6533b7dafe1ef96bd126d9a8

RESEARCH PRODUCT

Synthesis and antiproliferative activity of triazenoindazoles and triazenopyrazoles: a comparative study.

Benedetta MaggioGiuseppe DaidoneDemetrio RaffaFabiana PlesciaMaria Valeria RaimondiDomenico Schillaci

subject

IndazolesMagnetic Resonance SpectroscopyHL60StereochemistryAntineoplastic AgentsMedicinal chemistryChemical synthesisPyrrolidinechemistry.chemical_compoundInhibitory Concentration 50Structure-Activity RelationshipDrug DiscoveryTumor Cells CulturedMoietyHumansTriazeneBenzeneDimethylaminePharmacologyDiethylamineIndazoleBicyclic moleculeMolecular StructureOrganic ChemistryGeneral MedicineSettore CHIM/08 - Chimica FarmaceuticachemistryPyrazolesTriazenoindazoles Triazenopyrazoles Antiproliferative activity Hindered rotationDrug Screening Assays AntitumorTriazenesCell Division

description

Several triazenoindazoles and triazenopyrazoles were prepared transforming the appropriate aminoindazoles and aminopyrazoles in the corresponding diazonium salts which were reacted with dimethylamine, diethylamine and pyrrolidine. All the triazenes were tested for their antiproliferative activity against K562, HL60, L1210 and MCF7 cell lines. The biological data showed that the benzocondensation plays a positive role on the antiproliferative activity. The (1)H-NMR spectra showed that the rotational barrier around the N(2)-N(3) bond in the triazene group can be influenced both by the position of this group in the indazole nucleus and by the substitution pattern in the benzene moiety.

yearjournalcountryeditionlanguage
2003-07-30European journal of medicinal chemistry
10.1016/j.ejmech.2003.11.012https://pubmed.ncbi.nlm.nih.gov/15051169