[[2-(6-amino-9H-purine-9-yl)ethoxy]methyl]phosphonic acid diethyl ester
Adefovir
Conditions | Yield |
---|---|
With trimethylsilyl bromide | 95% |
Stage #1: [[2-(6-amino-9H-purine-9-yl)ethoxy]methyl]phosphonic acid diethyl ester With trimethylsilyl bromide In acetonitrile at 20℃; for 3h; Large scale; Stage #2: With sodium hydroxide In water for 2h; Reflux; Large scale; | 86.3% |
With hydrogen bromide In water at 90℃; for 5h; Temperature; Time; | 86% |
[2-(6-Amino-purin-9-yl)-ethoxymethyl]-phosphonic acid diisopropyl ester
Adefovir
Conditions | Yield |
---|---|
With hydrogenchloride In water at 140℃; for 0.166667h; Microwave irradiation; Sealed tube; | 95% |
Multi-step reaction with 2 steps 1: acetonitrile 2: aq. NH3 View Scheme |
Methyl Ester of 9-(2-Phosphonylmethoxyethyl)adenine
Adefovir
Conditions | Yield |
---|---|
With trimethylsilyl iodide; triethylamine carbonate 1) DMF, R.T., 16 h 2) 80 deg C; Yield given. Multistep reaction; |
diethyl (p-toluenesulfonyloxymethane)phosphonate
9-(2-hydroxyethyl)adenine
Adefovir
Conditions | Yield |
---|---|
With trimethylsilyl bromide; sodium t-butanolate 1.) DMF; Yield given. Multistep reaction; |
Adefovir
Conditions | Yield |
---|---|
With ammonium hydroxide Yield given; | |
With water | 33.0 g |
[2-(5-Amino-6-chloro-pyrimidin-4-ylamino)-ethoxymethyl]-phosphonic acid diethyl ester
Adefovir
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 92 percent / 3 h / 120 °C 2: 87 percent / NH3 liquid / tetrahydrofuran; dimethylsulfoxide / 24 h / 25 °C 3: 95 percent / TMSBr View Scheme |
O,O-diethyl((2-(6-chloro-9H-purin-9-yl)ethoxy)methyl)phosphonate
Adefovir
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 87 percent / NH3 liquid / tetrahydrofuran; dimethylsulfoxide / 24 h / 25 °C 2: 95 percent / TMSBr View Scheme |
9-(2-Hydroxyethyl)-N6-benzoyladenine
Adefovir
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 1) NaH 2) 0.5 mol l-1 NaOH / 1)DMF, R.T., 48 h, 2) 50 deg C, 6 h 2: 1) iodotrimethylsilane 2) 2 mol l-1 triethylammonium hydrogen carbonate / 1) DMF, R.T., 16 h 2) 80 deg C View Scheme |
9-(2-hydroxyethyl)adenine
Adefovir
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 81 percent / chlorotrimethylsilane / pyridine 2: 1) NaH 2) 0.5 mol l-1 NaOH / 1)DMF, R.T., 48 h, 2) 50 deg C, 6 h 3: 1) iodotrimethylsilane 2) 2 mol l-1 triethylammonium hydrogen carbonate / 1) DMF, R.T., 16 h 2) 80 deg C View Scheme | |
Multi-step reaction with 2 steps 1: 1) NaH, 2) 0.5 mol l-1 NaOH / 1) DMF, R.T., 48 h, 2) 50 deg C, 6 h 2: 1) iodotrimethylsilane 2) 2 mol l-1 triethylammonium hydrogen carbonate / 1) DMF, R.T., 16 h 2) 80 deg C View Scheme | |
Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 5 °C / Large scale 1.2: 5 h / 5 °C / Large scale 2.1: trimethylsilyl bromide / acetonitrile / 3 h / 20 °C / Large scale 2.2: 2 h / Reflux; Large scale View Scheme | |
Multi-step reaction with 2 steps 1: magnesium 2-methylpropan-2-olate / N,N-dimethyl-formamide / 12 h / 80 °C 2: chloro-trimethyl-silane / chlorobenzene / 10 h / 120 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: magnesium 2-methylpropan-2-olate / N,N-dimethyl-formamide / 1 h / 78 - 82 °C 1.2: 78 - 82 °C 2.1: trimethylsilyl bromide / 80 - 85 °C View Scheme |
