-3367
2. Lee S.H., Seo G.S., Kim H.S., Woo S.W., Ko G., and Sohn D.H. Biochem. Pharm. 72 (2006) 1322-1333
3. Araico A., Terencio M.C., Alcaraz M.J., Dominguez J.N., León C., and Ferrándiz M.L. Life Sci. 80 (2007) 2108-2117
4. Ducki S., Forrest R., Hadfield J.A., Kendall A., Lawrence N.J., McGown A.T., and Rennison D. Bioorg. Med. Chem. Lett. 8 (1998) 1051-1056
5. Yadav P.P., Gupta P., Chaturvedi A.K., Shukla P.K., and Maurya R. Bioorg. Med. Chem. 13 (2005) 1497-1505
6. Boeck P., Falcão C.A.B., Leal P.C., Yunes R.A., Cechinel-Filho V., Torres-Santos E.C., and Rossi-Bergmann B. Bioorg. Med. Chem. 14 (2006) 1538-1545
7. Yunes R.A., Chiaradia L.D., Leal P.C., Cechinel-Filho V., Torres-Santos E.C., Falcão C.A.B., and Rossi-Bergmann B. Curr. Trends Med. Chem. 4 (2006) 47-56
8. Dominguéz J.N., León C., Rodrigues J., Gamboa de Dominguez N., Gut J., and Rosenthal P.J. Farmaco 60 (2005) 307-311
9. Dominguéz J.N., León C., Rodrigues J., Gamboa de Dominguez N., Gut J., and Rosenthal P.J. J. Med. Chem. 48 (2005) 3654-3658
10. Lin L.M., Zhou Y., Flavin M.T., Zhou L.M., Nie W., and Chen F.C. Bioorg. Med. Chem. 10 (2002) 2795-2798
11. Furman C., Lebeau J., Fruchart J.C., Bernier J.L., Duriez P., Cotelle N., and Teissier E. J. Biochem. Mol. Toxicol. 15 (2001) 270-278
12. Santos L., Pedrosa R.C., Corrêa R., Cechinel-Filho V., Nunes R.J., and Yunes R.A. Arch. Pharm. 339 (2006) 541-546
13. Satyanarayana M., Tiwari P., Tripathi B.K., Srivastava A.K., and Pratap R. Bioorg. Med. Chem. 12 (2004) 883-889
14. Campos-Buzzi F., Padaratz P., Meira A.V., Corrêa R., Nunes R.J., and Cechinel-Filho V. Molecules 12 (2007) 896-906
15. Cechinel-Filho V., Vaz Z.R., Zunino L., Calixto J.B., and Yunes R.A. Eur. J. Med. Chem. 31 (1996) 833-839
16. Corrêa R., Pereira M.A.S., Buffon D., Santos L., Cechinel-Filho V., Santos A.R.S., and Nunes R.J. Arch. Pharm. Med. Chem. 334 (2001) 332-334
17. Cechinel-Filho V., Campos-Buzzi F., Padaratz P., Meira A.V., Corrêa R., and Nunes R.J. Molecules 12 (2007) 896-906
18. Yonova P.A., and Stoilkova G.M. J. Plant Growth Regul. 23 (2004) 280-291
19. Kim Y.J., Ryu J.H., Cheon Y.J., Lim H.J., and Jeon R. Bioorg. Med. Chem. Lett. 17 (2007) 3317-3321
20. Adeoye O., Ayandele A.A., and Odunola O.A. J. Agric. Biol. Sci. 2 (2007) 4-5
21. Venkatachalam T.K., Mão C., and Uckun F.M. Bioorg. Med. Chem. 12 (2004) 4275-4284
22. Bloom J.D., Dushin R.G., Curran K.J., Donahue F., Norton E.B., Terefenko E., Jonas T.R., Ross A.A., Feld B., Lang S.A., and Di-Grandi M.J. Bioorg. Med. Chem. 14 (2004) 3401-3406
23. Rojas J., Paya M., Domínguez J.N., and Ferrandiz L. Bioorg. Med. Chem. Lett. 12 (2002) 1951-1954
24. Rojas J., Paya M., Devesa L., Domínguez J.N., and Ferrandiz L. Naunyn-Schmiedeberg's Arch. Pharmacol. 368 (2003) 225-233
25. Araico A., Terencio M.C., Alcaraz M.J., Dominguez J.N., León C., and Ferrándiz M.L. Life Sci. 78 (2006) 2911-2918
26. Topliss J.G. J. Med. Chem. 15 (1972) 1006-1011
27. Topliss J.G. J. Med. Chem. 20 (1977) 463-469
28. Silverstein R.M., Webster F.X., Kiemle D., and Kiemle D.J. Spectrometric Identification of Organic Compounds. 7th ed. Vol. 1 (2005), John Wiley & Sons Inc., Hoboken 502
