A new class of analgesic agents toward prostacyclin receptor inhibition: Synthesis, biological studies and QSAR analysis of 1-hydroxyl-2-substituted phenyl-4,4,5,5-tetramethylimidazolines

European Journal of Medicinal Chemistry

Volumn 43, Issue 5, 2008, Pages 1048-1058

  Zhao, Ming ^a   Li, Zheng ^b   Peng, Li ^a   Tang, Yu Rong ^c   Wang, Chao ^b   Zhang, Ziding ^c   Peng, Shiqi ^a  

^a CAPITAL MEDICAL UNIVERSITY   (China)

^b PEKING UNIVERSITY   (China)

^c CHINA AGRICULTURAL UNIVERSITY   (China)

Author keywords

Analgesic; QSAR; Tetramethylimidazoline; Vasorelaxation

Indexed keywords

1 HYDROXYL 2 (2' FLUOROPHEN 1' YL) 4,4,5,5 TETRAMETHYLIMIDAZOLINE; 1 HYDROXYL 2 (2' HYDROXYPHENYL) 4,4,5,5 TETRAMETHYLIMIDAZOLINE; 1 HYDROXYL 2 (2' NITROPHEN 1' YL) 4,4,5,5 TETRAMETHYLIMIDAZOLINE; 1 HYDROXYL 2 (2',4' DICHLOROPHEN 1' YL) 4,4,5,5 TETRAMETHYLIMIDAZOLINE; 1 HYDROXYL 2 (2',4' DIMETHOXYLPHEN 1' YL) 4,4,5,5 TETRAMETHYLIMIDAZOLINE; 1 HYDROXYL 2 (3' HYDROXYL 4' METHOXYLPHEN 1' YL) 4,4,5,5 TETRAMETHYLIMIDAZOLINE; 1 HYDROXYL 2 (3' HYDROXYPHEN 1' YL) 4,4,5,5 TETRAMETHYLIMIDAZOLINE; 1 HYDROXYL 2 (3' METHOXYL 4' HYDROXYPHEN 1' YL) 4,4,5,5 TETRAMETHYLIMIDAZOLINE; 1 HYDROXYL 2 (3' NITROPHEN 1' YL) 4,4,5,5 TETRAMETHYLIMIDAZOLINE; 1 HYDROXYL 2 (3',4' DICHLOROPHEN 1' YL) 4,4,5,5 TETRAMETHYLIMIDAZOLINE; 1 HYDROXYL 2 (3',4' DIMETHOXYLPHEN 1' YL) 4,4,5,5 TETRAMETHYLIMIDAZOLINE; 1 HYDROXYL 2 (3',4' METHYLENDIOXYPHEN 1' YL) 4,4,5,5 TETRAMETHYLIMIDAZOLINE; 1 HYDROXYL 2 (4' BROMOPHEN 1' YL) 4,4,5,5 TETRAMETHYLIMIDAZOLINE; 1 HYDROXYL 2 (4' CHLOROPHEN 1' YL) 4,4,5,5 TETRAMETHYLIMIDAZOLINE; 1 HYDROXYL 2 (4' HYDROXYPHEN 1' YL) 4,4,5,5 TETRAMETHYLIMIDAZOLINE; 1 HYDROXYL 2 (4' METHOXYLPHEN 1' YL) 4,4,5,5 TETRAMETHYLIMIDAZOLINE; 1 HYDROXYL 2 (4' METHYLPHEN 1' YL) 4,4,5,5 TETRAMETHYLIMIDAZOLINE; 1 HYDROXYL 2 (4' N,N DIMETHYLAMINOPHEN 1' YL) 4,4,5,5 TETRAMETHYLIMIDAZOLINE; 1 HYDROXYL 2 (4' NITROPHEN 1' YL) 4,4,5,5 TETRAMETHYLIMIDAZOLINE; 1 HYDROXYL 2 (PHEN 1' YL) 4,4,5,5 TETRAMETHYLIMIDAZOLINE; ANALGESIC AGENT; IMIDAZOLINE DERIVATIVE; NORADRENALIN; PHENYL 4,4,5,5 TETRAMETHYLIMIDAZOLINE DERIVATIVE; PROSTACYCLIN RECEPTOR; PROSTACYCLIN RECEPTOR INHIBITOR;

ANALGESIC ACTIVITY; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; AORTA; ARTICLE; BLEEDING; CONTROLLED STUDY; DISEASE MODEL; DRUG STRUCTURE; DRUG SYNTHESIS; INFRARED SPECTROSCOPY; INSTITUTE FOR CANCER RESEARCH MOUSE; MALE; MOUSE; MULTIPLE LINEAR REGRESSION ANALYSIS; NONHUMAN; PAIN; PAIN THRESHOLD; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTITATIVE STRUCTURE ACTIVITY RELATION; REACTION ANALYSIS; STRUCTURE ANALYSIS; TAIL FLICK TEST; THIN LAYER CHROMATOGRAPHY; VASODILATATION;

ANALGESICS; ANIMALS; AORTA; HEMORRHAGE; IMIDAZOLINES; LINEAR MODELS; MICE; MICE, INBRED ICR; PAIN MEASUREMENT; PAIN THRESHOLD; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; RECEPTORS, EPOPROSTENOL; TAIL; VASODILATION;

