27591-97-5

Usage

Uses

Used in Pharmaceutical Industry:
Tilorone is used as an antiviral agent for its ability to combat various viral infections such as influenza, herpes, and HIV. Its mechanism involves the stimulation of interferon production, which aids the immune system in fighting off these infections.
Used in Immunotherapy:
Tilorone is utilized as an immunomodulatory agent due to its capacity to regulate the immune response, making it a potential candidate for the treatment of viral diseases that have an inflammatory component.
Used in Drug Development:
Tilorone is considered in the development of new antiviral therapies, given its ongoing research and potential to contribute to innovative treatments for viral infections.

InChI:InChI=1/C25H34N2O3/c1-5-26(6-2)13-15-29-19-9-11-21-22-12-10-20(30-16-14-27(7-3)8-4)18-24(22)25(28)23(21)17-19/h9-12,17-18H,5-8,13-16H2,1-4H3

Upstream product

• 31551-45-8 2,7-dinitro-9-fluorenone 
• 53134-09-1 2,7-diacetoxy-fluorene 
• 696-62-8 para-iodoanisole 
• 591-31-1 3-methoxy-benzaldehyde 
• 13354-15-9 9H-fluorene-2,7-disulfonic acid dipotassium salt 
• 86-73-7 9H-fluorene 
• 53197-57-2 4,4'-dihydroxy-[1,1'-biphenyl]-2-carboxylic acid 
• 2915-84-6 2,7-diaminofluoren-9-one 
• 100-37-8 2-(Diethylamino)ethanol 
• 1010786-65-8 4,4'-bis-(2-diethylamino-ethoxy)-biphenyl-2-carboxylic acid methyl ester 
• 869-24-9 2-chloro-N,N-diethylethylamine hydrochloride 
• 53133-99-6 9-oxo-9H-fluorene-2,7-diyl diacetate 
• 42523-29-5 2,7-dihydroxy-9H-fluoren-9-one 
• 27591-69-1 2,7-bis(2-diethylaminoethoxy)fluoren-9-one dihydrochloride 

Downstream Products

• 93418-47-4 {2-[7-(2-Diethylamino-ethoxy)-9-oxo-9H-fluoren-2-yloxy]-ethyl}-diethyl-methyl-ammonium; iodide 
• 93418-44-1 Tiloron-bis-iodmethylat 
• 27591-69-1 2,7-bis(2-diethylaminoethoxy)fluoren-9-one dihydrochloride 
• 54196-27-9 3,8-Bis[(β-Diethylamino)ethoxy]-6-Benzylaminophenanthridine 
• 126070-99-3 2,7-Bis-<2-(Diethylamino)ethoxy>-9H-fluoren 
• 71915-20-3 {2-[9-{[2,7-Bis-(2-diethylamino-ethoxy)-fluoren-9-ylidene]-hydrazono}-7-(2-diethylamino-ethoxy)-9H-fluoren-2-yloxy]-ethyl}-diethyl-amine 
• 959303-73-2 {2-[7-(2-Diethylamino-ethoxy)-9-hydrazono-9H-fluoren-2-yloxy]-ethyl}-diethyl-amine 
• 93418-61-2 C₃₇H₅₂N₄O₅⁽²⁺⁾*2I^(1-) 
• 93444-41-8 C₃₄H₄₅N₅O₄⁽²⁺⁾*2I^(1-) 

Relevant academic research and scientific papers

Synthesis of Fluorenones from Benzaldehydes and Aryl Iodides: Dual C-H Functionalizations Using a Transient Directing Group

The first synthesis of substituted fluorenones directly from benzaldehydes and aryl iodides via a Pd(II)-catalyzed C(sp2)-H functionalization cascade is reported. Featuring anthranilic acid as an inexpensive transient directing group, the process is compatible with a variety of benzaldehydes and aryl iodides. A three-step synthesis of the antiviral drug Tilorone was completed in an excellent overall yield (40%), demonstrating the utility of this method.

Palladium catalyzed domino C-H activation strategy: An access to 9- fluorenones

Palladium catalyzed domino C-H functionalization reaction of arylaldehyde with dihaloarene has been developed to access 9-flourenone molecules. Bidentate ligand assisted strategy, single step reaction, high yield and excellent functional group tolerance make this method concise and effective for the synthesis of 9-flourenone. In addition, proposed method has been successfully employed to synthesise Tilorone in gram scale.

An effective synthesis method for tilorone dihydrochloride with obvious IFN-α inducing activity

Tilorone dihydrochloride (1) has great potential for inducing interferon against pathogenic infection. In this paper, we describe a convenient preparation method for 2,7-dihydroxyfluoren-9-one (2), which is a usual pharmaceutical intermediate for preparing tilorone dihydrochloride (1). In the novel method, methyl esterification of 4,4′-dihydroxy-[1,1′-biphenyl]-2-carboxylic acid (4) was carried out under milder conditions with higher yield and played an important role in the preparation of compound 2. The structures of the relative intermediates and target compound were characterized by melting point, IR, MS, and 1H-NMR. Furthermore, the synthesized tilorone dihydrochloride exhibited an obvious effect on induction of interferon-α (IFN-α) in mice within 12 h, and the peak level was observed until 24 h. This fruitful work has resulted in tilorone dihydrochloride becoming available in large-scale and wide application in clinics, which has a good pharmaceutical development prospects.

Chronobiotic activity of N-[2-(2,7-dimethoxyfluoren-9-yl)ethyl]- propanamide. Synthesis and melatonergic pharmacology of fluoren-9-ylethyl amides

Compound 2b demonstrated full agonism at both human MT1 and MT2 receptors and demonstrated chronobiotic activity in both acute and chronic rat models, producing an acute phase advance of 32 min at 1 mg/kg and chronically entraining free-running rats with a mean effective dose of 0.23 mg/kg. This compound was significantly less efficacious than melatonin in constricting human coronary artery. A series of fluoren-9-yl ethyl amides (2) were synthesized and evaluated for human melatonin MT1 and MT 2 receptor binding. N-[2-(2,7-dimethoxyfluoren-9-yl)ethyl]propanamide (2b) was selected and evaluated in functional assays measuring intrinsic activity at the human MT1 and MT2 receptors and demonstrated full agonism at both receptors. The chronobiotic properties of 2b were demonstrated in both acute and chronic rat models where 2b produced an acute phase advance of 32 min at 1 mg/kg and chronically entrained free-running rats with a mean effective dose of 0.23 mg/kg. Compound 2b is significantly less efficacious than melatonin in constricting human coronary artery.