CoMFA and CoMSIA analyses on 1,2,3,4-tetrahydropyrrolo[3,4-b]indole and benzimidazole derivatives as selective CB2 receptor agonists

Journal of Molecular Modeling

Volumn 16, Issue 9, 2010, Pages 1481-1498

  Cichero, Elena ^a   Cesarini, Sara ^a   Mosti, Luisa ^a   Fossa, Paola ^a  

^a UNIVERSITY OF GENOA   (Italy)

Author keywords

3D QSAR; Cannabinoid receptor; CB2 agonist; CoMFA; CoMSIA

Indexed keywords

1,2,3,4 TETRAHYDROPYRROLO[3,4 B]INDOLE DERIVATIVE; BENZIMIDAZOLE DERIVATIVE; CANNABINOID 1 RECEPTOR; CANNABINOID 2 RECEPTOR AGONIST; INDOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; CHEMICAL STRUCTURE; COMPARATIVE MOLECULAR FIELD ANALYSIS; COMPARATIVE MOLECULAR SIMILARITY INDICES ANALYSIS; MOLECULAR MODEL; PRIORITY JOURNAL;

BENZIMIDAZOLES; HUMANS; HYDROGEN BONDING; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; INDOLES; MODELS, MOLECULAR; PYRAZOLES; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; RECEPTOR, CANNABINOID, CB2; STATIC ELECTRICITY; THERMODYNAMICS;

EID: 77955328050     PISSN: 16102940     EISSN: 09485023     Source Type: Journal    
DOI: 10.1007/s00894-010-0664-1     Document Type: Article

References (27)

