EF-24

EF-24
Identifiers
IUPAC name
  • (3E,5E)-3,5-bis[(2-fluorophenyl)methylidene]piperidin-4-one
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
Chemical and physical data
FormulaC19H15F2NO
Molar mass311.332 g·mol−1
3D model (JSmol)
SMILES
  • C\1NC/C(=C\C2=CC=CC=C2F)/C(=O)/C1=C/C3=CC=CC=C3F
InChI
  • InChI=1S/C19H15F2NO/c20-17-7-3-1-5-13(17)9-15-11-22-12-16(19(15)23)10-14-6-2-4-8-18(14)21/h1-10,22H,11-12H2/b15-9+,16-10+
  • Key:NIVYQYSNRUIFIF-KAVGSWPWSA-N

EF-24 is a compound that is a synthetic analogue of curcumin, a bioactive phytochemical from turmeric. Curcumin has antioxidant, antibiotic, anti-inflammatory and anti-cancer properties in vitro but has low potency and very poor bioavailability when taken orally, resulting in limited efficacy. EF-24 was developed to try and improve upon these properties, and has been found to be around 10x more potent than curcumin and with much higher systemic bioavailability. It has never been developed for medical use, though research continues to investigate whether it may be useful as an adjuvant treatment for some cancers alongside conventional chemotherapy drugs.[1][2][3][4][5]

References

  1. ↑ Adams BK, Cai J, Armstrong J, Herold M, Lu YJ, Sun A, et al. (March 2005). "EF24, a novel synthetic curcumin analog, induces apoptosis in cancer cells via a redox-dependent mechanism". Anti-Cancer Drugs. 16 (3): 263–75. doi:10.1097/00001813-200503000-00005. PMID 15711178. S2CID 33132231.
  2. ↑ Mosley CA, Liotta DC, Snyder JP (2007). "Highly active anticancer curcumin analogues". Advances in Experimental Medicine and Biology. 595: 77–103. doi:10.1007/978-0-387-46401-5_2. ISBN 978-0-387-46400-8. PMID 17569206.
  3. ↑ He Y, Li W, Hu G, Sun H, Kong Q (2018). "Bioactivities of EF24, a Novel Curcumin Analog: A Review". Frontiers in Oncology. 8: 614. doi:10.3389/fonc.2018.00614. PMC 6297553. PMID 30619754.
  4. ↑ Li W, He Y, Zhang R, Zheng G, Zhou D (January 2019). "The curcumin analog EF24 is a novel senolytic agent". Aging. 11 (2): 771–782. doi:10.18632/aging.101787. PMC 6366974. PMID 30694217.
  5. ↑ Bazzaro M, Linder S (November 2020). "Dienone Compounds: Targets and Pharmacological Responses". Journal of Medicinal Chemistry. 63 (24): 15075–15093. doi:10.1021/acs.jmedchem.0c00812. PMC 7770821. PMID 33146523.
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