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| Chemical and physical data | |
| Formula | C24H17Cl2F2NO4 |
| Molar mass | 492.30 g·mol−1 |
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TC-C 14G is a potent, high affinity inverse agonist of the CB1 receptor: (EC50 = 11 nM in cAMP assay; Ki = 4 nM). Demonstrates high efficacy in a hypothermia assay (ID50 = 5 mg/kg) in vivo.[1]
Similar to rimonabant (and related agents such as giminabant), TC-C 14G potentially might have use in the treatment of obesity.
Synthesis
editLiterature report:[2] Patent (Ex 108):[3] Prec:[4]
- 4-fluoroveratrole [398-62-9] (1)
- 4-bromo-5-fluoro-benzene-1,2-diol [656804-73-8] (2)
- 2,4-dichlorobenzotrifluoride [320-60-5] (3)
- Fluorobenzene [462-06-6] (4)
- 2,4-dichloro-4'-fluoro-diphenyldichloromethane [656803-77-9] (5)
- 5-bromo-2-(2,4-dichloro-phenyl)-6-fluoro-2-(4-fluoro-phenyl)-benzo[1,3]dioxole, PC22475200 (6)
- PC22475029 (7)
References
edit- ^ "tc-c-14g_4345". Trocris.
- ^ Alig L, Alsenz J, Andjelkovic M, Bendels S, Bénardeau A, Bleicher K, et al. (April 2008). "Benzodioxoles: novel cannabinoid-1 receptor inverse agonists for the treatment of obesity". Journal of Medicinal Chemistry. 51 (7): 2115–27. doi:10.1021/jm701487t. PMID 18335976.
- ^ WO 2004013120, Alanine A, Beleicher K, Guba W, Haap w, Kuber D, Luebbers T, Plancher JM, Rogers-Evans M, Schneider G, Zuegge J, Roche O, "Novel benzodioxoles", assigned to Hoffmann La Roche Inc.
- ^ Furlano DC, Kirk KL (October 1986). "An improved synthesis of 4-fluoroveratrole. Efficient route to 6-fluoroveratraldehyde and 6-fluoro-D, L-DOPA". The Journal of Organic Chemistry. 51 (21): 4073–4075. doi:10.1021/jo00371a032.