Discovery of benzhydrylpiperazine derivatives as CB1 receptor inverse agonists via privileged structure-based approach

European Journal of Medicinal Chemistry

Volumn 45, Issue 3, 2010, Pages 1133-1139

  Meng, Tao ^a   Wang, Jue ^b   Peng, Hongli ^a   Fang, Guanghua ^a   Li, Min ^a   Xiong, Bing ^a   Xie, Xin ^b   Zhang, Yongliang ^a   Wang, Xin ^a   Shen, Jingkang ^a  

^a SHANGHAI INSTITUTE OF MATERIA MEDICA   (China)

^b National Center for Drug Screening   (China)

Author keywords

Anti obesity; Benzhydrylpiperazine; Cannabinoid receptor 1(CB1); Privileged structure

Indexed keywords

1 (CYCLOHEXYLCARBONYL) 4 [(2,4 DICHLOROPHENYL)(PHENYL)METHYL]PIPERAZINE; 1 [(2,4 DICHLORO PHENYL)(PHENYL)METHYL]PIPERAZINE; 1 [(2,4 DICHLOROPHENYL)(4 TOLYL)METHYL]PIPERAZINE; 1 [(4 CHLOROPHENYL)(2,4 DICHLOROPHENYL)METHYL]PIPERAZINE; 2 CHLORO 4 FLUOROPHENYL; 2 FLUORO 4 BROMOPHENYL; 2 FLUORO 4 CHLOROPHENYL; 2,4 DICHLOROPHENYL; 2,5 DICHLOROPHENYL; 2,6 DICHLOROPHENYL; 4 (1,1 DIMETHYLHEPTYL) 1',2',3',4',5',6' HEXAHYDRO 2,3' DIHYDROXY 6' (3 HYDROXYPROPYL)BIPHENYL; 4 [(2,4 DICHLOROPHENYL)(P TOLYL)METHYL]N PIPERIDIN 1 YLPIPERAZINE 1 CARBOXAMIDE; 4 [(2,4 DICHLOROPHENYL)(PHENYL)METHYL]N PIPERIDIN 1 YLPIPERAZINE 1 CARBOXAMIDE; 4 [(4 CHLOROPHENYL)(2,4 DICHLOROPHENYL)METHYL]N CYCLOHEXYLPIPERAZINE 1 CARBOXAMIDE; ANTIOBESITY AGENT; CANNABINOID 1 RECEPTOR; CANNABINOID 1 RECEPTOR ANTAGONIST; MOLECULAR SCAFFOLD; N BUTYL 4 [(2,4 DICHLOROPHENYL)(PHENYL)METHYL]PIPERAZINE 1 CARBOXAMIDE; N CYCLOHEXYL 4 [(2,4 DICHLOROPHENYL)(4 TOLYL)METHYL]PIPERAZINE 1 CARBOXAMIDE; N CYCLOHEXYL 4 [(2,4 DICHLOROPHENYL)(PHENYL)METHYL]PIPERAZINE 1 CARBOTHIOAMIDE; N CYCLOHEXYL 4 [(2,4 DICHLOROPHENYL)(PHENYL)METHYL]PIPERAZINE 1 CARBOXAMIDE; PIPERAZINE DERIVATIVE; RIMONABANT; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; CONTROLLED STUDY; DRUG ACTIVITY; DRUG BLOOD LEVEL; DRUG BRAIN LEVEL; DRUG DESIGN; DRUG HALF LIFE; DRUG IDENTIFICATION; DRUG POTENCY; IN VITRO STUDY; IN VIVO STUDY; MALE; NONHUMAN; OBESITY; RAT; STRUCTURE ACTIVITY RELATION; WEIGHT REDUCTION;

ADMINISTRATION, ORAL; ANIMALS; BENZHYDRYL COMPOUNDS; CELLS, CULTURED; CHO CELLS; CRICETINAE; CRICETULUS; INHIBITORY CONCENTRATION 50; MALE; MOLECULAR STRUCTURE; PIPERAZINES; RATS; RATS, SPRAGUE-DAWLEY; RECEPTOR, CANNABINOID, CB1; RECOMBINANT PROTEINS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 75849150801     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2009.12.018     Document Type: Article

References (20)

1. Li C., Ford E.S., Mokdad A.H., and Cook S. Pediatrics 118 (2006) 1390-1398
2. Mokdad A.H., Ford E.S., Bowman B.A., Dietz W.H., Vinicor F., Bales V.S., and Marks J.S. J. Am. Med. Assoc. 289 (2003) 76-79
3. Woods S.C. Am. J. Med. 120 (2007) 19-25
4. Colombo G., Orru A., Lai P., Cabras C., Maccioni P., Rubio M., Gessa G.L., and Carai M.A. Mol. Neurobiol. 36 (2007) 102-112
5. Lange J.H., and Kruse C.G. Chem. Rec. 8 (2008) 156-168
6. Svizenska I., Dubovy P., and Sulcova A. Pharmacol. Biochem. Behav. 90 (2008) 501-511
7. Xie S., Furjanic M.A., Ferrara J.J., McAndrew N.R., Ardino E.L., Ngondara A., Bernstein Y., Thomas K.J., Kim E., Walker J.M., Nagar S., Ward S.J., and Raffa R.B. J. Clin. Pharm. Ther. 32 (2007) 209-231
8. Christensen R., Kristensen P.K., Bartels E.M., Bliddal H., and Astrup A. Lancet 370 (2007) 1706-1713
9. Janero D.R., and Makriyannis A. Expert. Opin. Emerg. Drugs 14 (2009) 43-65
10. Jones D. Nat. Rev. Drug. Discov. 7 (2008) 961-962
11. Muccioli G.G., and Lambert D.M. Curr. Med. Chem. 12 (2005) 1361-1394
12. Lange J.H., and Kruse C.G. Drug. Discov. Today 10 (2005) 693-702
13. Adam J., Cowley P.M., Kiyoi T., Morrison A.J., and Mort C.J. Prog. Med. Chem. 44 (2006) 207-329
14. Evans B.E., Rittle K.E., Bock M.G., DiPardo R.M., Freidinger R.M., Whitter W.L., Lundell G.F., Veber D.F., Anderson P.S., Chang R.S., et al. J. Med. Chem. 31 (1988) 2235-2246
15. Patchett A.A., and Nargund R.P. Annu. Rep. Med. Chem. 35 (2000) 289-298
16. Muller G. Drug. Discov. Today 8 (2003) 681-691
17. Horton D.A., Bourne G.T., and Smythe M.L. Chem. Rev. 103 (2003) 893-930
18. King C.T., Weaver S.A., and Derr J.E. Am. J. Obstet. Gynecol. 93 (1965) 563-565
19. Neal R.A., and Halpert J. Annu. Rev. Pharmacol. Toxicol. 22 (1982) 321-339
20. Song K.S., Lee S.H., Chun H.J., Kim J.Y., Jung M.E., Ahn K., Kim S.U., Kim J., and Lee J. Bioorg. Med. Chem. 16 (2008) 4035-4051