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1218777-13-9 molecular structure
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(5E)-5-{[5-(4-fluorophenyl)furan-2-yl]methylidene}-1,3-thiazolidine-2,4-dione

ChemBase ID: 73126
Molecular Formular: C14H8FNO3S
Molecular Mass: 289.2816232
Monoisotopic Mass: 289.02089234
SMILES and InChIs

SMILES:
c1(ccc(cc1)c1oc(cc1)/C=C/1\C(=O)NC(=O)S1)F
Canonical SMILES:
O=C1S/C(=C/c2ccc(o2)c2ccc(cc2)F)/C(=O)N1
InChI:
InChI=1S/C14H8FNO3S/c15-9-3-1-8(2-4-9)11-6-5-10(19-11)7-12-13(17)16-14(18)20-12/h1-7H,(H,16,17,18)/b12-7+
InChIKey:
UFBTYTGRUBUUIL-KPKJPENVSA-N

Cite this record

CBID:73126 http://www.chembase.cn/molecule-73126.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(5E)-5-{[5-(4-fluorophenyl)furan-2-yl]methylidene}-1,3-thiazolidine-2,4-dione
IUPAC Traditional name
(5E)-5-{[5-(4-fluorophenyl)furan-2-yl]methylidene}-1,3-thiazolidine-2,4-dione
Synonyms
CAY10505
CAS Number
1218777-13-9
PubChem SID
162038046
PubChem CID
1204893

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price
Selleck Chemicals
S2682 external link Add to cart Please log in.
Data Source Data ID
PubChem 1204893 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 7.8939095  H Acceptors
H Donor LogD (pH = 5.5) 2.6184042 
LogD (pH = 7.4) 2.5009174  Log P 2.620134 
Molar Refractivity 73.842 cm3 Polarizability 28.683813 Å3
Polar Surface Area 59.31 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Storage Condition
-20°C expand Show data source
Target
PI3K expand Show data source
Salt Data
Free Base expand Show data source

DETAILS

DETAILS

Selleck Chemicals Selleck Chemicals
Selleck Chemicals - S2682 external link
Biological Activity
Description CAY10505 is a PI3Kγ inhibitor with IC50 of 30 nM.
Targets PI3Kγ PI3Kα PI3Kβ PI3Kδ
IC50 30 nM 0.94 μM 20 μM 20 μM [1]
In Vitro CAY10505 selectively inhibits PI3Kγ isoform, with an IC50 of 30 nM better than the PI3Kα, β, and δ isoforms, with IC50 of 0.94, 20 and 20 μM, respectively. Tested against a panel of 80 other kinases including casein kinase 2, CAY10505 significantly inhibits only the unrelated casein kinase 2 (CK20) with an IC50 of 20 nM. CAY10505 also inhibits the phosphorylation of the PI3K substrate PKB/Akt in mouse macrophages with an IC50 of 228 nM. CAY10505 inhibits C5a-mediated?PKB/Akt phosphorylation?in Raw-264?macrophages, with an IC50 of 0.23?nM. In human monocytic cell line THP-1, MCP-1, binding to the GPCR chemokine receptor CCR2, strongly induces phosphorylation of PKB/Akt, which is effectively inhibited by 26 at IC50 values as low as 0.4 μM. CAY10505 inhibits MCP-1-mediated chemotaxis in wild-type primary monocytes in a concentration-dependent manner with an IC50 of 52 μM, as well as in the monocytic cell line THP-1 with an IC50 of 53 μM. [1]
In Vivo Oral administration of CAY10505 at 10 mg/kg results in moderate reduction of neutrophil recruitment by 35%, almost matching the result observed in PI3Kγ-deficient mice. [1] Five weeks of deoxycorticosterone acetate salt (DOCA) administration are followed by 7 days of daily administration of PI3Kγ inhibitor CAY10505 at a dose of 0.6 mg/kg (p.o.), which significantly improves acetylcholine-induced endothelium dependent relaxation, serum nitrate and (or) nitrite level, glutathione level, and the vascular endothelial lining in hypertensive rats. [2]
Clinical Trials
Features
Protocol
Kinase Assay [1]
PI3Kγ lipid kinase assay A PI3Kγ lipid kinase assay, based on the neomycin-coated scintillation proximity assay (SPA) bead technology, is performed in 384-well plates using ATP/[γ33P]ATP and PtdIns as substrates. Kinase assays for IC50 value determinations of CAY10505 with PI3Kα, PI3Kβ, and PI3Kδ are carried out.
Cell Assay [1]
Cell Lines Bone marrow cells
Concentrations ~10 mM
Incubation Time 3 hours
Methods Bone marrow cells are isolated, prepared, and stimulated. For in vitro chemotaxis, 107 5-day-derived BMDMs are suspended in 1 mL of medium containing 0.5% BSA and CAY10505 or DMSO and applied to the upper chamber of a transwell, 5 μm pore size, chemotaxis plate. An amount of 600 μL of medium containing MCP-1/CCL2 and inhibitors or DMSO is added to the lower chamber. After 3 hours of incubation at 37 °C and 5% CO2, the number of cells in the lower chamber is quantified with a Coulter.
Animal Study [2]
Animal Models Wistar albino rats
Formulation
Doses 0.6 mg/kg
Administration Administered via p.o.
References
[1] Pomel V, et al. J Med Chem, 2006, 49(13), 3857-3871.
[2] Tyagi S, et al. Can J Physiol Pharmacol, 2012, 90(7), 881-885.

REFERENCES

REFERENCES

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PATENTS

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