CF3-MQC

Last updated

CF3-MQC
CF3-MQC structure.png
Identifiers
  • 2-methyl-N-(2-methylphenyl)-5-oxo-4-[5-[2-(trifluoromethoxy)phenyl]furan-2-yl]-4,6,7,8-tetrahydro-1H-quinoline-3-carboxamide
PubChem CID
ChemSpider
Chemical and physical data
Formula C29H25F3N2O4
Molar mass 522.524 g·mol−1
3D model (JSmol)
  • CC1=CC=CC=C1NC(=O)C2=C(NC3=C(C2C4=CC=C(O4)C5=CC=CC=C5OC(F)(F)F)C(=O)CCC3)C
  • InChI=1S/C29H25F3N2O4/c1-16-8-3-5-10-19(16)34-28(36)25-17(2)33-20-11-7-12-21(35)26(20)27(25)24-15-14-22(37-24)18-9-4-6-13-23(18)38-29(30,31)32/h3-6,8-10,13-15,27,33H,7,11-12H2,1-2H3,(H,34,36)
  • Key:UZXHFTMRTRONRF-UHFFFAOYSA-N

CF3-MQC is an experimental drug developed by Arena Pharmaceuticals, which acts as a reasonably potent and highly selective antagonist for the free fatty acid receptor FFAR3 (GPR41), and is used for research into the function of this receptor. [1] [2] [3] It is unclear whether CF3-MQC is the same compound as AR399519, the only other synthetic FFAR3 antagonist currently available, as while they are both cited to the same 2006 patent which claims only six closely related example structures as FFAR3 antagonists, [4] the structure of AR399519 is not disclosed in the published sources. [5] [6]

References

  1. ↑ Ulven T (2012). "Short-chain free fatty acid receptors FFA2/GPR43 and FFA3/GPR41 as new potential therapeutic targets". Frontiers in Endocrinology. 3: 111. doi: 10.3389/fendo.2012.00111 . PMC   3462324 . PMID   23060857.
  2. ↑ Said H, Akiba Y, Narimatsu K, Maruta K, Kuri A, Iwamoto KI, et al. (August 2017). "FFA3 Activation Stimulates Duodenal Bicarbonate Secretion and Prevents NSAID-Induced Enteropathy via the GLP-2 Pathway in Rats". Digestive Diseases and Sciences. 62 (8): 1944–1952. doi:10.1007/s10620-017-4600-4. PMC   5511769 . PMID   28523577.
  3. ↑ Ulven ER, Quon T, Sergeev E, Barki N, Brvar M, Hudson BD, et al. (April 2020). "Structure-Activity Relationship Studies of Tetrahydroquinolone Free Fatty Acid Receptor 3 Modulators". Journal of Medicinal Chemistry. 63 (7): 3577–3595. doi:10.1021/acs.jmedchem.9b02036. PMC   7307922 . PMID   32141297.
  4. ↑ Leonard JN, et al. Gpr41 and modulators thereof for the treatment of insulin-related disorders. WO 2006/052566
  5. ↑ Engelstoft MS, Park WM, Sakata I, Kristensen LV, Husted AS, Osborne-Lawrence S, et al. (2013). "Seven transmembrane G protein-coupled receptor repertoire of gastric ghrelin cells". Molecular Metabolism. 2 (4): 376–392. doi:10.1016/j.molmet.2013.08.006. PMC   3854997 . PMID   24327954.
  6. ↑ Christiansen CB, Gabe MB, Svendsen B, Dragsted LO, Rosenkilde MM, Holst JJ (July 2018). "The impact of short-chain fatty acids on GLP-1 and PYY secretion from the isolated perfused rat colon". American Journal of Physiology. Gastrointestinal and Liver Physiology. 315 (1): G53 –G65. doi:10.1152/ajpgi.00346.2017. PMID   29494208.
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