Conditions | Yield |
---|---|
In dichloromethane; water; acetone |
Adefovir
Conditions | Yield |
---|---|
for 24h; Conversion of starting material; Complete medium (extra-cellular medium mimick); | |
With CEM-SS culture medium at 37℃; pH=7.4; aq. buffer; |
{[2-(6-amino-9H-purin-9-yl)ethoxy]methyl}phosphinic acid
Adefovir
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: pyridine; N,O-bis-(trimethylsilyl)-acetamide / 1 h / 20 °C / Inert atmosphere 1.2: 0.5 h / Inert atmosphere 1.3: Dowex 50WX2 (Na+ form) 2.1: CEM-SS culture medium / 37 °C / pH 7.4 / aq. buffer View Scheme |
Adefovir
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 25 - 85 °C 1.2: 20 h 2.1: water; hydrogen bromide / 4 h / 90 - 95 °C 2.2: 25 - 30 °C / pH 2.8 View Scheme | |
Multi-step reaction with 3 steps 1: triethylamine / acetonitrile / 14 h / 125 °C / Inert atmosphere 2: magnesium 2-methylpropan-2-olate / N,N-dimethyl-formamide / 12 h / 80 °C 3: chloro-trimethyl-silane / chlorobenzene / 10 h / 120 °C View Scheme |
Conditions | Yield |
---|---|
With ethylenediaminetetraacetic acid; DL-dithiothreitol; water; magnesium chloride In aq. buffer at 37℃; for 18h; pH=7.5; Enzymatic reaction; |
adefovir dipivoxyl
Adefovir
Conditions | Yield |
---|---|
With ethylenediaminetetraacetic acid; DL-dithiothreitol; water; magnesium chloride In aq. buffer at 37℃; for 1h; pH=7.5; Enzymatic reaction; |
Adefovir
Conditions | Yield |
---|---|
With ethylenediaminetetraacetic acid; DL-dithiothreitol; water; magnesium chloride In aq. buffer at 37℃; for 18h; pH=7.5; Enzymatic reaction; |
C18H30N7O6P
Adefovir
Conditions | Yield |
---|---|
With ethylenediaminetetraacetic acid; DL-dithiothreitol; water; magnesium chloride In aq. buffer at 37℃; for 18h; pH=7.5; Enzymatic reaction; |
6-Chloro-9-(β-hydroxyethylamino)purine
Adefovir
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: sodium hydride / tetrahydrofuran / -20 - 0 °C / Inert atmosphere 1.2: 48 h / 50 °C 2.1: trimethylhalosilane / acetonitrile / 20 °C / Inert atmosphere; Cooling with ice View Scheme |
6-chloro-9-(ethoxycarbonylmethyl)-9H-purine
Adefovir
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: methanol; sodium tetrahydroborate / 0 °C 2.1: sodium hydride / tetrahydrofuran / -20 - 0 °C / Inert atmosphere 2.2: 48 h / 50 °C 3.1: trimethylhalosilane / acetonitrile / 20 °C / Inert atmosphere; Cooling with ice View Scheme |
6-chloropurine
Adefovir
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: scandium tris(trifluoromethanesulfonate) / acetonitrile / 0.17 h / 20 °C 2.1: methanol; sodium tetrahydroborate / 0 °C 3.1: sodium hydride / tetrahydrofuran / -20 - 0 °C / Inert atmosphere 3.2: 48 h / 50 °C 4.1: trimethylhalosilane / acetonitrile / 20 °C / Inert atmosphere; Cooling with ice View Scheme |
9-(2-hydroxyethyl)adenine
Adefovir
Conditions | Yield |
---|---|
