Tilorone dihydrochloride CAS#: 27591-69-1; 凯望编码 (ChemWhat Code): 122646
Identification
| 英文名 | Tilorone dihydrochloride |
| IUPAC Name | 2,7-bis[2-(diethylamino)ethoxy]fluoren-9-one;dihydrochloride |
| 分子结构 |  |
| CAS编号 | 27591-69-1 |
| EINECS Number | No data available |
| MDL Number | MFCD00134071 |
| Beilstein Registry Number | No data available |
| 别名 | 2,7-bis(2-diethylaminoethoxy)fluoren-9-one dihydrochloride, Tilorone hydrochloride, 2,7-bis<2-(diethylamino)ethoxy>fluoren-9-one dihydrochloride, 2,7-bis-(2-N,N-diethylamino-ethoxy)fluoren-9-one dihydrochloride, 2,7-bis[2-(diethylamino)ethoxy]-9H-fluoren-9-one dihydrochloride, 2,7-bis[2-(diethylamino)ethoxy]-9-fluorenone dihydrochloride, 2,7-bis[2-(diethylamino)ethoxy]fluoren-9-one dihydrochloride;CAS Number: 27591-69-1 |
| 分子式 | C25H34N2O3.2(HCl) |
| 分子量 | 483.47 |
| InChI | InChI=1S/C25H34N2O3.2ClH/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;2*1H |
| InChI Key | BSVYJQAWONIOOU-UHFFFAOYSA-N |
| Canonical SMILES | CCN(CC)CCOC1=CC2=C(C=C1)C3=C(C2=O)C=C(C=C3)OCCN(CC)CC.Cl.Cl |
| Patent Information |
| No data available |
Physical Data
| Appearance | Orange-yellow crystalline powder |
| Solubility | No data available |
| Flash Point | No data available |
| Refractive index | No data available |
| Sensitivity | No data available |
| Melting Point, °C | Solvent (Melting Point) | Comment (Melting Point) |
| 236 – 237 | ||
| 231 – 233 | ethanol | |
| 228 – 232 | ||
| 232 – 234 | propan-2-ol, ethanol | |
| 235 – 236 | propan-2-ol, methanol | Decomposition |
| Density, g·cm-3 | Type (Density) |
| 1.252 | crystallographic |
| 1.256 | crystallographic |
Spectra
| Description (NMR Spectroscopy) | Nucleus (NMR Spectroscopy) | Solvents (NMR Spectroscopy) | Frequency (NMR Spectroscopy), MHz |
| Chemical shifts | 1H | water-d2 | 400 |
| Chemical shifts | 1H |
| Description (IR Spectroscopy) | Solvent (IR Spectroscopy) | Temperature (IR Spectroscopy), °C |
| Bands | potassium bromide | |
| Bands |
| Description (Mass Spectrometry) |
| fast atom bombardment (FAB), spectrum |
| electrospray ionisation (ESI), spectrum |
Route of Synthesis (ROS)
| Conditions | Yield |
| Stage #1: 2,7-bis(2-iodoethoxy)fluoren-9-one; diethylamine In N,N-dimethyl-formamide at 20℃; for 120h; Stage #2: With hydrogenchloride In 1,4-dioxane Experimental Procedure 4.1.8. 2,7-bis[2-(diethylamino)ethoxy]fluoren-9-one dihydrochloride (3a) Diethylamine (0.73 g, 0.01 mol) was added to a solution of 2f(1.10 g 0.002 mol) in DMF (5 mL). The reaction mixture was kept atroom temperature for 5 days, diluted with H2O (200 mL), and thenacidified with HCl to achieve a pH of 2-3. The acidic solution waswashed with CHCl3 (3×50 mL), and then basified with aqueous NaOHuntil pH was 12-13. The product was extracted with CHCl3(3×50 mL). The combined CHCl3 layers were washed with H2O untilpH of aqueous layer was about 7, dried (Na2SO4) and evaporated underreduced pressure. The resultant residue was dissolved in anhydrousdioxane (20 mL) and then saturated anhydrous solution of HCl in dioxanewas added to the resulting solution while stirring. The solventwas evaporated under reduced pressure to give a crude gummy residuethat was suspended in acetone. A stirred suspension was refluxed for15 min, followed by filtration to give a solid material. The procedurewas repeated until a pure reddish solid product (3a) was afforded;(0.80 g, Yield: 83%); mp 236-237 °C (Lit. mp 235 -236 °C [22]; FABMSm/z: M+ = 411. | 83% |
Safety and Hazards
| Pictogram(s) |   |
| Signal | Warning |
| GHS Hazard Statements | H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral] H312 (100%): Harmful in contact with skin [Warning Acute toxicity, dermal] H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation] H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation] H332 (100%): Harmful if inhaled [Warning Acute toxicity, inhalation] H335 (97.56%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation] H351 (97.56%): Suspected of causing cancer [Warning Carcinogenicity] Information may vary between notifications depending on impurities, additives, and other factors. |
