69454-54-2

Usage

InChI:InChI=1/C14H11NO/c1-15-11-7-5-9-3-2-4-10-6-8-12(16)14(11)13(9)10/h2-8,15H,1H3

Upstream product

• 7465-58-9 9-hydroxy-1-oxophenalene 
• 74-89-5 methylamine 

Downstream Products

• 67618-28-4 9-methylamino-1-methyliminophenalene 

Relevant academic research and scientific papers

A safe and efficacious Pt(ii) anticancer prodrug: Design, synthesis,: In vitro efficacy, the role of carrier ligands and in vivo tumour growth inhibition

Diaminocyclohexane-Pt(ii)-phenalenyl complexes (1 and 2) showed an appropriate balance between efficacy and toxicity. Compound 2 showed nearly two-fold higher tumour growth inhibition than oxaliplatin in a murine NSCLC tumour model, when a combined drug development approach was used. The fluorescent properties of phenalenone were utilized to understand the mechanistic details of the drug.

Direct Amination of 9-Hydroxy-1-oxophenalene to Produce 9-Amino-1-oxophenalene and Related Compounds

In connection with our studies of organo-non-metallic complexes of the 1,9-disubstituted phenalene unit 1 we required access to compounds possessing a total of just two ionizable hydrogen atoms in the A,B groups of 1.The prototypical compound in this series, 9-amino-1-oxophenalene (2), is not known although 9-hydroxy-1-oxophenalene (3) was first prepared in 1941 and a number of derivatives of 1 possessing one or three ionizable hydrogen atoms in the A,B groups have recently become available.We have found that the high-pressure reaction between 9-hydroxy-1-oxophenalene (3) and aqueous ammonia affords the desired 9-amino-1-oxophenalene (2) in high yield and good purity under relatively mild conditions.In addition 2 may be alkylated to produce the 9-amino-1-ethoxyphenalenylium salt which serves as a precursor for the other derivatives in this series with two ionizable hydrogen atoms in the A,B groups of 1.

1,9-Disubstituted phenalenes-I. Synthesis of n- and s-derivatives of 9-hydroxy-1-phenalenone

The reaction of 9-hydroxy-1-phenalenone with Ag2O and alkyliodides gives the analogous β-keto-ethers from which synthetic pathways have been devised to isolate and characterise some nitrogen and sulphur derivatives. As intermediates stable phenalenium cations can be isolated by the reaction of 9-substituted 1-phenalenones with [(C2H5)3O]+BF4-. Whenever possible, a strong intramolecular H-bond is formed between the 1-and 9-substituents as shown by the low-field resonances of the respective hydrogens in the 1H NMR and the stability of the compounds towards reduction.