Fenchone Derivatives as a Novel Class of CB2 Selective Ligands: Design, Synthesis, X-ray Structure and Therapeutic Potential.
Camphanes
/ chemical synthesis
Cannabinoid Receptor Agonists
/ chemical synthesis
Chemistry Techniques, Synthetic
Dose-Response Relationship, Drug
Drug Design
Humans
Ligands
Models, Molecular
Molecular Structure
Norbornanes
/ chemical synthesis
Protein Binding
Receptor, Cannabinoid, CB2
/ agonists
Spectrum Analysis
Structure-Activity Relationship
cannabinoid agonists
fenchone
hCB2 receptor
inflammation
Journal
Molecules (Basel, Switzerland)
ISSN: 1420-3049
Titre abrégé: Molecules
Pays: Switzerland
ID NLM: 100964009
Informations de publication
Date de publication:
18 Feb 2022
18 Feb 2022
Historique:
received:
06
01
2022
revised:
09
02
2022
accepted:
14
02
2022
entrez:
25
2
2022
pubmed:
26
2
2022
medline:
3
3
2022
Statut:
epublish
Résumé
A series of novel cannabinoid-type derivatives were synthesized by the coupling of (1S,4R)-(+) and (1R,4S)-(-)-fenchones with various resorcinols/phenols. The fenchone-resorcinol derivatives were fluorinated using Selectfluor and demethylated using sodium ethanethiolate in dimethylformamide (DMF). The absolute configurations of four compounds were determined by X-ray single crystal diffraction. The fenchone-resorcinol analogs possessed high affinity and selectivity for the CB2 cannabinoid receptor. One of the analogues synthesized, 2-(2',6'-dimethoxy-4'-(2″-methyloctan-2″-yl)phenyl)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-ol (
Identifiants
pubmed: 35209170
pii: molecules27041382
doi: 10.3390/molecules27041382
pmc: PMC8878464
pii:
doi:
Substances chimiques
Camphanes
0
Cannabinoid Receptor Agonists
0
Ligands
0
Norbornanes
0
Receptor, Cannabinoid, CB2
0
fenchone
1195-79-5
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Références
Br J Pharmacol. 2012 Apr;165(8):2462-78
pubmed: 21449982
J Med Chem. 2013 Nov 14;56(21):8224-56
pubmed: 23865723
J Clin Invest. 2010 Aug;120(8):2953-66
pubmed: 20664173
Molecules. 2013 Jan 18;18(1):1227-54
pubmed: 23334570
J Pharmacol Exp Ther. 2002 May;301(2):679-89
pubmed: 11961073
Proc Natl Acad Sci U S A. 2015 Jul 14;112(28):8774-9
pubmed: 26124120
J Leukoc Biol. 2007 Dec;82(6):1382-9
pubmed: 17652447
Acta Crystallogr C Struct Chem. 2015 Jan;71(Pt 1):3-8
pubmed: 25567568
Life Sci. 2018 Jul 1;204:20-45
pubmed: 29729263
Angew Chem Int Ed Engl. 2004 Dec 27;44(2):192-212
pubmed: 15578736
Br J Pharmacol. 2014 Mar;171(6):1448-61
pubmed: 24308861
J Nat Prod. 2002 Feb;65(2):221-44
pubmed: 11858762
Front Pharmacol. 2021 Jul 30;12:702675
pubmed: 34393784
J Nat Prod. 1996 Jan;59(1):49-51
pubmed: 8984153
Trends Pharmacol Sci. 2020 Sep;41(9):665-677
pubmed: 32739033
J Med Chem. 2015 Nov 12;58(21):8315-59
pubmed: 26200936
Agents Actions. 1991 Jan;32(1-2):119-21
pubmed: 2058458
J Comput Chem. 2009 Dec;30(16):2785-91
pubmed: 19399780
Bioorg Med Chem. 1999 Dec;7(12):2905-14
pubmed: 10658595
Lipids Health Dis. 2013 Dec 28;12:189
pubmed: 24373672
Proc Natl Acad Sci U S A. 1999 Dec 7;96(25):14228-33
pubmed: 10588688
ChemMedChem. 2020 Aug 5;15(15):1374-1389
pubmed: 32578963
Acta Crystallogr A Found Adv. 2015 Jan;71(Pt 1):3-8
pubmed: 25537383