86456-22-6

Usage

Uses

Used in Pharmaceutical Formulations:
8-[2-(dimethylamino)ethyl]amino-5-(hydroxymethyl)-9-oxo-9H-xanthen-2-yl 4-methylbenzenesulfonate is used as a counterion in pharmaceutical formulations for its ability to stabilize and enhance the solubility of active pharmaceutical ingredients.
Used in Drug Delivery Systems:
In the pharmaceutical industry, 8-[2-(dimethylamino)ethyl]amino-5-(hydroxymethyl)-9-oxo-9H-xanthen-2-yl 4-methylbenzenesulfonate is utilized as a component in drug delivery systems to improve the bioavailability and targeted delivery of therapeutic agents, potentially enhancing their efficacy and reducing side effects.
Used in Chemical Research:
8-[2-(dimethylamino)ethyl]amino-5-(hydroxymethyl)-9-oxo-9H-xanthen-2-yl 4-methylbenzenesulfonate serves as a subject of chemical research for its unique structure and properties, which may lead to the discovery of new applications and insights into its behavior in various chemical processes.
While the specific uses of 8-{[2-(dimethylamino)ethyl]amino}-5-(hydroxymethyl)-9-oxo-9H-xanthen-2-yl 4-methylbenzenesulfonate in different industries are still under investigation, its presence in the field of chemistry and pharmaceuticals highlights its potential for diverse applications, pending further research and development.

Synthetic route

formaldehyd (50-00-0) + 1-<<2-(dimethylamino)ethyl>amino>-7-(toluenesulfonyloxy)-9H-xanthen-9-one (86456-20-4) → NSC 354677 (86456-22-6)

Conditions	Yield
With acetic acid at 70℃; for 72h;	46%

3-iodochlorobenzene (625-99-0) → NSC 354677 (86456-22-6)

Conditions	Yield
Multi-step reaction with 5 steps 1: 1.) K2CO3, 2.) Cu, CuI / 1.) DMF, 120 deg C, 10 min, 2.) DMF, reflux, 50 h 2: 1.) 50percent polyphosphoric acid, 2.) pyridine / 1.) 120 deg C, 3 h, 2.) reflux, 16 h 3: 87 percent / 56percent HI / 4 h / Heating 4: 92 percent / pyridine / 1.5 h / 50 °C 5: 46 percent / 5 N aq. acetic acid / 72 h / 70 °C View Scheme

5-methoxysalicylic acid (2612-02-4) → NSC 354677 (86456-22-6)

Conditions	Yield
Multi-step reaction with 5 steps 1: 1.) K2CO3, 2.) Cu, CuI / 1.) DMF, 120 deg C, 10 min, 2.) DMF, reflux, 50 h 2: 1.) 50percent polyphosphoric acid, 2.) pyridine / 1.) 120 deg C, 3 h, 2.) reflux, 16 h 3: 87 percent / 56percent HI / 4 h / Heating 4: 92 percent / pyridine / 1.5 h / 50 °C 5: 46 percent / 5 N aq. acetic acid / 72 h / 70 °C View Scheme

2-(3-chlorophenoxy)-5-methoxybenzoic acid (86456-12-4) → NSC 354677 (86456-22-6)

Conditions	Yield
Multi-step reaction with 4 steps 1: 1.) 50percent polyphosphoric acid, 2.) pyridine / 1.) 120 deg C, 3 h, 2.) reflux, 16 h 2: 87 percent / 56percent HI / 4 h / Heating 3: 92 percent / pyridine / 1.5 h / 50 °C 4: 46 percent / 5 N aq. acetic acid / 72 h / 70 °C View Scheme

1-<<2-(dimethylamino)ethyl>amino>-7-hydroxy-9H-xanthen-9-one (86456-18-0) → NSC 354677 (86456-22-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 92 percent / pyridine / 1.5 h / 50 °C 2: 46 percent / 5 N aq. acetic acid / 72 h / 70 °C View Scheme

1-<<2-(dimethylamino)ethyl>amino>-7-methoxy-9H-xanthen-9-one (86456-16-8) → NSC 354677 (86456-22-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: 87 percent / 56percent HI / 4 h / Heating 2: 92 percent / pyridine / 1.5 h / 50 °C 3: 46 percent / 5 N aq. acetic acid / 72 h / 70 °C View Scheme

NSC 354677 (86456-22-6) → 1-[[2-(Dimethylamino)ethyl]amino]-7-hydroxy-4-(hydroxymethyl)-9H-xanthen-9-one (86455-98-3)

Conditions	Yield
With potassium hydroxide In ethanol for 0.5h; Heating;	88%

Upstream product

• 625-99-0 3-iodochlorobenzene 
• 86456-16-8 1-<<2-(dimethylamino)ethyl>amino>-7-methoxy-9H-xanthen-9-one 
• 86456-18-0 1-<<2-(dimethylamino)ethyl>amino>-7-hydroxy-9H-xanthen-9-one 
• 86456-12-4 2-(3-chlorophenoxy)-5-methoxybenzoic acid 
• 2612-02-4 5-methoxysalicylic acid 
• 50-00-0 formaldehyd 
• 86456-20-4 1-<<2-(dimethylamino)ethyl>amino>-7-(toluenesulfonyloxy)-9H-xanthen-9-one 

Downstream Products

• 86455-98-3 1-[[2-(Dimethylamino)ethyl]amino]-7-hydroxy-4-(hydroxymethyl)-9H-xanthen-9-one 

Relevant academic research and scientific papers

7-Hydroxylucanthone, 7-hydroxhycanthone and their analogs

7-Hydroxylucanthone and 7-hydroxyhycanthone derivatives have been found to have significant antitumor effect. The derivatives are of the general formula: STR1 wherein the radicals R1 and R2 are lower alkyl groups or other simple groups and R3 is OH where X=O, and H or OH where X=S.

Analogues of hycanthone and lucanthone as antitumor agents

Hycanthone analogues (5 and 6) containing 7-substituted hydroxyl groups were prepared and evaluated as antitumor agents. These compounds were significantly more active than the corresponding unsubtituted derivatives. The 7-hydroxylated-4-(hydroxymethyl)-9H-xanthen-9-ones, 11 and 12, were also active antitumor agents. However, the 7-hydroxy-9H-xanthen-9-one counterparts of the 7-hydroxylucanthones were totally devoid of antitumor activity. Results obtained thus far are consistent with the hypothesis that 4-hydroxymethyl substituents in the 9H-xanthen-9-one and 9H-thioxanthen-9-one series are required for antitumor activity.