Draft:TC-C 14G

TC-C 14G
Identifiers
	IUPAC name [2-(2,4-dichlorophenyl)-6-fluoro-2-(4-fluorophenyl)-1,3-benzodioxol-5-yl]-morpholin-4-ylmethanone;
CAS Number	656804-72-7;
PubChem CID	22475020;
ChemSpider	11407430;
ChEMBL	ChEMBL259656;
Chemical and physical data
Formula	C24H17Cl2F2NO4
Molar mass	492.30 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C1COCCN1C(=O)C2=CC3=C(C=C2F)OC(O3)(C4=CC=C(C=C4)F)C5=C(C=C(C=C5)Cl)Cl;
	InChI InChI=InChI=1S/C24H17Cl2F2NO4/c25-15-3-6-18(19(26)11-15)24(14-1-4-16(27)5-2-14)32-21-12-17(20(28)13-22(21)33-24)23(30)29-7-9-31-10-8-29/h1-6,11-13H,7-10H2; Key:VUCKSZWMRCSPME-UHFFFAOYSA-N;

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Instructions · What links here · TC-C 14G (talk: + · bio) · (log) · Copyvios report · reFill · Citation Bot · (Search: Google, Wikipedia) · Submitted 3 hours ago by Mo18ekula (talk: D · +) · Last edited 7 seconds ago by DannyS712 bot

TC-C 14G is a potent, high affinity inverse agonist of the CB1 receptor: (EC₅₀ = 11 nM in cAMP assay; K_i = 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

Literature 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

^ "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.

[1] "tc-c-14g_4345". Trocris.

[pmid18335976-2] 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.

[3] 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.

[4] 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.

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