CAS 852808-04-9|4-(4-{[2-(4-chlorophenyl)phenyl]methyl}piperazin-1-yl)-N-(4-{[(2R)-4-(dimethylamino)-1-(phenylsulfanyl)butan-2-yl]amino}-3-nitrobenzenesulfonyl)benzamide|4-(4-{[2-(4-chlorophenyl)phe...

General Information

Structure

Molecular Formula

C₄₂H₄₅ClN₆O₅S₂

Molecular Mass

813.4269

Exact Mass

812.25813825

Charge

InChI

InChI=1S/C42H45ClN6O5S2/c1-46(2)23-22-35(30-55-37-9-4-3-5-10-37)44-40-21-20-38(28-41(40)49(51)52)56(53,54)45-42(50)32-14-18-36(19-15-32)48-26-24-47(25-27-48)29-33-8-6-7-11-39(33)31-12-16-34(43)17-13-31/h3-21,28,35,44H,22-27,29-30H2,1-2H3,(H,45,50)/t35-/m1/s1

InChIKey

HPLNQCPCUACXLM-PGUFJCEWSA-N

Canonic Smiles

CN(CC[C@@H](Nc1ccc(cc1[N+](=O)[O-])S(=O)(=O)NC(=O)c1ccc(cc1)N1CCN(CC1)Cc1ccccc1c1ccc(cc1)Cl)CSc1ccccc1)C

Isomeric Smiles

c1cc(ccc1C(=O)NS(=O)(=O)c1ccc(c(c1)[N+](=O)[O-])N[C@@H](CSc1ccccc1)CCN(C)C)N1CCN(CC1)Cc1c(cccc1)c1ccc(cc1)Cl

Calculated Properties

JChem

Acid pKa

4.2773795

H Acceptors

H Donor

LogD (pH = 5.5)

4.559849

LogD (pH = 7.4)

6.3591967

Log P

7.4634604

Molar Refractivity

230.6089

Polarizability

88.638306

Polar Surface Area

130.81

Rotatable Bonds

Lipinski's Rule of Five

false

Data Source

Commercial Catalog

Academic Data

Data Source

Names and Identifiers

IUPAC name

4-(4-{[2-(4-chlorophenyl)phenyl]methyl}piperazin-1-yl)-N-(4-{[(2R)-4-(dimethylamino)-1-(phenylsulfanyl)butan-2-yl]amino}-3-nitrobenzenesulfonyl)benzamide

IUPAC Traditional name

4-(4-{[2-(4-chlorophenyl)phenyl]methyl}piperazin-1-yl)-N-(4-{[(2R)-4-(dimethylamino)-1-(phenylsulfanyl)butan-2-yl]amino}-3-nitrobenzenesulfonyl)benzamide

Synonyms

ABT-737ABT 7374-[4-[(4’-Chloro[1,1’-biphenyl]-2-yl)methyl]-1-piperazinyl]-N-[[4-[[(1R)-3-(dimethylamino)-1-[(phenylthio)methyl]propyl]amino]-3-nitrophenyl]sulfonyl]benzamide

Names and Identifiers

Registration numbers

CAS Number

852808-04-9

PubChem CID

11228183

PubChem SID

162037377

Registration numbers

Properties

Product Information

Salt Data

Free Base

Certificate of Analysis

Download link

Physical Property

Solubility

DMSO

Methanol

Melting Point

152-154°C

Apperance

Yellow Solid

Pharmacology Properties

Target

Bcl-2

Safety Information

Storage Condition

-20°C

-20°C Freezer

MSDS Link

Download link

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

Selleck Chemicals

S1002

Research Area

Description

Cancer

Protocol

Kinase Assay ^[1]

Fluorescence polarization assays

Binding affinity of GST-Bcl-2 family proteins to the FITC-conjugated BH3 domain of Bim (FITC-Ahx-DMRPEIWIAQELRRIGDEFNAYYAR) is determined. Briefly, 100 nM of GST-Bcl-2 family fusion proteins are incubated with serial dilutions of ABT-737 in PBS for 2 min. Then, 20 nM of FITC-Bim BH3 peptide (FITC-Ahx-DMRPEIWIAQELRRIGDEFNAYYAR) is added. Fluorescence polarization is measured using an Analyst TM AD Assay Detection System after 10 min using the 96-well black plate. Then IC50 are determined.

Cell Assay ^[4]

Cell Lines

SCLC cell lines NCI-H889, NCI-H1963, NCI-H1417, NCI-H146, NCI-187, DMS79, NCI-1048, NCI-H82, NCI-H196, H69AR, and DMS114

Concentrations

0.001-10 μM

Incubation Time

48 hours

Methods

SCLC cells are treated for 48 hours in 96-well tissue culture plates in a total volume of 100 μL tissue culture medium supplemented with 10% human serum. Viable cells are determined using the MTS assay.

