Tilorone dihydrochloride

Base Information

• Chemical Name: Tilorone dihydrochloride
• CAS No.: 27591-69-1
• Deprecated CAS: 33562-94-6,93968-77-5
• Molecular Formula: C25H36Cl2N2O3
• Molecular Weight: 483.478
• Hs Code.: 2922509090
• European Community (EC) Number: 631-065-9
• UNII: BJ507J4LKY
• Wikidata: Q27274704
• NCI Thesaurus Code: C72868
• ChEMBL ID: CHEMBL539581
• Mol file: 27591-69-1.mol

Synonyms:Amiksin;Amixin;Amyxin;Bis DEAE Fluorenone;Bis-DEAE-Fluorenone;Hydrochloride, Tilorone;Tilorone;Tilorone Hydrochloride

Chemical Property of Tilorone dihydrochloride

Chemical Property:

• Appearance/Colour: orange yellow crystal powder
• Vapor Pressure: 3.05E-12mmHg at 25°C
• Melting Point: 230-233 °C
• Boiling Point: 552.3 °C at 760 mmHg
• Flash Point: 287.8 °C
• PSA: 42.01000
• Density: 1.102g/cm3
• LogP: 5.94320
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Methanol (Slightly)
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 12
• Exact Mass: 482.2102984
• Heavy Atom Count: 32
• Complexity: 477

Purity/Quality:

99% ^*data from raw suppliers

Tilorone dihydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38-40
• Safety Statements: 7-22-26-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCN(CC)CCOC1=CC2=C(C=C1)C3=C(C2=O)C=C(C=C3)OCCN(CC)CC.Cl.Cl
• Description: Tilorone is an orally active, antiviral compound that induces interferon production and is reported to have antitumor, anti-inflammatory, and neuroprotective actions. With chronic administration, tilorone induces lysosomal glycosaminoglycan storage, rendering glycosaminoglycans resistant to enzymatic degradation.
• Uses: antiviral Tilorone dihydrochloride is an orally active, interferon-inducing antiviral agent. Tilorone dihydrochloride was used to study the interaction of drugs with synthetic self-complementary DNA by SPR (Surface Plasmon Resonance).

Technology Process of Tilorone dihydrochloride

There total 7 articles about Tilorone dihydrochloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 88.0%

2,7-bis(2-[diethylamino]ethoxy)-9-fluorenone (27591-97-5) → 2,7-bis(2-diethylaminoethoxy)fluoren-9-one dihydrochloride (27591-69-1)

Guidance literature:

With hydrogenchloride; In water; acetone; at 20 ℃; for 2h; pH=3 - 4;

DOI:10.1021/cg3012475

Reference yield: 83.0%

2,7-bis(2-iodoethoxy)fluoren-9-one + diethylamine (109-89-7) → 2,7-bis(2-diethylaminoethoxy)fluoren-9-one dihydrochloride (27591-69-1)

Guidance literature:

2,7-bis(2-iodoethoxy)fluoren-9-one; diethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 120h;

With hydrogenchloride; In 1,4-dioxane;

DOI:10.1016/j.bioorg.2019.01.024

Reference yield:

2-chloro-N,N-diethylethylamine hydrochloride (869-24-9) → 2,7-bis(2-diethylaminoethoxy)fluoren-9-one dihydrochloride (27591-69-1)

Guidance literature:

Multi-step reaction with 2 steps

1: NaOH; tetrabutyl-ammonium iodide / H₂O; toluene / 6 h / 80 °C

2: 0.241 g / HCl / propan-2-ol; acetone / pH 3.0

With hydrogenchloride; sodium hydroxide; tetra-(n-butyl)ammonium iodide; In water; isopropyl alcohol; acetone; toluene;

DOI:10.1023/A:1021274913894

upstream raw materials:

2,7-bis(2-[diethylamino]ethoxy)-9-fluorenone

isopropyl alcohol

2-chloro-N,N-diethylethylamine hydrochloride

2-(Diethylamino)ethanol

Downstream raw materials:

C₃₇H₅₂N₄O₅⁽²⁺⁾*2I^(1-)

C₃₄H₄₅N₅O₄⁽²⁺⁾*2I^(1-)

{2-[7-(2-Diethylamino-ethoxy)-9-oxo-9H-fluoren-2-yloxy]-ethyl}-diethyl-methyl-ammonium; iodide

2,7-bis(2-[diethylamino]ethoxy)-9-fluorenone

Refernces

• 1、 Zhang, Junren,Yao, Qizheng,Liu, Zuliang,De Sousa, Maria Emília. "An effective synthesis method for tilorone dihydrochloride with obvious IFN-α inducing activity". . p. 21458 - 21463. Retrieved 2015.
• 2、 Karpinchik,Mal'tsev,Sumrii. "3H2-amyxin synthesis and isolation from biological substrates". . p. 448 - 450. Retrieved 2007/10/03.