EID: 42949100886     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2007.07.007     Document Type: Article

References (36)

1. Vendemiale G., Grattagliano I., and Altomare E. Int. J. Clin. Lab. Res. 29 (1999) 49-55
2. Valko M., Rhodes C.J., Moncol J., Izakovic M., and Mazur M. Chem. Biol. Interact. 160 (2006) 1-40
3. Cooke M.S., Evans M.D., Dizdaroglu M., and Lunec J. FASEB J. 17 (2003) 1195-1214
4. Terranova R., Sorace R., Romeo A., Mauro C.D., Romeo R., and Luca S. Minerva Med. 92 (2001) 405-410
5. Olanow C.W. (Suppl.). Ann. Neurol. 32 (1992) S2-S9
6. Bankson D.D., Kestin M., and Rifai N. Clin. Lab. Med. 13 (1993) 463-480
7. Jaswal S., Mehta H.C., Sood A.K., and Kaur J. Clin. Chim. Acta 338 (2003) 123-129
8. Mak J.C., and Chan-Yeung M.M. Curr. Opin. Pulm. Med. 12 (2006) 7-11
9. Sheu S.S., Nauduri D., and Anders M.W. Biochim. Biophys. Acta 1762 (2006) 256-265
10. Clark R.D., Jahangir A., Severance D., Salazar R., Chang T., Chang D., Jett M.F., Smithc S., and Bley K. Bioorg. Med. Chem. Lett. 14 (2004) 1053-1056
11. Anderson R.E., Kretzer F.L., and Rapp L.M. Adv. Exp. Med. Biol. 366 (1994) 73-86
12. Marchetto R., Schreier S., and Nakaie C.R. J. Am. Chem. Soc. 115 (1993) 11042-11043
13. Liu J., Zhao M., Wang C., and Peng S. Bioorg. Med. Chem. Lett. 13 (2003) 4065-4069
14. Tsunoda R., Okumura K., Ishizaka H., Matsunaga T., Tabuchi T., Yasue H., Akaike T., Sato K., and Maeda H. Eur. J. Pharmacol. 262 (1994) 55-63
15. Akaike T., Yoshida M., Miyamoto Y., Sato K., Kohno M., Sasamoto K., Miyazaki K., Ueda S., and Maeda H. Biochemistry 32 (1993) 827-832
16. Ullman E.F., Osiecki J.H., Boocock D.G.B., and Darcy R. J. Am. Chem. Soc. 94 (1972) 7049-7059
17. Vocci F.J., Petty S.K., and Dewey W.L. J. Pharmacol. Exp. Ther. 207 (1978) 892-894
18. Medakovic M., and Banic B. J. Pharm. Pharmacol. 16 (1964) 198-204
19. Bley K.R., Hunter J.C., Eglen R.M., and Smith J.A. Trends Pharmacol. Sci. 19 (1998) 141-147
20. Tetko I.V., Gasteiger J., Todeschini R., Mauri A., Livingstone D., Ertl P., Palyulin V.A., Radchenko E.V., Zefirov N.S., Makarenko A.S., Tanchuk V.Y., and Prokopenko V.V. J. Comput. Aided Mol. Des. 19 (2005) 453-463
21. Bonchev D. Information Theoretic Indices for Characterization of Chemical Structures (1983), RSP-Wiley, Chichetser, UK
22. Schuur J., and Gasteriger J. Anal. Chem. 69 (1997) 2398-2405
23. Gupta R.A., Gupta A.K., Soni L.K., and Kaskhedika S.G. Eur. J. Med. Chem. (2007) 10.1016/j.ejmech.2007.01.018
24. Saiz-Urra L., Gonzalez M.P., and Teijeira M. Bioorg Med. Chem. 14 (2006) 7347-7358
25. Moran P.A.P. Biometrika 37 (1950) 17-23
26. Doytchinova I., and Natcheva R. Acta Pharm. 47 (1997) 189-195
27. Wang X.-H., Tang Y., Xie Q., and Qiu Z.-B. Eur. J. Med. Chem. 41 (2006) 226-232
28. Mathur K.C., Gupta S., and Khadikar P.V. Bioorg. Med. Chem. 11 (2003) 1915-1928
29. Zhao M., Li Z., Wu Y., Tang Y.-R., Wang C., Zhang Z., and Peng S. Bioorg. Med. Chem. 15 (2007) 2815-2826
30. Cramer III R.D., Patterson D.E., and Bunce J.D. Prog. Clin. Biol. Res. 291 (1989) 161-165
31. Holland J.H. Adaptation in Natural and Artificial Systems. second ed. (1992), MIT Press, Cambridge, USA
32. Michalewicz Z. Genetic Algorithms + Data Structures = Evolution Programs (1992), Springer, New York, USA
33. Kubinyi H. Quant. Struct.-Act. Relat. 13 (1994) 393-401
34. Akaike H. IEEE Trans. Autom. Control AC-19 (1974) 713-716
35. Saiz-Urra L., Gonzalez M.P., Fall Y., and Gomez G. Eur. J. Med. Chem. 42 (2007) 64-70
36. Saiz-Urra L., Gonzalez M.P., and Teijeira M. Bioorg. Med. Chem. 15 (2007) 3565-3571