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1214265-57-2 molecular structure
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N-{3-[(5-chloro-2-{[4-(4-methylpiperazin-1-yl)phenyl]amino}pyrimidin-4-yl)sulfanyl]phenyl}prop-2-enamide

ChemBase ID: 72562
Molecular Formular: C24H25ClN6OS
Molecular Mass: 481.0129
Monoisotopic Mass: 480.14990813
SMILES and InChIs

SMILES:
c1(ccc(cc1)Nc1ncc(c(n1)Sc1cc(ccc1)NC(=O)C=C)Cl)N1CCN(CC1)C
Canonical SMILES:
C=CC(=O)Nc1cccc(c1)Sc1nc(ncc1Cl)Nc1ccc(cc1)N1CCN(CC1)C
InChI:
InChI=1S/C24H25ClN6OS/c1-3-22(32)27-18-5-4-6-20(15-18)33-23-21(25)16-26-24(29-23)28-17-7-9-19(10-8-17)31-13-11-30(2)12-14-31/h3-10,15-16H,1,11-14H2,2H3,(H,27,32)(H,26,28,29)
InChIKey:
KIISCIGBPUVZBF-UHFFFAOYSA-N

Cite this record

CBID:72562 http://www.chembase.cn/molecule-72562.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
N-{3-[(5-chloro-2-{[4-(4-methylpiperazin-1-yl)phenyl]amino}pyrimidin-4-yl)sulfanyl]phenyl}prop-2-enamide
IUPAC Traditional name
N-{3-[(5-chloro-2-{[4-(4-methylpiperazin-1-yl)phenyl]amino}pyrimidin-4-yl)sulfanyl]phenyl}prop-2-enamide
Synonyms
WZ8040
CAS Number
1214265-57-2
PubChem SID
162037487
PubChem CID
44607531

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price
Selleck Chemicals
S1179 external link Add to cart Please log in.
Data Source Data ID
PubChem 44607531 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 14.157683  H Acceptors
H Donor LogD (pH = 5.5) 3.0823963 
LogD (pH = 7.4) 4.8407826  Log P 5.5048656 
Molar Refractivity 138.9463 cm3 Polarizability 51.435608 Å3
Polar Surface Area 73.39 Å2 Rotatable Bonds
Lipinski's Rule of Five false 

PROPERTIES

PROPERTIES

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

DETAILS

DETAILS

Selleck Chemicals Selleck Chemicals
Selleck Chemicals - S1179 external link
Research Area
Description Cancer
Biological Activity
Description WZ8040 is a novel mutant-selective irreversible EGFRT790M inhibitor.
Targets EGFR T790M
IC50
In Vitro WZ8040 is 30- to 100-fold more potent against EGFR T790M, and up to 100-fold less potent against wild-type EGFR, than quinazoline-based EGFR inhibitors such as CL-387785 and HKI-272. WZ8040 treatment potently inhibits the growth of HCC827 (EGFR Del E746_A750), PC9 (EGFR Del E746_A750), H3255 (EGFR L858R), H1975 (EGFR L858R/T790M), and PC9 GR (EGFR Del E746_A750/T790M) with IC50 of 1 nM, 6 nM, 66 nM, 9 nM, and 8 nM, respectively. WZ8040 weakly inhibits the growth of HCC827 GR (EGFR E746_A750/MET amp), H1819 (ERBB2 amp), Calu-3 (ERBB2 amp), H1781 (ERBB2 Ins G776V, C), and HN11 (EGFR & ERBB2 WT) with IC50 of >3.3 μM, 738 nM, 915 nM, 744 nM, and 1.82 μM, respectively. WZ8040 is not toxic up to 10 μM against A549 (KRAS mutant) or H3122 (EML4-ALK) cells. [1]
In Vivo
Clinical Trials
Features Inhibits EGFRT790M mutation but not wild-type EGFR.
Protocol
Cell Assay [1]
Cell Lines HCC827, H3255, HCC827 GR, H1975, PC9, PC9 GR, Calu-3, H1819, and Ba/F3
Concentrations Dissolved in DMSO, final concentrations ~10 μM
Incubation Time 72 hours
Methods Cells are exposed to increasing concentrations of WZ8040 for 72 hours. Growth is assessed using the MTS survival assay.
References
[1] Zhou W, et al. Nature, 2009, 462(7276), 1070-1074.

REFERENCES

REFERENCES

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PATENTS

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