Multiparameter exploration of piperazine derivatives as δ-opioid receptor agonists for CNS indications

Bioorganic and Medicinal Chemistry Letters

Volumn 22, Issue 2, 2012, Pages 1169-1173

  McCauley Jr , John P ^a   Dantzman, Cathy L ^a   King, Megan M ^a   Ernst, Glen E ^a   Wang, Xia ^a   Brush, Kelly ^a   Palmer, William E ^a   Frietze, William ^a   Andisik, Donald W ^a   Hoesch, Valerie ^a   Doring, Kenneth ^a   Hulsizer, James ^a   Bui, Khanh H ^a   Liu, Jay ^a   Hudzik, Thomas J ^a   Wesolowski, Steven S ^a  

^a ASTRAZENECA   (United Kingdom)

Author keywords

ADME predictive models; Delta opioid agonist; hERG; Microsomal clearance; Permeability

Indexed keywords

CENTRAL NERVOUS SYSTEM AGENTS; DELTA OPIATE RECEPTOR; DELTA OPIATE RECEPTOR AGONIST; PIPERAZINE DERIVATIVE; POTASSIUM CHANNEL HERG;

ANIMAL CELL; ARTICLE; BINDING AFFINITY; CELL MEMBRANE PERMEABILITY; DRUG ABSORPTION; DRUG CLEARANCE; DRUG DISTRIBUTION; DRUG EXCRETION; DRUG INDICATION; DRUG METABOLISM; DRUG PENETRATION; DRUG POTENCY; DRUG RECEPTOR BINDING; DRUG SAFETY; DRUG SELECTIVITY; DRUG SYNTHESIS; LIVER MICROSOME METABOLISM; MOLECULAR MODEL; NONHUMAN; STEREOISOMERISM; STRUCTURE ACTIVITY RELATION;

ANIMALS; CENTRAL NERVOUS SYSTEM; COMPUTER SIMULATION; DOGS; DOSE-RESPONSE RELATIONSHIP, DRUG; ETHER-A-GO-GO POTASSIUM CHANNELS; HUMANS; MOLECULAR STRUCTURE; PIPERAZINES; RECEPTORS, OPIOID, DELTA; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84855716284     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2011.11.088     Document Type: Article

References (17)

1. M. Millan Pain 27 1986 303
2. M. Narita, N. Kuzumaki, M. Narita, C. Kaneko, N. Hareyama, M. Miyatake, K. Shindo, K. Miyoshi, M. Nakajima, Y. Nagumo, F. Sato, H. Wachi, Y. Seyama, and T. Suzuki J. Neurochem. 97 2006 1369
3. E. Berrocoso1, P. Sánchez-Blázquez, J. Garzón, and J.A. Mico1 Curr. Pharm. Design 15 2009 1612
4. A. Yekkirala, A. Kalyuzhny, and P. Portoghese ACS Chem. Neurosci. 1 2010 146
5. A. Pradhan, J. Becker, G. Scherrer, P. Tryoen-Toth, D. Filliol, A. Matifas, D. Massotte, C. Gavériaux-Ruff, and B. Kieffer PLoS ONE 4 2009 e5425
6. G. Dondio Il Farmaco 55 2000 178
7. D. Broom, E. Jutkiewicz, J. Folk, J. Traynor, K. Rice, and J. Woods Psychopharmacology 164 2002 42
8. S. Calderon, R. Rothman, F. Porreca, J. Flippen-Anderson, R. McNutt, H. Xu, L. Smith, E. Bilsky, P. Davis, and K. Rice J. Med. Chem. 37 1994 2125
9. H. Nagase, K. Kawai, J. Hayakawa, H. Wakita, A. Mizusuna, H. Matsuura, C. Tajima, Y. Takezawa, and T. Endoh Chem. Pharm. Bull. 46 1998 1695
10. B. Le Bourdonnec, R. Windh, C. Ajello, L. Leister, M. Gu, G. Chu, P. Tuthill, W. Barker, M. Koblish, D. Wiant, T. Graczyk, S. Belanger, J. Cassel, M. Feschenko, B. Brogdon, S. Smith, D. Christ, M. Derelanko, S. Kutz, P. Little, R. DeHaven, D. DeHaven-Hudkins, and R. Dolle J. Med. Chem. 51 2008 5893
11. N. Plobeck, D. Delorme, Z.-Y. Wei, H. Yang, F. Zhou, P. Schwarz, L. Gawell, H. Gagnon, B. Pelcman, R. Schmidt, S.Y. Yue, C. Walpole, W. Brown, E. Zhou, M. Labarre, K. Payza, S. St-Onge, A. Kamassah, P.-E. Morin, D. Projean, J. Ducharme, and E. Roberts J. Med. Chem. 43 2000 3878
12. P. Jones, A.M. Griffin, L. Gawell, R. Lavoie, D. Delorme, E. Roberts, W. Brown, C. Walpole, W. Xiao, J. Boulet, M. Labarre, M. Coupal, J. Butterworth, S. St-Onge, L. Hodzic, and D. Salois Bioorg. Med. Chem. Lett. 19 2009 5994
13. Based on model described in A. Cavalli, E. Poluzzi, F. De Ponti, and M. Recanatini J. Med. Chem. 45 2002 3844
14. MOE (Molecular Operating Environment) by CCG (Chemical Computing Group), Montreal, Canada.
15. P. Labute Pac. Symp. Biocomput. 4 1999 444
16. Polli, J. W.; Wring, S. A.; Humphreys, J. E.; Huang, L.; Morgan, J. B.; Webster, L. O.; Serabit-Singh, C. S. J. Pharmacol. Exp. Ther. 299, 620.
17. Dantzman, C. L.; King, M. M.; Ernst, G. E.; Wang, X.; McCauley Jr., J. P.; Andisik, D. W.; Brush, K.; Bui, K. H.; Frietze, W.; Hoesch, V.; Liu, J.; Palmer, W. E.; Spear, N.; Hudzik, T. J.; Wesolowski, S. S. Bioorg. Med. Chem. Lett., 2011 following paper.