35897-82-6

Upstream product

• 102-92-1 Cinnamoyl chloride 
• 7465-58-9 9-hydroxy-1-oxophenalene 
• 74-88-4 methyl iodide 
• 313509-54-5 9-methoxy-2,3-dihydro-1H-phenalen-1-one 
• 93-04-9 2-Methoxynaphthalene 

Relevant academic research and scientific papers

A Green-Absorbing, Red-Fluorescent Phenalenone-Based Photosensitizer as a Theranostic Agent for Photodynamic Therapy

Phenalenone is a synthetically accessible, highly efficient photosensitizer with a near-unity singlet oxygen quantum yield. Unfortunately, its UV absorption and lack of fluorescence has made it unsuitable for fluorescence-guided photodynamic therapy against cancer. In this work, we synthesized a series of phenalenone derivatives containing electron-donating groups to red-shift the absorption spectrum and bromine(s) to permit good singlet oxygen production via the heavy-atom effect. Of the derivatives synthesized, the phenalenone containing an amine at the 6-position with bromines at the 2- and 5-positions (OE19) exhibited the longest absorption wavelength (i.e., green) and produced both singlet oxygen and red fluorescence efficiently. OE19 induced photocytotoxicity with nanomolar potency in 2D cultured PANC-1 cancer cells as well as light-induced destruction of PANC-1 spheroids with minimal dark toxicity. Overall, OE19 opens up the possibility of employing phenalenone-based photosensitizers as theranostic agents for photodynamic cancer therapy.

Synthesis of 8-phenylphenalenones: 2-hydroxy-8-(4-hydroxyphenyl)-1h-phenalen-1-one from eichhornia crassipes

2-Hydroxy-8-(4-hydroxyphenyl)-1H-phenalen-1-one (1), the first reported 8-phenylphenalenone from the roots of Eichhornia crassipes (water hyacinth), was synthesized starting from 2-methoxynaphthalene in 11 steps and with an overall yield of 2%. A cascade Friedel-Crafts/Michael annulation reaction between acryloyl chloride and 2-methoxynaphthalene afforded 9-methoxyperinaphthanone that, after transformation to 9-methoxy-2-(4-methoxyphenyl)-1H-phenalen-1-one by means of standard Suzuki-Miyaura methodology, was subjected to a reductive carbonyl transposition to afford 8-(4-methoxyphenyl)perinaphthanone. Dehydrogenation, epoxidation, and demethylation of the latter afforded 1.

Ligand mixed-valence and electrical conductivity in coordination complexes containing a redox-active phenalenol-substituted ligand

A new redox-active hydrazone ligand bearing a phenalenol group is described (phpl), which produces neutral six-coordinate Fe and Co complexes (1 & 2) with the ligands identified in different oxidation states; an open-shell anion radical and closed-shell dianion. An intense and very low-energy intervalence charge transfer (IVCT) band is identified in solid-state and in solution in the complexes. Single crystals of 1 are semiconducting (at 300 K, σ = 3.05 × 10-4 S cm-1 with Ea = 245 meV).

FLUORESCENT ANTICANCER PLATINUM DRUGS

The present disclosure is in relation to the field of nanotechnology and cancer therapeutics. In particular, the present disclosure relates to fluorescent platinum based compounds. The disclosure further relates to synthesis of said fluorescent platinum based compounds, nanoparticles and compositions comprising said fluorescent platinum based compounds/nanoparticles. The disclosure also relates to methods of managing cancer by the fluorescence changes between aforesaid platinum based compounds and corresponding free ligands, nanoparticles and compositions.

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.