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ChemicalBook--->CAS DataBase List--->331771-20-1

331771-20-1

331771-20-1 Structure

331771-20-1 Structure
IdentificationBack Directory
[Name]

ZM 447439
[CAS]

331771-20-1
[Synonyms]

ZM 447439
ZM 447439, >=98%
N-(4-((6-Methoxy-7-(3-Morpholinopropoxy)quinazolin-4-yl)aMino)phenyl)benzaMide
N-[4-[[6-METHOXY-7-[3-(4-MORPHOLINYL)PROPOXY]-4-QUINAZOLINYL]AMINO]PHENYL]BENZAMIDE
BenzaMide, N-[4-[[6-Methoxy-7-[3-(4-Morpholinyl)propoxy]-4-quinazolinyl]aMino]phenyl]-
[Molecular Formula]

C29H31N5O4
[MDL Number]

MFCD08703125
[MOL File]

331771-20-1.mol
[Molecular Weight]

513.588
Chemical PropertiesBack Directory
[Melting point ]

117-120°C
[Boiling point ]

639.7±55.0 °C(Predicted)
[density ]

1.282±0.06 g/cm3(Predicted)
[storage temp. ]

Desiccate at RT
[solubility ]

Soluble in DMSO (up to 50 mg/ml) or in Ethanol (up to 25 mg/ml).
[form ]

White solid
[pka]

13.01±0.70(Predicted)
[color ]

White
[Stability:]

Stable for 1 year from date of purchase? as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 3 months.
Hazard InformationBack Directory
[Chemical Properties]

Pale Yellow Solid
[Uses]

It is a potent and selective inhibitor of Aurora B kinase. Cells treated with ZM-447439 progress through interphase, enter mitosis and assemble bipolar spindles but chromosome alignment, segregation a nd cytokinesis all fail. It induces apoptosos in Hep2 cancer cells and in acute myeloid leukemia cell lines but its propensity to induce polyploidy does not inevitably result in apoptosis.
[Definition]

ChEBI: ZM447439 is a member of the class of quinazolines that is quinazoline which is substituted at positions 4, 6 and 7 by a (4-benzamidophenyl)nitrilo group, methoxy group and a 3-(morpholin-4-yl)propoxy group, respectively. It is an ATP-competitive inhibitor of Aurora A and Aurora B kinases with IC50 of 110 nM and 130 nM, respectively. It has a role as an Aurora kinase inhibitor, an antineoplastic agent and an apoptosis inducer. It is a member of benzamides, a member of quinazolines, an aromatic ether, a member of morpholines, a polyether, a secondary amino compound and a tertiary amino compound.
[storage]

room temperature (desiccate)
[References]

1) Ditchfield et al (2003) Aurora B couples chromosome alignment with anaphase by targeting BubR1, Mad2, and Cenp-E to kinetochores; J.Cell Biol. 161 267 2) Girdler et al. (2006) Validating Aurora B as an anti-cancer drug target; J. Cell Sci. 119 3664
Questions And AnswerBack Directory
[Description]

ZM 447439 is a selective and ATP-competitive inhibitor for Aurora A and Aurora B with IC50 of 110 nM and 130 nM, respectively. It is more than 8-fold selective for Aurora A/B than MEK1, Src, Lck and has little effect against CDK1/2/4, Plk1, Chk1, etc.
[Features]

An Aurora selective ATP-competitive inhibitor.
[In vitro]

In vitro, ZM-447439 selectively inhibits recombinant human Aurora A and B with IC50 values of 110 and 130 nM, respectively, while other protein kinases of diverse structural types including the mitotic kinases CDK1 and PLK1 are inhibited with IC50 values >10 μM. Aurora kinase inhibitor, ZM-447439 time-and dose-dependently inhibits the growth of all three cell lines with IC50 values of 3 μM (BON), 0.9 μM (QGP-1) and 3 μM (MIP-101) after 72 hours of continuous exposure. In addition, ZM-447439 potently induces cell apoptosis by promoting DNA fragmentation and caspase 3 and 7 activation, and arrests GEP-NET cells in the G0 /G1and G2/M phase of the cell cycle. In mouse embryo, inhibition of Aurora kinase activity by ZM-447439 results in abnormalities during mitosis by regulating the phosphorylation of histone H3 serine 10 (H3S10Ph) from G2 to metaphase with different perturbations in each embryonic cycle. A recent study shows that ZM-447439 exhibits growth inhibitory and proapoptotic effect on cervical cancer SiHa cells, and enhances the chemosensitivity to cisplatin
Spectrum DetailBack Directory
[Spectrum Detail]

ZM 447439(331771-20-1)1HNMR
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