1. SL Palmer GA Thakur A Makriyannis 2002 Cannabinergic ligands Chem Phys Lipids 121 3 19 10.1016/S0009-3084(02)00143-3 1:CAS:528:DC%2BD38Xpslansro%3D (Pubitemid 36044538)
2. AC Howlett F Barth TI Bonner G Cabral P Casellas WA Devane CC Felder M Herkenham K Mackie BR Martin R Mechoulam RG Pertwee 2002 International Union of Pharmacology. XXVII. Classification of cannabinoid receptors Pharmacol Rev 54 161 202 10.1124/pr.54.2.161 1:CAS:528:DC%2BD38XltVOiuro%3D (Pubitemid 34575709)
3. RG Pertwee 2001 Cannabinoid receptors and pain Prog Neurobiol 63 569 611 10.1016/S0301-0082(00)00031-9 1:CAS:528:DC%2BD3MXntlOksA%3D%3D (Pubitemid 32115433)
4. P Goya N Jagerovic L Hernandez-Folgado MI Martin 2003 Cannabinoids and neuropathic pain Mini Rev Med Chem 3 765 772 10.2174/1389557033487818 1:CAS:528:DC%2BD3sXotlWjsbY%3D
5. A Calignano G La Rana D Piomelli 2001 Antinociceptive activity of the endogenous fatty acid amide, palmitylethanolamide Eur J Pharmacol 419 191 198 10.1016/S0014-2999(01)00988-8 1:CAS:528:DC%2BD3MXksFCkt78%3D (Pubitemid 32568218)
6. V Di Marzo CS Breivogel Q Tao DT Bridgen RK Razdan AM Zimmer A Zimmer BR Martin 2000 Levels, metabolism, and pharmacological activity of anandamide in CB(1) cannabinoid receptor knockout mice: evidence for non-CB(1), non-CB(2) receptor-mediated actions of anandamide in mouse brain J Neurochem 75 2434 2444 10.1046/j.1471-4159.2000.0752434.x
7. N Hájos C Ledent TF Freund 2001 Novel cannabinoid-sensitive receptor mediates inhibition of glutamatergic synaptic transmission in the hippocampus Neuroscience 106 1 4 10.1016/S0306-4522(01)00287-1 (Pubitemid 32831068)
8. GT Whiteside GP Lee KJ Valenzano 2007 The role of the cannabinoid CB2 receptor in pain transmission and therapeutic potential of small molecule CB2 receptor agonists Curr Med Chem 14 917 936 10.2174/092986707780363023 1:CAS:528:DC%2BD2sXjsF2qt7o%3D (Pubitemid 46863619)
9. JC Ashton 2007 Cannabinoids for the treatment of inflammation Curr Opin Investig Drugs 2007 8 373 384
10. GM Giblin CT O'Shaughnessy A Naylor WL Mitchell AJ Eatherton BP Slingsby DA Rawlings P Goldsmith AJ Brown CP Haslam NM Clayton AW Wilson IP Chessell AR Wittington R Green 2007 Discovery of 2-[(2, 4-dichlorophenyl)amino]-N- [(tetrahydro- 2H-pyran-4-yl)methyl]-4-(trifluoromethyl)- 5- pyrimidinecarboxamide, a selective CB2 receptor agonist for the treatment of inflammatory pain J Med Chem 50 2597 2600 10.1021/jm061195+ 1:CAS:528: DC%2BD2sXkvVClurY%3D (Pubitemid 46896065)
11. J Guindon AG Hohmann 2008 Cannabinoid CB2 receptors:a therapeutic target for the treatment of inflammatory and neuropathic pain Br J Pharmacol 153 319 334 10.1038/sj.bjp.0707531 1:CAS:528:DC%2BD1cXovFCluw%3D%3D
12. AD Khanolkar D Lu M Ibrahim RI Duclos GA Thakur TP Malan F Porreca V Veerappan X Tian C George DA Parrish DP Papahatjis A Makriyannis 2007 Cannabilactones:a novel class of CB2 selective agonists with peripheral analgesic activity J Med Chem 50 6493 6500 10.1021/jm070441u 1:CAS:528:DC%2BD2sXhtlOnur7J (Pubitemid 350309089)
13. J Fernandez-Ruiz J Romero G Velasco RM Tolon JA Ramos M Guzman 2007 Trends Pharmacol Sci 28 39 45 10.1016/j.tips.2006.11.001 1:CAS:528: DC%2BD2sXitlOmsw%3D%3D (Pubitemid 46038536)
14. M Maccarrone N Battista D Centonze 2007 The endocannabinoid pathway in Huntington's disease: a comparison with other neurodegenerative diseases Prog Neurobiol 81 349 379 10.1016/j.pneurobio.2006.11.006 1:CAS:528: DC%2BD2sXjvFGqtLs%3D (Pubitemid 46528640)
15. D Centonze A Finazzi-Agro G Bernardi M Maccarrone 2007 The endocannabinoid system in targeting inflammatory neurodegenerative diseases Trends Pharmacol Sci 28 180 187 10.1016/j.tips.2007.02.004 1:CAS:528: DC%2BD2sXjslShu7o%3D (Pubitemid 46483718)
16. RJ McKallip C Lombard M Fisher BR Martin S Ryu S Grant PS Nagarkatti M Nagarkatti 2002 Targeting CB2 cannabinoid receptors as a novel therapy to treat malignant lymphoblastic disease Blood 100 627 634 10.1182/blood-2002-01-0098 1:CAS:528:DC%2BD38XlsVWgtLc%3D (Pubitemid 34761128)
17. G Velasco I Galve-Roperh C Sánchez C Blázquez M Guzmán 2004 Hypothesis: cannabinoid therapy for the treatment of gliomas? Neuropharmacology 47 315 323 10.1016/j.neuropharm.2004.04.016 1:CAS:528:DC%2BD2cXmtVCjtLk%3D (Pubitemid 38953222)
18. RG Pertwee 2002 Cannabinoids and multiple sclerosis Pharmacol Ther 95 165 174 10.1016/S0163-7258(02)00255-3 1:CAS:528:DC%2BD38XmtlKjsr8%3D (Pubitemid 35232134)
19. O Ofek M Karsak N Leclerc M Fogel B Frenkel K Wright J Tam M Attar-Namdar V Kram E Shohami R Mechoulam A Zimmer 2006 Peripheral cannabinoid receptor, CB2, regulates bone mass Bab I Proc Natl Acad Sci USA 103 696 701 10.1073/pnas.0504187103 1:CAS:528:DC%2BD28XhtVOhsr4%3D (Pubitemid 43153088)
20. AI Idris RJ Van't Hof IR Greig SA Ridge D Baker RA Ross SH Ralston 2005 Regulation of bone mass, bone loss and osteoclast activity by cannabinoid receptors Nat Med 11 774 779 10.1038/nm1255 1:CAS:528:DC%2BD2MXmt1aju7g%3D (Pubitemid 41021210)
21. ZL Lu JW Saldanha EC Hulme 2002 Seven-transmembrane receptors: crystals clarify Trends Pharmacol 23 140 146 10.1016/S0165-6147(00)01973-8 1:CAS:528:DC%2BD38XhsFCmsLk%3D (Pubitemid 34185416)
22. D Pagé H Yang W Brown C Walpole M Fleurent M Fyfe F Gaudreault S St-Onge 2007 New 1, 2, 3, 4-tetrahydropyrrolo[3, 4-b]indole derivatives as selective CB2 receptor agonists Bioorg Med Chem Lett 22 6183 6187 10.1016/j.bmcl.2007.09.019 (Pubitemid 47554690)
23. D Pagé E Balaux L Boisvert Z Liu C Milburn M Tremblay Z Wei S Woo X Luo YX Cheng H Yang S Srivastava F Fhou W Brown M Tomaszewski C Walpole L Hodzic S St-Onge C Godbout D Salois K Payza 2008 Novel benzimidazole derivatives as selective CB2 agonists Bioorg Med Chem Lett 13 3695 3700 10.1016/j.bmcl.2008.05.073 (Pubitemid 351794522)
24. MOE: Chemical Computing Group Inc. Montreal. H3A 2R7 Canada. http://www.chemcomp.com
25. RD Cramer III DE Patterson JD Bunce 1989 Recent advances in comparative molecular field analysis (CoMFA) Prog Clin Biol Res 291 161 165 1:CAS:528:DyaL1MXhs1Ggt7Y%3D
26. G Klebe U Abraham T Mietzner 1994 Molecular similarity indices in a comparative analysis (CoMSIA) of drug molecules to correlate and predict their biological activity J Med Chem 37 4130 4146 10.1021/jm00050a010 1:CAS:528:DyaK2cXmslWhu7Y%3D (Pubitemid 24379702)
27. Sybyl 7 0. Tripos Inc 1699 South Hanley Road. St Louis, MO. 63144. USA