voruciclib   

GtoPdb Ligand ID: 9923

Synonyms: P1446A | P1446A-05
Compound class: Synthetic organic
Comment: Voruciclib (P1446A, or P1446A-05) is an orally active, non-selective CDK inhibitor that was developed for antineoplastic potential. Potent inhibition of CDK9, 4/6 and 1 by voruciclib is considered as a novel pro-apoptotic mechanism applicable to the treatment of malignant melanoma [3] and to overcome resistance to Bcl-2 inhibition (e.g. by venetoclax) in B cell malignancies [2,4].
Use of voruciclib in combination with BRAF inhibitors for the treatment of malignant melanoma is claimed in patent US20160136132A1 [1]. Preparation of pure (+)-trans enantiomer of the compound shown here, is claimed in patent WO2007148158A1 [5].
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 3
Hydrogen bond donors 3
Rotatable bonds 4
Topological polar surface area 94.14
Molecular weight 469.09
XLogP 4.88
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES OCC1N(C)CCC1c1c(O)cc(c2c1oc(cc2=O)c1ccc(cc1Cl)C(F)(F)F)O
Isomeric SMILES OC[C@@H]1N(C)CC[C@H]1c1c(O)cc(c2c1oc(cc2=O)c1ccc(cc1Cl)C(F)(F)F)O
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/t12-,14+/m1/s1
InChI Key MRPGRAKIAJJGMM-OCCSQVGLSA-N
Classification
Compound class Synthetic organic
IUPAC Name
2-[2-chloro-4-(trifluoromethyl)phenyl]-5,7-dihydroxy-8-[(2R,3S)-2-(hydroxymethyl)-1-methylpyrrolidin-3-yl]chromen-4-one
International Nonproprietary Names
INN number INN
9791 voruciclib
Synonyms
P1446A | P1446A-05
Database Links
CAS Registry No. 1000023-04-0 (source: WHO INN record)
GtoPdb PubChem SID 363894217
PubChem CID 67409219
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