5-(4-Chlorophenyl)-5,6-dihydro-1,3-oxazepin-7(4H)-one derivatives as lipophilic cyclic analogues of baclofen: Design, synthesis, and neuropharmacological evaluation

Bioorganic and Medicinal Chemistry

Volumn 16, Issue 17, 2008, Pages 7983-7991

  Abdel Hafez, Atef A ^a   Abdel Wahab, Basel A ^b  

^a Assiut University   (Egypt)

^b Assiut University Faculty of Medicine   (Egypt)

Author keywords

1,3 Oxazepinone; Baclofen; GABA agonist; Lipophilicity; Neuropharmacological activity

Indexed keywords

2 BENZYL 5 (4 CHLOROPHENYL) 5,6 DIHYDRO 1,3 OXAZEPIN 7(4H) ONE DERIVATIVE; 4 AMINOBUTYRIC ACID RECEPTOR STIMULATING AGENT; 5 (4 CHLOROPHENYL) 2 (DEC 8 ENYL) 5,6 DIHYDRO 1,3 OXAZEPIN 7(4H) ONE DERIVATIVE; 5 (4 CHLOROPHENYL) 5,6 DIHYDRO 1,3 OXAZEPIN 7(4H) ONE DERIVATIVE; ACETIC ANHYDRIDE; BACLOFEN; UNCLASSIFIED DRUG;

ANALGESIA; ANIMAL EXPERIMENT; ARTICLE; BIOAVAILABILITY; COGNITIVE DEFECT; CONTROLLED STUDY; CYCLIZATION; DRUG DESIGN; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; INFRARED SPECTROSCOPY; LIPOPHILICITY; MALE; MASS SPECTROMETRY; MOUSE; MUSCLE RELAXATION; NEUROPHARMACOLOGY; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE;

ANIMALS; BACLOFEN; COGNITION DISORDERS; CYCLIZATION; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG DESIGN; DRUG EVALUATION, PRECLINICAL; GABA AGONISTS; HYDROPHOBICITY; INJECTIONS, INTRAPERITONEAL; MAGNETIC RESONANCE SPECTROSCOPY; MALE; MICE; MOLECULAR STRUCTURE; MOTOR ACTIVITY; MUSCLE RELAXATION; OXAZEPINES; PAIN; RECEPTORS, GABA-B; REFERENCE STANDARDS; STEREOISOMERISM;

EID: 50349083404     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2008.07.064     Document Type: Article

References (46)

