27591-97-5

Basic information

• Product Name: Tilorone
• Synonyms: Tilorone;2,7-Bis[2-(diethylamino)ethoxy]-9-fluorenone;2,7-Bis[2-(diethylamino)ethoxy]-9H-fluoren-9-one;Bis-DEAE-fluorenone;2,7-bis[2-(diethylamino)ethoxy]fluoren-9-one
• CAS NO: 27591-97-5
• Molecular Formula: C₂₅H₃₄N₂O₃
• Molecular Weight: 410.55
• EINECS: 1806241-263-5
• Mol File: 27591-97-5.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 552.3 °C at 760 mmHg
• Flash Point: 287.8 °C
• Appearance: /
• Density: 1.102 g/cm³
• Vapor Pressure: 3.05E-12mmHg at 25°C
• Refractive Index: 1.563
• PKA: 9.67±0.25(Predicted)
• CAS DataBase Reference: Tilorone(CAS DataBase Reference)
• NIST Chemistry Reference: Tilorone(27591-97-5)
• EPA Substance Registry System: Tilorone(27591-97-5)

Safety Data

• Hazardous Substances Data: 27591-97-5(Hazardous Substances Data)

Usage

General Description

Tilorone is a synthetic small molecule with antiviral and immunomodulatory properties. It has been studied for its potential to treat various viral infections, including influenza, herpes, and HIV. Tilorone has been found to work by stimulating the production of interferons, which are proteins that help the immune system fight off infections. In addition to its antiviral effects, Tilorone has also been shown to have anti-inflammatory properties, making it a promising candidate for the treatment of viral diseases with an inflammatory component. Research on Tilorone is ongoing, and it may hold potential for the development of new antiviral therapies.

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

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

Downstream Products

• 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 
• 27591-69-1 2,7-bis(2-diethylaminoethoxy)fluoren-9-one dihydrochloride 
• 54196-27-9 3,8-Bis[(β-Diethylamino)ethoxy]-6-Benzylaminophenanthridine 
• 93418-61-2 C₃₇H₅₂N₄O₅⁽²⁺⁾*2I^(1-) 
• 93444-41-8 C₃₄H₄₅N₅O₄⁽²⁺⁾*2I^(1-) 
• 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 

Relevant articles and documents

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.

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.

3H2-amyxin synthesis and isolation from biological substrates

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