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173529-46-9 molecular structure
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N-(4-methoxybenzenesulfonyl)-N-{2-[(E)-2-(1-oxo-1$l^{5}-pyridin-4-yl)ethenyl]phenyl}acetamide

ChemBase ID: 72707
Molecular Formular: C22H20N2O5S
Molecular Mass: 424.4696
Monoisotopic Mass: 424.10929275
SMILES and InChIs

SMILES:
c1cccc(c1N(S(=O)(=O)c1ccc(cc1)OC)C(=O)C)/C=C/c1cc[n+](cc1)[O-]
Canonical SMILES:
COc1ccc(cc1)S(=O)(=O)N(c1ccccc1/C=C/c1cc[n+](cc1)[O-])C(=O)C
InChI:
InChI=1S/C22H20N2O5S/c1-17(25)24(30(27,28)21-11-9-20(29-2)10-12-21)22-6-4-3-5-19(22)8-7-18-13-15-23(26)16-14-18/h3-16H,1-2H3/b8-7+
InChIKey:
OCKHRKSTDPOHEN-BQYQJAHWSA-N

Cite this record

CBID:72707 http://www.chembase.cn/molecule-72707.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
N-(4-methoxybenzenesulfonyl)-N-{2-[(E)-2-(1-oxo-1$l^{5}-pyridin-4-yl)ethenyl]phenyl}acetamide
IUPAC Traditional name
N-(4-methoxybenzenesulfonyl)-N-{2-[(E)-2-(1-oxo-1$l^{5}-pyridin-4-yl)ethenyl]phenyl}acetamide
Synonyms
IVX-214
HMN-214
CAS Number
173529-46-9
PubChem SID
162037628
PubChem CID
9888590

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price
Selleck Chemicals
S1485 external link Add to cart Please log in.
Data Source Data ID
PubChem 9888590 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
H Acceptors H Donor
LogD (pH = 5.5) 2.153845  LogD (pH = 7.4) 2.1538596 
Log P 2.1538599  Molar Refractivity 115.9067 cm3
Polarizability 44.205864 Å3 Polar Surface Area 89.14 Å2
Rotatable Bonds Lipinski's Rule of Five true 

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
PLK expand Show data source
Salt Data
Free Base expand Show data source

DETAILS

DETAILS

Selleck Chemicals Selleck Chemicals
Selleck Chemicals - S1485 external link
Research Area
Description Cancer
Biological Activity
Description HMN-214 (IVX-214) is a potent inhibitor of Polo-like kinase (Plk)1 with IC50 of 118 nM.
Targets Polo-like kinase (Plk)1
IC50 118 nM [1]
In Vitro HMN-214 is an oral prodrug that is rapidly converted to HMN-176. The in vitro data of HMN-214 are scarce. However, HMN-176, active metabolite of HMN-214, shows potent and broad-spectrumanti-tumor activity against various cancer cells, including HeLa, PC-3, DU-145, MIAPaCa-2, U937, MCF-7, A549, and WiDr, with a mean IC50 value of 118 nM. HMN-176 is also cytotoxic to drug-resistant human and murine cell lines, including P388/CDDP, P388/VCR, K2/CDDP, and K2/VP-16, with IC50 values ranging from 143 nM–265 nM. In HeLa cells, HMN-176 (3 μM) blocks cell cycle at G2/M phase. [1]In Doxorubicin-resistant K2/ARS cells, HMN-176 inhibits cell growth with an IC50 value of 2 μM. HMN-176 (3 μM) down-regulates the expression of the multidrug resistance gene (MDR1), due to the disturbance of NF-Y transcription factor binding to the MDR1 promoter. [2]In human RPE1 and CFPAC-1 cells, HMN-176 (2.5 μM) delays satisfaction of the spindle assembly checkpoint. HMN-176 (250 nM–2.5 μM) inhibits meiotic spindle assembly and aster formationin Spisula oocytes. HMN-176 (2.5 μM) also inhibits aster microtubule formation from human centrosomes. These results indicate that the anti-tumor activity of HMN-176 is at least partially via disrupting centrosome-mediated MT assembly during mitosis. [3]
In Vivo HMN-214 is an oral pro-drug of HMN-176 with improved oral absorption. HMN-214 (30 mg/kg) triggers no obvious neurotoxicity in mice. In mouse xenograft model of PC-3, A549, and WiDr cells, HMN-214 (10 mg/kg–20 mg/kg) inhibits tumor growth. [1]In nude mice model bearing multidrug-resistant KB-A.1 cells, HMN-214 (10 mg/kg–20 mg/kg) significantly suppresses MDR1 mRNA expression. [2]
Clinical Trials
Features
Protocol
Cell Assay [1]
Cell Lines HeLa, PC-3, DU-145, MIAPaCa-2, U937, MCF-7, A549, and WiDr cells
Concentrations 0–10 μM, dissolved in DMSO
Incubation Time 72 hours
Methods Cells are seeded into a 96-well microplate at a density of 3 × 103–1 × 104 cells/well. Dilutions of HMN-214 or HMN-176 are added the next day and the plate is incubated for 72 hours. The inhibition of growth is measured by the MTT assay and IC50 values are then obtained.
Animal Study [1]
Animal Models Male BALB/c nude mice bearing xenografts of PC-3, A549, and WiDr cells
Formulation Dissolved in 0.5% methylcellulose
Doses 10 mg/kg–20 mg/kg
Administration Oral gavage on a QD × 28 schedule
References
[1] Takagi M, et al. Invest New Drugs, 2003, 21(4), 387-399.
[2] Tanaka H, et al. Cancer Res, 2003, 63(20), 6942-6947.
[3] DiMaio MA, et al. Mol Cancer Ther, 2009, 8(3), 592-601.

REFERENCES

REFERENCES

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PATENTS

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