9-Aminomethyl-9,10-dihydroanthracene (AMDA) analogs as structural probes for steric tolerance in 5-HT2A and H1 receptor binding sites

Bioorganic and Medicinal Chemistry Letters

Volumn 20, Issue 3, 2010, Pages 935-938

  Shah, Jitesh R ^a   Mosier, Philip D ^a   Peddi, Srinivas ^a   Roth, Bryan L ^b   Westkaemper, Richard B ^a  

^a VIRGINIA COMMONWEALTH UNIVERSITY   (United States)

^b UNIVERSITY OF NORTH CAROLINA SCHOOL OF MEDICINE   (United States)

Author keywords

AMDA; G protein coupled receptor (GPCR); GPCR modeling; Phenylethylamines

Indexed keywords

(6,11 DIHYDROTETRACENE 11 YL)METHANAMINE; (7,12 DIHYDROTETRAPHENE 12 YL)METHANAMINE; (7,12-DIHYDROTETRAPHENE-3-METHOXY-12-YL)METHANAMINE; 9 AMINOMETHYL 9,10 DIHYDROANTHRACENE DERIVATIVE; AMINE; ANTHRACENE DERIVATIVE; BUTANOL; CARBENOID; HISTAMINE H1 RECEPTOR; METHYLAMINE; N PHENYLALKYL 9 AMINOMETHYL 9,10 DIHYDROANTHRACENE DERIVATIVE; RADIOLIGAND; SEROTONIN 2A RECEPTOR; UNCLASSIFIED DRUG; 9-(AMINOMETHYL)-9,10-DIHYDROANTHRACENE; SEROTONIN 1 RECEPTOR;

ARTICLE; BINDING AFFINITY; BINDING SITE; DRUG SELECTIVITY; LIGAND BINDING; MOLECULAR MODEL; STEREOCHEMISTRY; SUBSTITUTION REACTION; CHEMISTRY; COMPARATIVE STUDY; HUMAN; METABOLISM; PHYSIOLOGY; STEREOISOMERISM; STRUCTURE ACTIVITY RELATION;

ANTHRACENES; BINDING SITES; HUMANS; RECEPTOR, SEROTONIN, 5-HT2A; RECEPTORS, SEROTONIN, 5-HT1; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 74049127386     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2009.12.064     Document Type: Article

References (24)

1. Berger M., Gray J.A., and Roth B.L. Annu. Rev. Med. 60 (2009) 355
2. Nichols D.E., and Nichols C.D. Chem. Rev. 108 (2008) 1614
3. Rashid A., Manivet P., Nishio H., Pratuangdejkul J., Rajab M., Ishiguro M., Launay J.-M., and Nagatomo T. Life Sci. 73 (2003) 193
4. Shapiro D.A., Kristiansen K., Kroeze W.K., and Roth B.L. Mol. Pharmacol. 58 (2000) 877
5. Westkaemper R.B., and Glennon R.A. Curr. Top. Med. Chem. 2 (2002) 575
6. Dewkar G.K., Peddi S., Mosier P.D., Roth B.L., and Westkaemper R.B. Bioorg. Med. Chem. Lett. 18 (2008) 5268
7. Runyon S.P., Mosier P.D., Roth B.L., Glennon R.A., and Westkaemper R.B. J. Med. Chem. 51 (2008) 6808
8. Runyon S.P., Peddi S., Savage J.E., Roth B.L., Glennon R.A., and Westkaemper R.B. J. Med. Chem. 45 (2002) 1656
9. Runyon S.P., Savage J.E., Taroua M., Roth B.L., Glennon R.A., and Westkaemper R.B. Bioorg. Med. Chem. Lett. 11 (2001) 655
10. Shah J.R., Mosier P.D., Roth B.L., Kellogg G.E., and Westkaemper R.B. Bioorg. Med. Chem. 17 (2009) 6496
11. Individual amino acid residues of the receptor are identified by the traditional residue identifier indicating the residue's position in the primary amino acid sequence, followed by the general Ballesteros-Weinstein GPCR residue identifier as a superscript. See:. Ballesteros J.A., and Weinstein H. Methods Neurosci. 25 (1995) 366
12. Klabunde T., Giegerich C., and Evers A. J. Med. Chem. 52 (2009) 2923
13. Trivedi B.K., Bristol J.A., Bruns R.F., Haleen S.J., and Steffen R.P. J. Med. Chem. 31 (1988) 271
14. Scopes D.I., Barrio J.R., and Leonard N.J. Science 195 (1977) 296
15. Ludeman S.M., and Zon G. J. Med. Chem. 18 (1975) 1251
16. Chang-Fong J., Addo J., Dukat M., Smith C., Mitchell N.A., Herrick-Davis K., Teitler M., and Glennon R.A. Bioorg. Med. Chem. Lett. 12 (2002) 155
17. Büttner F., Bergemann S., Guénard D., Gust R., Seitz G., and Thoret S. Bioorg. Med. Chem. 13 (2005) 3497
18. Campiani G., Ramunno A., Fiorini I., Nacci V., Morelli E., Novellino E., Goegan M., Mennini T., Sulivan S., Zisterer D.M., and Williams C.D. J. Med. Chem. 45 (2002) 4276
19. Chirapu S.R., Pachaiyappan B., Nural H.F., Cheng X., Yuan H., Lankin D.C., Abdul-Hay S.O., Thatcher G.R.J., Shen Y., Kozikowski A.P., and Petukhov P.A. Bioorg. Med. Chem. Lett. 19 (2009) 264
20. Bissantz C., Bernard P., Hibert M., and Rognan D. Proteins 50 (2003) 5
21. Chenna R., Sugawara H., Koike T., Lopez R., Gibson T.J., Higgins D.G., and Thompson J.D. Nucleic Acids Res. 31 (2003) 3497
22. Fiser A., and Šali A. In: Part D., Carter C.W.J., and Sweet R.M. (Eds). Methods in Enzymology: Macromolecular Crystallography Vol. 374 (2003), Academic Press, San Diego 461-491
23. Jones G., Willett P., Glen R.C., Leach A.R., and Taylor R. J. Mol. Biol. 267 (1997) 727
24. Zhang X.-X., and Lippard S.J. J. Org. Chem. 65 (2000) 5298