11970
1,3-Diphenyl-2-propenone
≥98.0% (GC)
Synonym(s):
Benzalacetophenone, Chalcone
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About This Item
Linear Formula:
C6H5CH=CHCOC6H5
CAS Number:
Molecular Weight:
208.26
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
202-330-2
Beilstein/REAXYS Number:
1210466
MDL number:
Assay:
≥98.0% (GC)
InChI key
DQFBYFPFKXHELB-VAWYXSNFSA-N
InChI
1S/C15H12O/c16-15(14-9-5-2-6-10-14)12-11-13-7-3-1-4-8-13/h1-12H/b12-11+
SMILES string
O=C(\C=C\c1ccccc1)c2ccccc2
assay
≥98.0% (GC)
solubility
dioxane: soluble 1 g/10 mL, clear, colorless
functional group
ketone, phenyl
Gene Information
rat ... Ar(24208)
Application
1,3-Diphenyl-2-propenone was used in the preparation of pharmacologically-interesting heterocyclic systems like pyrazolines and pyrimidines.
Biochem/physiol Actions
1,3-Diphenyl-2-propenone (chalcone) inhibits the proliferation of human breast cancer cell lines, MCF-7 and MDA-MB-231 by inducing apoptosis and blocking cell cycle progression in the G2/M phase. It is an inhibitor of Plasmodium falciparum cyclin-dependent protein kinases.
Storage Class
11 - Combustible Solids
wgk
WGK 3
ppe
dust mask type N95 (US), Eyeshields, Gloves
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Selective inhibition of Pfmrk, a Plasmodium falciparum CDK, by antimalarial 1,3-diaryl-2-propenones.
Jeanne A Geyer et al.
Bioorganic & medicinal chemistry letters, 19(7), 1982-1985 (2009-03-03)
The cyclin dependent protein kinases, Pfmrk and PfPK5, most likely play an essential role in cell cycle control and differentiation in Plasmodium falciparum and are thus an attractive target for antimalarial drug development. Various 1,3-diaryl-2-propenones (chalcone derivatives) which selectivity inhibit
Zi-Ming Feng et al.
Journal of natural products, 76(2), 270-274 (2013-02-08)
Hydroxysafflor yellow A (HSYA), a representative component of Carthamus tinctorius, has attracted much attention because of its remarkable cardiovascular activities. Its structure was originally reported in 1993 and has been widely cited to date. In our experiments, its solution structure
Jie Li et al.
Neuroscience letters, 535, 51-56 (2013-01-22)
Inflammation is a pivotal pathological progress in the development of ischemic stroke. Modulating inflammatory cytokines released by microglia is thought to be a potential strategy for the treatment of ischemic stroke. Hydroxy-safflor yellow A (HSYA), a chemical component of the
André Sousa et al.
The journal of physical chemistry. B, 117(6), 1901-1910 (2013-01-17)
Two oaklins guaiacylcatechinpyrylium (GCP) and syringylcatechinpyrylium (SCP) and a model compound deoxypeonidin (DOP) were synthesized, and the rate and equilibrium constants of the respective pH dependent network of chemical reactions were calculated. In contrast to anthocyanins, the three compounds possess
Chaoyun Wang et al.
Toxicology and applied pharmacology, 273(1), 59-67 (2013-09-03)
Intracellular reactive oxygen species (ROS) are derived from nicotinamide adenine dinucleotide phosphate (NADPH) oxidase. Angiotensin II (Ang II) can cause endothelial dysfunction by promoting intracellular ROS generation. Safflor yellow B (SYB) effectively inhibits ROS generation by upregulating Bcl-2 expression. In
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