Novel Synthesis of C-Methylated Phytocannabinoids Bearing Anti-inflammatory Properties.
Journal
Journal of medicinal chemistry
ISSN: 1520-4804
Titre abrégé: J Med Chem
Pays: United States
ID NLM: 9716531
Informations de publication
Date de publication:
27 04 2023
27 04 2023
Historique:
medline:
3
5
2023
pubmed:
15
4
2023
entrez:
14
4
2023
Statut:
ppublish
Résumé
There is growing interest in non-psychoactive phytocannabinoids, namely cannabidiol (CBD), cannabigerol (CBG), and cannabichromene, as potential leads for novel therapeutic agents. In this study, we report on the development of new derivatives in which we methylated either position 4 of olivetol or the phenolic positions of olivetol, or both. We introduce a refinement on previously reported chemical procedures for phytocannabinoid derivatization as well as the biological evaluation of all derivatives in anti-inflammatory in vivo models. Compounds such as the CBD derivative,
Identifiants
pubmed: 37057997
doi: 10.1021/acs.jmedchem.2c01988
pmc: PMC10150364
doi:
Substances chimiques
olivetol
65OP0NEZ1P
Cannabidiol
19GBJ60SN5
Resorcinols
0
Anti-Inflammatory Agents
0
Cytokines
0
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
5536-5549Références
Tetrahedron Lett. 1969 Dec;(60):5349-52
pubmed: 5370765
Inorg Chem. 2020 Apr 6;59(7):5182-5193
pubmed: 32207294
Pharmacol Ther. 2016 Oct;166:128-35
pubmed: 27411675
Br J Pharmacol. 2012 Jun;166(4):1444-60
pubmed: 22300105
J Am Chem Soc. 1971 Jan 13;93(1):217-24
pubmed: 5538858
Antioxidants (Basel). 2020 Jan 13;9(1):
pubmed: 31941059
Br J Pharmacol. 2019 Dec;176(23):4537-4547
pubmed: 31368508
Int J Mol Sci. 2018 Jul 08;19(7):
pubmed: 29986533
Arzneimittelforschung. 1972 Nov;22(11):1995-2003
pubmed: 4633591
Sci Rep. 2016 Jul 19;6:29789
pubmed: 27430371
J Clin Pharmacol. 2002 Nov;42(S1):11S-19S
pubmed: 12412831
Front Pharmacol. 2019 Nov 20;10:1284
pubmed: 31824305
Tetrahedron Lett. 1967 Mar;12:1109-11
pubmed: 6039537
Pharmacol Res. 2020 Jul;157:104822
pubmed: 32335286
Medicina (Kaunas). 2019 Nov 18;55(11):
pubmed: 31752240
Life Sci. 2005 Dec 22;78(5):454-66
pubmed: 16242157
Perspect Medicin Chem. 2016 Jun 28;8:17-39
pubmed: 27398024
Biol Pharm Bull. 2011;34(5):774-8
pubmed: 21532172
Org Biomol Chem. 2005 Mar 21;3(6):1116-23
pubmed: 15750656
J Am Chem Soc. 1974 Sep 4;96(18):5860-5
pubmed: 4413630
Molecules. 2021 Mar 21;26(6):
pubmed: 33801057
Biochem Pharmacol. 2013 May 1;85(9):1306-16
pubmed: 23415610
Phytochem Anal. 2004 Nov-Dec;15(6):345-54
pubmed: 15595449
Eur J Pharmacol. 1998 Oct 16;359(1):1-18
pubmed: 9831287
J Med Chem. 2006 Feb 9;49(3):1113-7
pubmed: 16451075
Bioorg Med Chem Lett. 2016 Mar 1;26(5):1428-33
pubmed: 26832786
Science. 1970 Aug 7;169(3945):611-2
pubmed: 4987683
J Am Chem Soc. 1965 Jul 20;87:3273-5
pubmed: 14324315
Medchemcomm. 2013 Dec 1;4(12):
pubmed: 24363888
Life Sci. 1980 Jun 9;26(23):1991-5
pubmed: 7401911
Org Lett. 2000 Oct 19;2(21):3301-3
pubmed: 11029195
Molecules. 2019 Jul 25;24(15):
pubmed: 31349553
J Nat Prod. 2008 Aug;71(8):1427-30
pubmed: 18681481