29. Domiguéz J.N., Charris J.E., Lobo G., Gamboa-Domiguez N., Moreno M.M., Riggione F., Sánchez E., Olson J., and Rosenthal P.J. Eur. J. Med. Chem. 36 (2001) 555-560
30. Gasull E.I., Silber J.J., Blanco S.E., Tomas F., Ferretti F.H., Go M.L., and Liu M. J. Mol. Struct.: THEOCHEM 503 (2000) 131-144
31. Balls M. Lab. Animal 27 (1998) 44-47
32. Festing M.F.W., Baumans V., Combes R.D., Halder M., Hendriksen C.F.M., Howard B.R., Lovell D.P., Moore G.J., Overend P., and Wilson M.S. ATLA Altern. Lab. Anim. 26 (1998) 283-301
33. Lipinski C.A., Lombardo F., Dominy B.W., and Feeney P.J. Adv. Drug Deliv. Rev. 46 (2001) 3-26
34. Lipinski C.A. Drug Discov. Today: Technol. 1 (2004) 337-341
35. Veber D.F., Johnson S.R., Cheng H.Y., Smith B.R., Ward K.W., and Kopple K.D. J. Med. Chem. 45 (2002) 2615-2623
36. Micó J.A., Gilbert-Rahola J., Casas J., Rojas O., Serrano M.I., and Serrano J.S. Eur. Neuropsychopharmacol. 7 (1997) 139-145
37. Togashi Y., Umeuchi H., Okano K., Ando N., Yoshizawa Y., Honda T., Kawamura K., Endoh T., Utsumi J., Kamei J., Tanaka T., and Nagase H. Eur. J. Pharmacol. 435 (2002) 259-264
38. Yasuda T., Endo M., Kon-No T., Kato T., Mitsuzuka M., and Ohsawa K. Biol. Pharm. Bull. 28 (2005) 1224-1228
39. Bolasco A., Fioravanti R., and Carradori S. Expert Opin. Ther. Patents 15 (2005) 1763-1782
40. Rolland A., Fleurentin J., Lanhers M.C., Misslin R., and Mortier F. Phytother. Res. 15 (2001) 377-381
41. Le Bars D., Gozariu M., and Cadeen S.W. Pharmacol. Rev. 53 (2001) 597-652
42. Costa B.B.C., Corrêa R., De Souza M.M., Pretto J.B., Ardenghi J.V., Campos-Buzzi F., and Cechinel-Filho V. Z. Naturforsch. 62 (2007) 201-206
43. Chen Y.F., Tsai H.Y., and Wu T.S. Planta Med. 61 (1995) 2-8
44. Vongtau H.O., Abbah J., Ngazal I.E., Kunle O.F., Chindo B.A., Otsapa P.B., and Gamaniel K.S. J. Ethnopharmacol. 90 (2004) 115-121
45. Tjoelsen A., Berge O.G., Hunskaar S., Roland J.H., and Hole K. Pain 51 (1992) 5-17
46. Coderre T.J., and Melzack R. J. Neurosci. 12 (1992) 3665-3670
47. Campos F., Corrêa R., de Souza M.M., Nunes R., Yunes R.J., and Cechinel-Filho V. Arzneim.-Forsch./Drug Res. 52 (2002) 455-461
48. Navarro D.F., Souza M.M., Neto R.A., Golin V., Niero R., Yunes R.A., Delle Monache F., and Cechinel Filho V. Phytomedicine 9 (2002) 427-432
49. Sakurada T., Katsumata K., Tan-No K., Sakurada S., and Kisara K. Neuropharmacology 31 (1992) 1279-1285
50. Beirith A., Santos A.R., Rodrigues A.L., Creczynski-Pasa T.B., and Calixto J.B. Eur. J. Pharmacol. 345 (1998) 233-245
51. Lavich T.R., Cordeiro R.S.B., Silva P.M.R., and Martins M.A. Braz. J. Med. Res. 38 (2005) 445-451
52. Herencia F., Férrandiz M.L., Ubeda A., Dominguez J.N., Charris J.E., Lobo G., and Alcaraz M.J. Bioorg. Med. Chem. Lett. 8 (1998) 1169-1174
53. Zimmermann M. Pain 16 (1983) 109-110
54. Br. J. Pharm. Chemother. 32 (1968) 295-310
55. Souza M.M., De Jesus R.A.P., Cechinel Filho V., and Schlemper V. Phytomedicine 107 (1998) 5103
56. Hunskaar A.T., and Hole K. Pain 30 (1987) 103-104
57. Campos-Buzzi F., Corrêa R., De Souza M.M., Yunes R.A., Nunes J.R., and Cechinel-Filho V. Drug Res. 52 (2002) 455-461
58. Eddy N.B., and Leimback D. J. Pharmacol. Exp. Ther. 107 (1953) 385-393