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ChemicalBook--->CAS DataBase List--->505068-32-6

505068-32-6

505068-32-6 Structure

505068-32-6 Structure
IdentificationBack Directory
[Name]

Eggmanone
[CAS]

505068-32-6
[Synonyms]

Eggmanone
3-(2-methylprop-2-enyl)-2-(2-oxo-2-thiophen-2-ylethyl)sulfanyl-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidin-4-one
5,6,7,8-Tetrahydro-3-(2-methyl-2-propen-1-yl)-2-[[2-oxo-2-(2-thienyl)ethyl]thio]-[1]benzothieno[2,3-d]pyrimidin-4(3H)-one
[1]Benzothieno[2,3-d]pyrimidin-4(3H)-one, 5,6,7,8-tetrahydro-3-(2-methyl-2-propen-1-yl)-2-[[2-oxo-2-(2-thienyl)ethyl]thio]-
[Molecular Formula]

C20H20N2O2S3
[MOL File]

505068-32-6.mol
[Molecular Weight]

416.58
Chemical PropertiesBack Directory
[storage temp. ]

Store at -20°C
[solubility ]

≤0.5mg/ml in ethanol;10mg/ml in DMSO;5mg/ml in dimethyl formamide
[form ]

crystalline solid
[color ]

brown
Hazard InformationBack Directory
[Uses]

Eggmanone is used in the synthetic preparation of thieno/benzopyrimidinone inhibitors of Hedgehog signaling for potential cancer therapy. Phosphodiesterase (PDE) 4 inhibitor. Exhibits >40-fold selectivity over PDE3, PDE10, and PDE11
[Uses]

Type 4 cyclic nucleotide phosphodiesterase (PDE4) selectively inactivates the second messenger cAMP by hydrolyzing the phosphodiester bond, producing AMP. PDE4 has been reported to play a key regulatory role in Hedgehog signaling downstream of smoothened and, thus, represents a potential therapeutic target for Hedgehog-dependent cancers. Eggmanone is a selective inhibitor of PDE4 (IC50 = 72 nM) that antagonizes the Hedgehog signaling pathway. It demonstrates 40- to 50-fold lower potency at PDE3, PDE10, and PDE11 (IC50s = 3, 3.05, and 4.08 μM, respectively). Inhibition of PDE4 activity via eggmanone was shown to activate localized protein kinase A signaling, which, in turn, regulates Gli processing and translocation.[Cayman Chemical]
[Biological Activity]

eggmanone is a potent and selective pde4d3 inhibitor with ic50 value of 72 nm that antagonizes the hedgehog signaling pathway [1].hedgehog (hh) signaling plays an important role in vertebrate development, and its dysregulation is a driver of numerous malignancies. phosphodiesterase 4 (pde4) is a target for hh inhibition. eggmanone exerts its hh-inhibitory effects through selective antagonism of pde4, leading to protein kinase a activation and subsequent hh blockade [1].eggmanone is a potent and selective pde4 inhibitor that antagonizes the hedgehog signaling pathway. in sufu-/- mouse embryonic fibroblasts (mefs), eggmanone significantly reduced transcription levels of gli1 and ptc1. eggmanone functioned upstream of gli processing and nuclear translocation to exert its hh-inhibitory effects. eggmanone exhibited potent antagonism of pde4d3 with ic50 value of 0.072 μm, approximately 40- to 50-fold selective over pde3a, pde10a2, and pde11a4 (ic50s = 3, 3.05, and 4.08 μm, respectively). in shh-light2 cells transfected with pde4d3, eggmanone restored the increased hh signaling [1].
[storage]

Store at -20°C
[References]

[1]. williams ch, hempel je, hao j, et al. an in vivo chemical genetic screen identifies phosphodiesterase 4 as a pharmacological target for hedgehog signaling inhibition. cell rep. 2015 apr 7;11(1):43-50.
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