Nsc66811 Chemical Properties

Melting point:

143.0 to 147.0 °C

Boiling point:

529.5±45.0 °C(Predicted)

Density 

1.235±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,2-8°C

solubility 

Soluble in DMSO (up to 25 mg/ml).

pka

4.42±0.50(Predicted)

form 

solid

color 

White

λmax

250nm(EtOH)(lit.)

Stability:

Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 3 months.

InChI

1S/C23H20N2O/c1-16-12-13-18-14-15-20(23(26)22(18)24-16)21(17-8-4-2-5-9-17)25-19-10-6-3-7-11-19/h2-15,21,25-26H,1H3

InChIKey

WEENRMPCSWFMTE-UHFFFAOYSA-N

Safety Information

WGK Germany 

WGK 1

HS Code 

2933.49.7000

Storage Class

11 - Combustible Solids

Nsc66811 Usage And Synthesis

Description

NSC 66811 (6964-62-1) is a novel inhibitor of the MDM2-p53 interaction. Mimics three p53 residues involved in binding to MDM2. NSC-66811 binds to MDM2 with a Ki of 120 nM. Activates p53 in cancer cells. Cell permeable.

Uses

NSC 66811 is a novel inhibitor of the murine double minute 2 (MDM2)-p53 interaction. NSC 66811 activates p53 in colon cancer cells.

Synthesis

GENERAL STEPS: Aniline (0.465 g, 5.0 mmol) and benzaldehyde (0.53 g, 5.0 mmol) were dissolved in ethanol (10 mL) and stirred at room temperature for 5 minutes. Subsequently, 8-hydroxyquinaldine (0.795 g, 5.0 mmol) and a catalytic amount of pyridine (2 drops) were added to the reaction system, and the mixture was heated to 100 °C for 24 h at reflux. The reaction process was monitored by thin layer chromatography (TLC, unfolding agent ratio acetonitrile:water = 3:2) and liquid chromatography-mass spectrometry (LC-MS). After completion of the reaction, the solvent ethanol was removed by rotary evaporator to obtain the crude product. The crude product was purified by fast column chromatography with the eluent being hexane solution containing 2% ethyl acetate. The fraction containing the target compound was collected and allowed to stand overnight in a fume hood to afford the needle-like crystal product 2-methyl-7-(phenyl(phenylamino)methyl)quinolin-8-ol (0.92 g, 54% yield). The structure of the product was confirmed by 1H NMR, 13C NMR, high resolution mass spectrometry (HRMS-ESI) and elemental analysis.1H NMR (500 MHz, CDCl3, δ): 7.97 (d, J = 8.4 Hz, 1H), 7.51 (d, J = 8.5 Hz, 1H), 7.48 (m, 2H), 7.31 (m, 2H), 7.24 (m, 3H), 7.10 (m, 3H), 7.10 (m, 3H), 7.11 (m, 3H), 7.11 (m, 3H). 3H), 7.10 (m, 2H), 6.67 (m, 1H), 6.63 (m, 2H), 6.12 (d, J = 3.4 Hz, 1H), 4.49 (s, 1H), 2.69 (s, 3H); 13C NMR (125 MHz, CDCl3, δ): 157.3, 148.6, 147.7, 142.8, 137.8 , 136.2, 129.3, 128.8, 127.6, 127.4, 125.8, 125.7, 124.2, 122.7, 117.86, 117.78, 113.8, 57.0, 25.1; HRMS-ESI (m/z): [M-C6H6N]+ calcd for C23H20N2O 248.10754, found 248.10762. Elemental analysis calcd (%) for C23H20N2O: C, 81.15; H, 5.92; N, 8.23; found: C, 80.88; H, 5.89; N, 8.17. HPLC (Method-B) Rt = 2.770 min (>95%). 2.770 min (>95%).

References

[1] YIPIN LU. Discovery of a Nanomolar Inhibitor of the Human Murine Double Minute 2 (MDM2)−p53 Interaction through an Integrated, Virtual Database Screening Strategy[J]. Journal of Medicinal Chemistry, 2006, 49 13: 3759-3762. DOI:10.1021/jm060023+

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