| Precautionary Statement Codes | P201, P202, P261, P264, P270, P271, P280, P281, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P308+P313, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P403+P233, P405, and P501 (The corresponding statement to each P-code can be found at the GHS Classification page.) For more detailed information, please visit ECHA C&L website |
Source: European Chemicals Agency (ECHA)
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License URL: https://echa.europa.eu/web/guest/legal-notice
Record Name: (1-Cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylamino-morpholino-carbenium hexafluorophosphate
URL: https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/213446
Description: The information provided here is aggregated from the “Notified classification and labelling” from ECHA’s C&L Inventory. Read more: https://echa.europa.eu/information-on-chemicals/cl-inventory-database
Other Data
| Transportation | NONH for all modes of transport |
| Under the room temperature and away from light | |
| HS Code | 294200 |
| Storage | Under the room temperature and away from light |
| Shelf Life | 1 year |
| Market Price | USD |
| Druglikeness | |
| Lipinski rules component | |
| 分子量 | 483.478 |
| logP | 5.234 |
| HBA | 3 |
| HBD | 0 |
| Matching Lipinski Rules | 3 |
| Veber rules component | |
| Polar Surface Area (PSA) | 42.01 |
| Rotatable Bond (RotB) | 12 |
| Matching Veber Rules | 1 |
| Bioactivity |
| In vitro: Efficacy |
| Quantitative Results |
| pX | Parameter | Value (qual) | Value (quant) | Unit |
| 6.96 | IC50 | 110 | nM | |
| 6.35 | IC50 | 0.45 | µM | |
| 6.03 | EC50 | 0.94 | µM | |
| 5.6 | EC50 | 2.5 | µM | |
| 4.72 | IC50 | 19 | μM | |
| 4.15 | IC50 | 70 | μM | |
| 3.81 | ID50 | = | 75 | μg/ml |
| 1 | IC50 | > | 50 | μM |
| 1 | nH (Hill coefficient) | 1.1 | ||
| Emax | 6.7 | |||
| viable cell percentage(Stationary phase bacteria) | 44 | % | ||
| Protein binding (%) | 52 | % | ||
| tested | Not Published | |||
| viable cell percentage(at 72hpi) | >= | 90 | % |
| Quantitative Results | ||
| 1 of 5 | Effect | antiviral agent |
| 2 of 5 | Effect | Cytotoxic |
| Biological material | bovine fibroblast | |
| Assay Description | Bioassay : for morphological studies cell seeded into 35-mmplastic culture dishes; for ultrastructural exam.cells grown on the plastic surface used; for radiochemical and biochemical experiments cells seeded into plastic flasks of 25ml and 75 ml, respectively fibroblasts obtained from explants of bovine corneae; cells cultivated in Eagle’s minimal essential medium (MEM) suppl.with 10 percent fetal calf serum, non-essential amino acids, penicillin and streptomicin at 37 degC; pH 7.1-7.2 | |
| Results | induces lisosomal GAG contents. | |
| 3 of 5 | Results | Surviving curves of T2 phage with the compound at 37 deg C. |
| 4 of 5 | Results | inhibition of cAMP-phosphodiesterase in cell homogenates of peritoneal macrophages and L 1210 aszites: 50percent inhibition at concentrations 440.2 and 792.4 μmol/l, respectively |
| 5 of 5 | Results | effect of title compound pretreatment on body weight loss and antipyrine disposition in vivo (rat); pharmacokinetic parameters |
| Toxicity/Safety Pharmacology |
| Quantitative Results |
| pX | Parameter | Value (qual) | Effect |
| 1 | body weight loss | Not active | Toxic |
| body weight gain(Survivors) | Active | toxic substance |
| Use Pattern |
| Tilorone dihydrochloride CAS#: 27591-69-1 as Pharmaceuticals |
| Tilorone dihydrochloride CAS#: 27591-69-1 treating a Zika viral infection |
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