EF-24

EF-24
Identifiers
	IUPAC name (3E,5E)-3,5-bis[(2-fluorophenyl)methylidene]piperidin-4-one;
CAS Number	342808-40-6;
PubChem CID	9885748;
ChemSpider	8061422;
UNII	O5YT36MST0;
ChEMBL	ChEMBL379849;
Chemical and physical data
Formula	C19H15F2NO
Molar mass	311.332 g·mol−1
3D model (JSmol)	Interactive image;
	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 to improve upon these properties, and has been found to be around 10 times 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

^ 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.
^ Mosley CA, Liotta DC, Snyder JP (2007). "Highly Active Anticancer Curcumin Analogues". The Molecular Targets and Therapeutic Uses of Curcumin in Health and Disease. Advances in Experimental Medicine and Biology. Vol. 595. pp. 77–103. doi:10.1007/978-0-387-46401-5_2. ISBN 978-0-387-46400-8. PMID 17569206.
^ 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.
^ 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.
^ 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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[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". The Molecular Targets and Therapeutic Uses of Curcumin in Health and Disease. Advances in Experimental Medicine and Biology. Vol. 595. pp. 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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