4,6-DICHLORO-1H-INDOLE-2,3-DIONE Chemical Properties

Melting point:

260.5-261℃

Density 

1.643±0.06 g/cm3 (20 ºC 760 Torr)

storage temp. 

Sealed in dry,Room Temperature

pka

8.59±0.20(Predicted)

form 

Solid

color 

Light yellow to yellow

InChI

InChI=1S/C8H3Cl2NO2/c9-3-1-4(10)6-5(2-3)11-8(13)7(6)12/h1-2H,(H,11,12,13)

InChIKey

CGCVHJCZBIYRQC-UHFFFAOYSA-N

SMILES

N1C2=C(C(Cl)=CC(Cl)=C2)C(=O)C1=O

Safety Information

RIDADR 

UN2811

HazardClass 

6.1

4,6-DICHLORO-1H-INDOLE-2,3-DIONE Usage And Synthesis

Chemical Properties

Yellow powder

Uses

CFL-120 is a potent KRasG12C inhibitor. CFL-120 shows an antiproliferative effect. CFL-120 shows anticancer activity. CFL-120 has the potential for the research of lung cancer[1].

Synthesis

General procedure for the synthesis of 4,6-dichlorodihydroindole-2,3-dione from 2-hydroxyimino-N-(3,5-dichlorophenyl)-acetamide: 1. Preparation of intermediate I-2: Intermediate I-1 (10.0 g, 42.9 mmol) prepared above was slowly added to concentrated hydrochloric acid. Under ice bath conditions, sulfuric acid (50 mL) was added to ensure that the temperature of the reaction mixture was kept below 50 °C. 2. After the reaction was complete, the dark colored solution was heated at 90 °C for 10 min. 3. The reaction mixture was cooled to room temperature and then poured into 10 times the volume of ice and stirred vigorously for 1 hour. 4. The insoluble solid formed was collected, washed with water and dried under vacuum to give 4,6-dichlorodihydroindole-2,3-dione (8.90 g, 96% yield) as an orange solid. - TLC Rf = 0.4 (EtOAc:hexane=1:3) - Melting point: 228-230°C - 1H NMR (DMSO-d6) δ: 6.97 (d, J=1.8Hz, 1H, ArH), 7.32 (d, J=1.8Hz, 1H, ArH), 11.42 (br s, 1H, NH) - MS (EI) m/e: 216 [M+], 188 [M+-CO2], 160.

in vivo

IC 50

KRAS(G12C)

References

[1] Orgován Z, et al. Covalent fragment mapping of KRasG12C revealed novel chemotypes with in vivo potency. Eur J Med Chem. 2023 Mar 15;250:115212. DOI:10.1016/j.ejmech.2023.115212

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