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CAS No.: 1000023-04-0
M. Wt: 469.83800
M. Fa: C22H19ClF3NO5
InChI Key: MRPGRAKIAJJGMM-UHFFFAOYSA-N
Appearance: Yellow Solid

Names and Identifiers of 1000023-04-0

CAS Number

1000023-04-0

MDL Number

MFCD28386202

IUPAC Name

2-[2-chloro-4-(trifluoromethyl)phenyl]-5,7-dihydroxy-8-[2-(hydroxymethyl)-1-methylpyrrolidin-3-yl]chromen-4-one

InChI

InChI=1S/C22H19ClF3NO5/c1-27-5-4-12(14(27)9-28)19-15(29)7-16(30)20-17(31)8-18(32-21(19)20)11-3-2-10(6-13(11)23)22(24,25)26/h2-3,6-8,12,14,28-30H,4-5,9H2,1H3

InChIKey

MRPGRAKIAJJGMM-UHFFFAOYSA-N

Canonical SMILES

CN1CCC(C1CO)C2=C(C=C(C3=C2OC(=CC3=O)C4=C(C=C(C=C4)C(F)(F)F)Cl)O)O

UNSPSC Code

12352100

Physical and chemical properties of 1000023-04-0

Acidity coefficient

6.36±0.40(Predicted)

Boiling Point

587.6±50.0 °C(Predicted)

Density

1.493±0.06 g/cm3(Predicted)

Exact Mass

469.09000

H Bond Acceptors

6

H Bond Donors

3

LogP

4.26130

Molecular Formula

C22H19ClF3NO5

Molecular Weight

469.83800

PSA

94.14000

Safety Information of 1000023-04-0

Pictograms

Signal Word

 Warning

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

Applications of 1000023-04-0

Voruciclib is primarily being explored for its applications in oncology. Its main therapeutic focus includes:

  • Melanoma Treatment: Particularly effective against BRAF-mutant melanoma.
  • Combination Therapies: Used in conjunction with other agents like BRAF inhibitors and venetoclax for enhanced anti-cancer effects.

Interaction Studies of 1000023-04-0

Voruciclib has been studied for its interactions with various proteins involved in drug resistance mechanisms:

  • ABCB1 and ABCG2 Proteins: Voruciclib enhances the accumulation of chemotherapeutic agents by inhibiting the efflux functions of these transporters. This effect was confirmed through assays measuring drug accumulation in resistant cell lines.
  • Synergistic Effects: Studies indicate that voruciclib can synergize with other drugs, leading to increased apoptosis rates in cancer cells.

Biological Activity of 1000023-04-0

Voruciclib exhibits significant biological activity as a CDK4/6 inhibitor. It has been shown to induce cell cycle arrest and apoptosis in various cancer cell lines, including those resistant to standard therapies. The compound has demonstrated synergy with other chemotherapeutics, such as venetoclax, enhancing their effectiveness against acute myeloid leukemia (AML) cells by downregulating MCL-1 and c-Myc proteins.

Mechanisms of Action:
  • Inhibition of CDK9: Voruciclib suppresses CDK9 activity, which is crucial for the transcriptional regulation of anti-apoptotic proteins.
  • Chemo-sensitization: It enhances the efficacy of other chemotherapeutics by increasing the intracellular accumulation of drugs like paclitaxel and doxorubicin in resistant cancer cells.