1. Zhenliang C., Zhiyong C., Yaozhong J., and Werhao H. Tetrahedron 61 (2005) 1579
2. Barnard E.A., Skolnick P., Olsen R.W., Mohler H., Sieghart W., Biggio G., Braestrup C., Bateson A.N., and Langer S.Z. Pharmacol. Rev. 50 (1998) 291
3. Calver A.R., Davies C.H., and Pangalos M. Neurosignals 11 (2002) 299
4. Robbins M.J., Calver A.R., Fillipov A.K., Couve A., Moss S.J., and Pangalos M.N. J. Neurosci. 21 (2001) 8043
5. Pin J.P., Galvez T., Franek M., Bertrand H.O., Prezeau L., and Blahos J. Eur. J. Neurosci. 12 (2000) 67
6. Bowery N.G., Bettler B., Froestl W., Gallagher J.P., Marshall F., Raiteri M., Bonner T.I., and Enna S.J. Pharmacol. Rev. 54 (2002) 247
7. Buda-Levin A., Wojnicki F.H.E., and Corwin R.L. Physiol. Behav. 86 (2005) 176
8. Brogden R.N., Speight T.M., and Avery G.S. Drugs 8 (1974) 1
9. Bowery N.G. Curr. Opin. Pharmacol. 6 (2006) 37
10. Katz R.T., and Campagnolo D.I. Phys. Med. Rehabil.: State Art Rev. 8 (1994) 473
11. Young R.R., Emre M., and Nance P.W. Neurologist 3 (1997) 261
12. Dimitrijevic M.R. J. Neurol. Rehabil. 9 (1995) 97
13. Terrence C.F., Fromm G.H., and Roussan M.S. Arch. Neurol. 40 (1983) 28
14. Penn R.D., Savoy S.M., Corcos D., Latash M., Gottlieb G., and Kroin J. Engl. J. Med. 320 (1989) 1517
15. Francois B., Vacher P., Roustan J., Salle J.Y., Vidal J., Moreau J.J., and Vignon P. J. Trauma 50 (2001) 158
16. Erdine S., and Yucel A. Pain Rev. 2 (1995) 227
17. Velarde C., Zuniga R.E., and Abram S.E. Reg. Anesth. Pain Med. 25 (2000) 76
18. Leo A.J. Chem. Rev. 63 (1993) 1281
19. Boehm S., Peden L., Adron H.R., and Blednov A. J. Pharmacol. Exp. Ther. 309 (2004) 1154
20. Spooren W.P., Vassout A., Neijt H.C., Kuhn R., Gasparini F., Roux S., Porsolt R.D., and Gentsch C. J. Pharmacol. Exp. Ther. 295 (2000) 1267
21. Dunham N., and Miya T.S. J. Am. Pharm. Assoc. (Baltim.) 46 (1957) 208
22. Boissier J., and Simon P. The'rapie 15 (1960) 1170
23. Dambrova M., Zvejniece L., Liepinsh E., Cirule H., Zharkova O., Veinberg G., and Kalvinsh I. Eur. J. Pharamcol. 583 (2008) 128
24. Venable N., and Kelly P.H. Psychopharmacology (Berl.) 100 (1990) 215
25. Mombereau C., Kaupmann K., Froestl W., Sansig G., Van der Putten H., and Cryan J.F. Neuropsychopharmacology 29 (2004) 1050
26. Ketelaars C.E., Bollen E.L., Rigter H., and Bruinvels J. Life Sci. 42 (1988) 933
27. Shepherd J.K., Grewal S.S., Fletcher A., Bill D.J., and Dourish C.T. Psychopharmacology (Berl.) 116 (1994) 56
28. File S.E., Zharkovsky A., and Gulati K. Neuropharmacology 30 (1991) 183
29. File S.E., Zharkovsky A., and Hitchcott P.K. Prog. Neuropsychopharmacol. Biol. Psychiatry 16 (1992) 87
30. Addolorato G., Caputo F., Capristo E., Domenicali M., Bernardi M., Janiri L., Agabio R., Colombo G., Gessa G.L., and Gasbarrini G. Alcohol 37 (2002) 504
31. Drake R.G., Davis L.L., Cates M.E., Jewell M.E., Ambrose S.M., and Lowe J.S. Ann. Pharmacother. 37 (2003) 1177
32. Breslow M.F., Fankhauser M.P., Potter R.L., Meredith K.E., Misiaszek J., and Hope D.G. Am. J. Psychiatry 146 (1989) 353
33. Balerio G., and Rubio M. Pharmacol. Res. 46 (2002) 281
34. Cutting D.A., and Jordan C.C. Br. J. Pharmacol. 54 (1975) 171
35. Balerio G., and Rubio M. Pharmacol. Res. 46 (2002) 281
36. Swartzwelder H.S., Tilson H.A., McLamb R.L., and Wilson W.A. Psychopharmacology (Berl.) 92 (1987) 398
37. Castellano C., Brioni J.D., Nagahara A.H., and McGaugh J.L. Behav. Neural. Biol. 52 (1989) 170
38. Zarrindast M.R., Bakhsha A., Rostami P., and Shafaghi B. J. Psychopharmacol. 16 (2002) 313
39. Car H., Nadlewska A., and Wioeniewski K. Pol. J. Pharmacol. 52 (2000) 247
40. Car H., Oksztel R., Nadlewska A., and Wioeniewski K. Pharmacol. Res. 44 (2001) 329
41. Car H., and Wioeniewski K. Pol. J. Pharmacol. 51 (1999) 275
42. Car H., and Wioeniewski K. Pharmacol. Biochem. Behav. 59 (1998) 685
43. Zarrindast M.R., Lahiji P., Shafaghi B., and Sadegh M. Gen. Pharmacol. 31 (1998) 81
44. Berthelot P., Vaccher C., Flouquet N., Debaert M., Luyckx M., and Burnet C. J. Med. Chem. 34 (1991) 2557
45. Kerr D.I.B., and Ong J. Med. Res. Rev. 12 (1992) 593
46. Kerr D.I.B., Ong J., Doolette D.J., Abbenante J., and Prager R.H. Eur. J. Pharamcol. 96 (1993) 239