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;

Submission declined on 5 December 2024 by Pygos (talk).

This submission does not appear to be written in the formal tone expected of an encyclopedia article. Entries should be written from a neutral point of view, and should refer to a range of independent, reliable, published sources. Please rewrite your submission in a more encyclopedic format. Please make sure to avoid peacock terms that promote the subject.

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Declined by Pygos 2 days ago. Last edited by Pygos 2 days ago. Reviewer: Inform author.

Resubmit

Please note that if the issues are not fixed, the draft will be declined again.

Comment: This article is very difficult to understand as it is written right now. Please fix its prose to make it more understandable to laypeople (or at least, those only with basic knowledge of biomolecules). Also, the majority of citations are devoted to the Synthesis section. More citations should be about its biological activity. Pygos (talk) 03:43, 5 December 2024 (UTC)

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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