structure of 4H-1-Benzopyran-4-one, 2-[2-chloro-4-(trifluoromethyl)phenyl]-5,7-dihydroxy-8-[(2R,3S)-2-(hydroxymethyl)-1-methyl-3-pyrrolidinyl]-, hydrochloride (1:1)

4H-1-Benzopyran-4-one, 2-[2-chloro-4-(trifluoromethyl)phenyl]-5,7-dihydroxy-8-[(2R,3S)-2-(hydroxymethyl)-1-methyl-3-pyrrolidinyl]-, hydrochloride (1:1)

CAS No.: 1000023-05-1
M. Wt: 506.30
M. Fa: C22H20Cl2F3NO5
InChI Key: QCWRANLELLMJSH-UHFFFAOYSA-N

Names and Identifiers of 1000023-05-1

CAS Number

1000023-05-1

IUPAC Name

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

InChI

InChI=1S/C22H19ClF3NO5.ClH/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;1H

InChIKey

QCWRANLELLMJSH-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.Cl

Physical and chemical properties of 1000023-05-1

Exact Mass

505.06700

LogP

5.06330

Molecular Formula

C22H20Cl2F3NO5

Molecular Weight

506.30

PSA

94.14000

Applications of 1000023-05-1

Voruciclib hydrochloride is primarily being explored for its applications in oncology, specifically:

  • Cancer Treatment: Targeting malignancies such as diffuse large B-cell lymphoma and melanoma.
  • Combination Therapy: Enhancing the efficacy of existing chemotherapeutics by overcoming drug resistance mechanisms.
  • Research Tool: Used in preclinical studies to explore CDK inhibition and associated signaling pathways.

Interaction Studies of 1000023-05-1

Voruciclib's interactions with various proteins have been extensively studied. Notably, it has been shown to interact with:

  • ABCB1 and ABCG2 Transporters: Voruciclib increases intracellular drug levels by inhibiting these efflux pumps.
  • CDK Family Members: Its selectivity for CDK9 over other CDKs enhances its therapeutic potential while minimizing off-target effects.
  • Mechanistic Studies: Various assays have demonstrated its ability to alter ATPase activity in transporters without affecting their expression levels.

Biological Activity of 1000023-05-1

Voruciclib exhibits significant biological activity as an inhibitor of CDK9, leading to apoptosis in cancer cells. It has been shown to enhance the effectiveness of other chemotherapeutic agents, such as paclitaxel and doxorubicin, particularly in cells overexpressing ATP-binding cassette transporters like ABCB1 and ABCG2. This synergistic effect is attributed to voruciclib's ability to increase intracellular drug accumulation while decreasing efflux mediated by these transporters. Additionally, voruciclib has been found to modulate various signaling pathways that are critical for cell proliferation and survival.