LY294002

LY294002

Names
IUPAC name 2-Morpholin-4-yl-8-phenylchromen-4-one
Other names 2-(4-Morpholinyl)-8-phenyl-4H-1-benzopyran-4-one
Identifiers
CAS Registry Number	154447-36-6 Y
ChEMBL	ChEMBL98350 N
ChemSpider	3835 N
InChI InChI=1S/C19H17NO3/c21-17-13-18(20-9-11-22-12-10-20)23-19-15(7-4-8-16(17)19)14-5-2-1-3-6-14/h1-8,13H,9-12H2 N Key: CZQHHVNHHHRRDU-UHFFFAOYSA-N N InChI=1/C19H17NO3/c21-17-13-18(20-9-11-22-12-10-20)23-19-15(7-4-8-16(17)19)14-5-2-1-3-6-14/h1-8,13H,9-12H2 Key: CZQHHVNHHHRRDU-UHFFFAOYAM
Jmol-3D images	Image
PubChem	3973
SMILES C1COCCN1C2=CC(=O)C3=C(O2)C(=CC=C3)C4=CC=CC=C4
Properties
Molecular formula	C19H17NO3
Molar mass	307.34 g·mol−1
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
N verify (what is: Y/N?)
Infobox references

LY294002 is a morpholine-containing chemical compound that is a potent inhibitor of phosphoinositide 3-kinases (PI3Ks).^[1] Two of these are the proto-oncogene serine/threonine-protein kinase (PIM1) and the phosphatidylinositol-4,5-bisphosphate 3-kinase catalytic subunit gamma isoform.^[2] With an IC₅₀ of 1.4 µM it is somewhat less potent than wortmannin, another well-known PI3 kinase inhibitor. However, LY294002 is a reversible inhibitor of PI3K whereas wortmannin acts irreversibly.^[3] Application of LY294002 causes a substantial acceleration of MEPP frequency (150 μM) at the frog neuromuscular junction through a mechanism that is independent of intraterminal calcium. LY294002 causes the release of MEPPs through a perturbation of synaptotagmin function.^[4]

LY294002 is also a BET inhibitor.^[5]

Application

Research

It has been shown that LY294002 administration has an additive effect on quercetin antiviral activity against hepatitis C virus. ^[6]

References

1. ↑ Maira et al. (2009). "PI3K inhibitors for cancer treatment: where do we stand?" (PDF). doi:10.1042/BST0370265.  CS1 maint: Explicit use of et al. (link)
2. ↑ "Card for LY294002 in DrugBank". DrugBank. Retrieved 2009-09-25. 
3. ↑ Chris J. Vlahos et al. (1994). "A Specific Inhibitor of Phosphatidylinositol 3-Kinase, 2-(4-Morpholinyl)-8-phenyl-4H-l-benzopyran-4-one (LY294002)" (PDF). Journal of Biological Chemistry 269 (7): 5241–5248. PMID 8106507.  CS1 maint: Explicit use of et al. (link)
4. ↑ Searl TJ, Silinsky EM. (Dec 2005). "LY 294002 inhibits adenosine receptor activation by a mechanism independent of effects on PI-3 kinase or casein kinase II". Purinergic Signal. 1 (4): 389–94. doi:10.1007/s11302-005-0778-6. PMC 2096559. PMID 18404524. 
5. ↑ Dittmann, Antje; Werner, Thilo; Chung, Chun-Wa; Savitski, Mikhail M.; Fälth Savitski, Maria; Grandi, Paola; Hopf, Carsten; Lindon, Matthew; Neubauer, Gitte; Prinjha, Rabinder K.; Bantscheff, Marcus; Drewes, Gerard (2013). "The Commonly Used PI3-Kinase Probe LY294002 is an Inhibitor of BET Bromodomains". ACS Chemical Biology: 131210150813004. doi:10.1021/cb400789e. 
6. ↑ Pisonero-Vaquero S (Mar 2014). "Modulation of PI3K-LXRα-dependent lipogenesis mediated by oxidative/nitrosative stress contributes to inhibition of HCV replication by quercetin.". Lab Invest. 94 (3): 262–274. doi:10.1038/labinvest.2013.156. PMID 24492281.