structure of (E)-(4-(2-(1H-indazol-3-yl)vinyl)phenyl)(piperazin-1-yl)methanone

(E)-(4-(2-(1H-indazol-3-yl)vinyl)phenyl)(piperazin-1-yl)methanone

CAS No.: 1000669-72-6
M. Wt: 332.399
M. Fa: C20H20N4O
InChI Key: YYLKKYCXAOBSRM-JXMROGBWSA-N
Appearance: White to light Yellow Solid

Names and Identifiers of 1000669-72-6

CAS Number

1000669-72-6

MDL Number

MFCD18385006

IUPAC Name

[4-[(E)-2-(1H-indazol-3-yl)ethenyl]phenyl]-piperazin-1-ylmethanone

InChI

InChI=1S/C20H20N4O/c25-20(24-13-11-21-12-14-24)16-8-5-15(6-9-16)7-10-19-17-3-1-2-4-18(17)22-23-19/h1-10,21H,11-14H2,(H,22,23)/b10-7+

InChIKey

YYLKKYCXAOBSRM-JXMROGBWSA-N

Canonical SMILES

C1CN(CCN1)C(=O)C2=CC=C(C=C2)C=CC3=NNC4=CC=CC=C43

Isomeric SMILES

C1CN(CCN1)C(=O)C2=CC=C(C=C2)/C=C/C3=NNC4=CC=CC=C43

UNII

2D9N67F58G

UNSPSC Code

12352100

Physical and chemical properties of 1000669-72-6

Acidity coefficient

13.76±0.40(Predicted)

Boiling Point

604.1±55.0 °C at 760 mmHg

Density

1.3±0.1 g/cm3

Exact Mass

332.163696

Flash Point

319.1±31.5 °C

Index of Refraction

1.723

LogP

2.07

Molecular Formula

C20H20N4O

Molecular Weight

332.399

PSA

61.02000

Solubility

Soluble in DMSO (>25 mg/ml)

Stability

Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 1 month.

Storage condition

-20°C

Vapour Pressure

0.0±1.7 mmHg at 25°C

Safety Information of 1000669-72-6

Pictograms

Signal Word

 Warning

Safety Data Sheet
Supports customized editing of SDS information and downloading in PDF documents.

Applications of 1000669-72-6

KW-2449 is primarily investigated for its applications in oncology, particularly:

  • Cancer Treatment: Targeting acute myeloid leukemia and other malignancies with FLT3 mutations.
  • Clinical Trials: Currently under evaluation in clinical settings to assess its efficacy and safety profile in patients resistant to existing therapies.

Interaction Studies of 1000669-72-6

Interaction studies have highlighted KW-2449's ability to maintain its efficacy despite the presence of human plasma proteins such as alpha1-acid glycoprotein. This characteristic suggests that KW-2449 can effectively inhibit its targets without significant interference from plasma protein binding, which can often limit the activity of other drugs.

Biological Activity of 1000669-72-6

KW-2449 exhibits potent antileukemic properties, particularly against cells harboring FLT3 mutations. Key findings include:

  • Cytotoxicity: Demonstrated significant cytotoxic effects on Molm14 cells with FLT3 internal tandem duplication mutations, primarily at concentrations that inhibit FLT3 autophosphorylation to less than 20% of baseline levels.
  • Growth Inhibition: In preclinical models, oral administration resulted in dose-dependent tumor growth inhibition with minimal bone marrow suppression, a critical factor for patient safety.
  • Mechanisms of Action: Induces apoptosis through multiple pathways including G1 arrest in FLT3-mutated leukemia and G2/M arrest in FLT3 wild-type leukemia cells.

Physical sample testing spectrum (NMR) of 1000669-72-6

Physical sample testing spectrum (NMR) of 1000669-72-6