6533b7d3fe1ef96bd126027b
RESEARCH PRODUCT
Regioselective substitution of 6,7-dichloroquinoline-5,8-dione: synthesis and X-ray crystal structure of 4a,10,11-triazabenzo[3,2-a]fluorene-5,6-diones
Hyun Jung LeeSoyoung ParkDieter SchollmeyerYoung-shin KimMyung-eun Suhsubject
StereochemistryClinical BiochemistryPharmaceutical ScienceAntineoplastic AgentsCrystallography X-RayBiochemistryMedicinal chemistryChemical synthesisInhibitory Concentration 50chemistry.chemical_compoundNucleophilic aromatic substitutionDrug DiscoveryTumor Cells CulturedNucleophilic substitutionHumansMolecular BiologySubstitution reactionFluorenesMolecular StructureOrganic ChemistryQuinonesRegioselectivityStereoisomerismQuinonechemistryDoxorubicinEthyl acetoacetateQuinolinesMolecular MedicineAcid hydrolysisDrug Screening Assays Antitumordescription
6,7-Dichloroquinoline-5,8-dione (1) was reacted with a number of 2-aminopyridine derivatives. Of the several possible products of this reaction, 4a,10,11-triazabenzo[3,2-a]fluorene-5,6-dione (6), produced by condensation and rearrangement, was obtained as the major product, and its structure was subsequently unambigously determined by X-ray crystallographic study. Ortho-quinones were produced via nucleophilic substitution at position C7, which was unexpected, considering that para-quinones were produced via C6 substitution in the reaction between compound 1 and ethyl acetoacetate in our previous work. Such unexpected nucleophilic substitution at C7 provides an effective, yet simple route, to the preparation of biologically active ortho-quinone derivatives.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2003-04-01 | Bioorganic & Medicinal Chemistry |