Animal Study ^[1]

Animal Models

Scid mice injected with Luc-expressing FD/ΔRaf-1:ER cells

Formulation

1 g/mL stock solution of ABT-737 in DMSO is added to a mixture of 30% propylene glycol, 5% Tween 80, 65% D5W (5% dextrose in water) (pH 4?5; final concentration of DMSO ≤ 1%)

Doses

20 and 30 mg/kg

Administration

For intraperitoneal (i.p.) every day

References

[1] Konopleva M, et al. Cancer Cell, 2006, 10(5), 375-388.

[2] van Delft MF,et al. Cancer Cell, 2006, 10(5), 389-399.

[3] Del Gaizo Moore V, et al. J Clin Invest, 2007, 117(1), 112-121.

[4] Tahir SK, et al. Cancer Res, 2007, 67(3), 1176-1183.

[5] Ishitsuka K, et al. Cancer Lett, 2012, 317(2), 218-225.

[6] Hikita H, et al. Hepatology. 2010, 52(4), 1310-21.

[7] Whitecross KF, et al, Blood, 2009, 113(9), 1982-1991.

TRC

A112550

A selective inhibitor of BCL-2, in small cell lung cancer. ABT-737 induced dramatic regressions in tumors derived from some SCLC cell lines.

Molecule Details

References

PubChem Literature

From Data Sources

• Whitecross KF, et al, Blood, 2009, 113(9), 1982-1991.

• Del Gaizo Moore V, et al. J Clin Invest, 2007, 117(1), 112-121.

• Tahir SK, et al. Cancer Res, 2007, 67(3), 1176-1183.

• Hikita H, et al. Hepatology. 2010, 52(4), 1310-21.

• Ishitsuka K, et al. Cancer Lett, 2012, 317(2), 218-225.

• van Delft MF,et al. Cancer Cell, 2006, 10(5), 389-399.

• Konopleva M, et al. Cancer Cell, 2006, 10(5), 375-388.

• Trudel, S., et al.: Clin. Cancer Res., 13, 621 (2007)

• Ikegaki, N., et al.: Cancer Res., 54, 6 (1994)

• Kaiser, U., et al.: Lung Cancer, 15, 31 (1994)

• Rudin, C., et al.: J. Clin. Oncol., 22, 1110 ( 2004), Konopleva, M., et al.: Cancer Cell, 10, 375 (1994)

References

Bioactivity

PubChem BioAssay

Bioactivity

Data Source

Commercial Catalog

Academic Data

Names and Identifiers

IUPAC name

4-(4-{[2-(4-chlorophenyl)phenyl]methyl}piperazin-1-yl)-N-(4-{[(2R)-4-(dimethylamino)-1-(phenylsulfanyl)butan-2-yl]amino}-3-nitrobenzenesulfonyl)benzamide

IUPAC Traditional name

4-(4-{[2-(4-chlorophenyl)phenyl]methyl}piperazin-1-yl)-N-(4-{[(2R)-4-(dimethylamino)-1-(phenylsulfanyl)butan-2-yl]amino}-3-nitrobenzenesulfonyl)benzamide

Synonyms

ABT-737ABT 7374-[4-[(4’-Chloro[1,1’-biphenyl]-2-yl)methyl]-1-piperazinyl]-N-[[4-[[(1R)-3-(dimethylamino)-1-[(phenylthio)methyl]propyl]amino]-3-nitrophenyl]sulfonyl]benzamide

Registration numbers

CAS Number

852808-04-9

PubChem CID

11228183

PubChem SID

162037377

Properties

Product Information

Salt Data

Free Base

Certificate of Analysis

Download link

Physical Property

Solubility

DMSO

Methanol

Melting Point

152-154°C

Apperance

Yellow Solid

Pharmacology Properties

Target

Bcl-2

Safety Information

Storage Condition

-20°C

-20°C Freezer

MSDS Link

Download link

Molecule Details

Selleck Chemicals

S1002

Research Area

Description

Cancer

Protocol

Kinase Assay ^[1]

Fluorescence polarization assays

Cell Assay ^[4]

Cell Lines

SCLC cell lines NCI-H889, NCI-H1963, NCI-H1417, NCI-H146, NCI-187, DMS79, NCI-1048, NCI-H82, NCI-H196, H69AR, and DMS114

Concentrations

0.001-10 μM

Incubation Time

48 hours

Methods

Animal Study ^[1]

Animal Models

Scid mice injected with Luc-expressing FD/ΔRaf-1:ER cells

Formulation

1 g/mL stock solution of ABT-737 in DMSO is added to a mixture of 30% propylene glycol, 5% Tween 80, 65% D5W (5% dextrose in water) (pH 4?5; final concentration of DMSO ≤ 1%)

Doses

20 and 30 mg/kg

Administration

For intraperitoneal (i.p.) every day