Clobenpropit analogs as dual activity ligands for the histamine H3 and H4 receptors: Synthesis, pharmacological evaluation, and cross-target QSAR studies

Bioorganic and Medicinal Chemistry

Volumn 17, Issue 11, 2009, Pages 3987-3994

  Lim, Herman D ^a   Istyastono, Enade P ^a   van de Stolpe, Andrea ^a   Romeo, Giuseppe ^a   Gobbi, Silvia ^a   Schepers, Marjo ^a   Lahaye, Roger ^a   Menge, Wiro M B P ^a   Zuiderveld, Obbe P ^a   Jongejan, Aldo ^a   Smits, Rogier A ^a   Bakker, Remko A ^a   Haaksma, Eric E J ^a,b   Leurs, Rob ^a   de Esch, Iwan J P ^a  

^a LEIDEN UNIVERSITY   (Netherlands)

^b BOEHRINGER INGELHEIM RCV GMBH AND CO KG   (Austria)

Author keywords

Clobenpropit analogs; Cross target QSAR; GPCR; Histamine H3 receptor; Histamine H4 receptor; Selectivity

Indexed keywords

CLOBENPROPIT; CLOBENPROPIT DERIVATIVE; HISTAMINE H3 RECEPTOR; HISTAMINE H3 RECEPTOR AGONIST; HISTAMINE H3 RECEPTOR ANTAGONIST; HISTAMINE H4 RECEPTOR; HISTAMINE H4 RECEPTOR ANTAGONIST; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; DRUG RECEPTOR BINDING; DRUG SELECTIVITY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; NEUROBLASTOMA CELL; QUANTITATIVE STRUCTURE ACTIVITY RELATION; RECEPTOR AFFINITY;

HISTAMINE H3 ANTAGONISTS; HUMANS; IMIDAZOLES; LIGANDS; MALE; MOLECULAR STRUCTURE; PROTEIN BINDING; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; RECEPTORS, G-PROTEIN-COUPLED; RECEPTORS, HISTAMINE; RECEPTORS, HISTAMINE H3; THIOUREA;

EID: 65649084560     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2009.04.007     Document Type: Article

References (24)

1. Arrang J.M., Garbarg M., and Schwartz J.C. Nature 302 (1983) 832
2. Wijtmans M., Leurs R., and de Esch I. Expert Opin. Investig. Drugs 16 (2007) 967
3. Hough L.B. Mol. Pharmacol. 59 (2001) 415
4. de Esch I.J., Thurmond R.L., Jongejan A., and Leurs R. Trends Pharmacol. Sci. 26 (2005) 462
5. Thurmond R.L., Gelfand E.W., and Dunford P.J. Nat. Rev. Drug Disc. 7 (2008) 41
6. Sterk G.J., van der Goot H., and Timmerman H. Arch. Pharm. (Weinheim) 319 (1986) 624
7. Sterk G.J., Koper J., Van der Goot H., and Timmerman H. Eur. J. Med. Chem. Chim. Ther. 22 (1987) 491
8. De Esch I.J., Mills J.E., Perkins T.D., Romeo G., Hoffmann M., Wieland K., Leurs R., Menge W.M., Nederkoorn P.H., Dean P.M., and Timmerman H. J. Med. Chem. 44 (2001) 1666
9. de Esch I.J., Timmerman H., Menge W.M., and Nederkoorn P.H. Arch. Pharm. (Weinheim) 333 (2000) 254
10. Jongejan A., Lim H.D., Smits R.A., de Esch I.J., Haaksma E., and Leurs R. J. Chem. Inf. Model. 48 (2008) 1455
11. Eriksson L., Jaworska J., Worth A.P., Cronin M.T., McDowell R.M., and Gramatica P. Environ. Health Perspect. 111 (2003) 1361
12. Petitjean M. J. Chem. Inf. Comput. Sci. 32 (1992) 331
13. Lin, A. http://www.chemcomp.com/journal/descr.htm.
14. Wildman S.A., and Crippen G.M. J. Chem. Inf. Comput. Sci. 39 (1999) 868
15. Halgren T.A. J. Comput. Chem. 17 (1996) 490
16. Pearlman R.S., and Smith K.M. Perspect. Drug Disc. Des. 9/10/11 (1998) 339
17. Gasteiger J., and Marsili M. Tetrahedron 36 (1980) 3219
18. Lovenberg T.W., Roland B.L., Wilson S.J., Jiang X., Pyati J., Huvar A., Jackson M.R., and Erlander M.G. Mol. Pharmacol. 55 (1999) 1101
19. Liu C., Ma X., Jiang X., Wilson S.J., Hofstra C.L., Blevitt J., Pyati J., Li X., Chai W., Carruthers N., and Lovenberg T.W. Mol. Pharmacol. 59 (2001) 420
20. Lim H.D., van Rijn R.M., Ling P., Bakker R.A., Thurmond R.L., and Leurs R. J. Pharmacol. Exp. Ther. 314 (2005) 1310
21. Halgren T.A. J. Comput. Chem. 17 (1996) 553
22. Shahapurkar S., Pandya T., Kawathekar N., and Chaturvedi S.C. Eur. J. Med. Chem. 39 (2004) 899
23. Votano J.R., Parham M., Hall L.M., Hall L.H., Kier L.B., Oloff S., and Tropsha A. J. Med. Chem. 49 (2006) 7169
24. Rücker C., Rücker G., and Meringa M. J. Chem. Inf. Model. 47 (2007) 2345