Stage #1: 9-(2-hydroxyethyl)adenine With magnesium 2-methylpropan-2-olate In N,N-dimethyl acetamide at 90℃; for 0.5h; Schlenk technique; Inert atmosphere; Stage #2: (di-tert-butoxyphosphoryl)methyl methanesulfonate In N,N-dimethyl acetamide at 90℃; for 22h; Schlenk technique; Inert atmosphere; Stage #3: With hydrogenchloride In water at 60℃; Schlenk technique; Inert atmosphere; |
Conditions | Yield |
---|---|
With dicyclohexyl-carbodiimide In water; tert-butyl alcohol for 11h; Heating; | 96% |
Adefovir
9-(2-Phosphonylmethoxyethyl)hypoxanthine
Conditions | Yield |
---|---|
With isopentyl nitrite In acetic acid for 72h; Ambient temperature; | 93% |
Conditions | Yield |
---|---|
With water at 90℃; for 3h; | 90% |
Conditions | Yield |
---|---|
With oxalyl dichloride In dichloromethane for 4.5h; Heating / reflux; | 89% |
With oxalyl dichloride In dichloromethane for 4.5h; Heating / reflux; |
Adefovir
(Z)-4-(2-chloroethylidenyl)-2,3-dimethoxy-Δα,β-butenolide
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 25℃; for 1h; | 88% |
1,1,1-trichloroethanol
Adefovir
Conditions | Yield |
---|---|
With thionyl chloride In N,N-dimethyl-formamide for 16h; Ambient temperature; | 86% |
methanol
Adefovir
Methyl Ester of 9-(2-Phosphonylmethoxyethyl)adenine
Conditions | Yield |
---|---|
With thionyl chloride In N,N-dimethyl-formamide for 16h; Ambient temperature; | 85% |
Conditions | Yield |
---|---|
With hydrogenchloride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In water at 20℃; | 85% |
Conditions | Yield |
---|---|
With triethylamine In dichloromethane; N,N-dimethyl-formamide at 20℃; for 24h; | 79.36% |
2-chloroethanal
Adefovir
9-(2-phosphonylmethoxyethyl)-1,N6-ethenoadenine
Conditions | Yield |
---|---|
In water at 40℃; for 24h; pH 4.5; | 78.1% |
Conditions | Yield |
---|---|
With triethylamine In 1-methyl-pyrrolidin-2-one at 50 - 55℃; Solvent; Reagent/catalyst; Temperature; Inert atmosphere; Large scale; | 78.1% |
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 25℃; for 24h; | 75% |
With tetrabutylammomium bromide; triethylamine In 1-methyl-pyrrolidin-2-one at 65 - 75℃; for 2h; Temperature; Reagent/catalyst; Solvent; | 57.5% |
Conditions | Yield |
---|---|
In ethanol; water at 90℃; for 3h; | 75% |
2,2,2-trifluoroethanol
Adefovir
Conditions | Yield |
---|---|
With thionyl chloride In N,N-dimethyl-formamide for 16h; Ambient temperature; | 74% |
Conditions | Yield |
---|---|
With thionyl chloride In N,N-dimethyl-formamide for 16h; Product distribution; Ambient temperature; various hydroxylic components under different reaction conditions; | 73% |
With thionyl chloride In N,N-dimethyl-formamide for 16h; Ambient temperature; | 73% |
Conditions | Yield |
---|---|
With water at 90℃; for 2h; | 70% |
2-(morpholin-4-yl)ethanol
Adefovir
Conditions | Yield |
---|---|
With thionyl chloride In N,N-dimethyl-formamide for 16h; Ambient temperature; | 68% |
2,2,2-tribromoethanol
Adefovir
Conditions | Yield |
---|---|
With thionyl chloride In N,N-dimethyl-formamide for 48h; Ambient temperature; | 64% |
N,N-dimethylformamide dibenzyl acetal
Adefovir
Conditions | Yield |
---|---|
at 60℃; for 48h; | 60% |
Adefovir
ethylene glycol
Conditions | Yield |
---|---|
With thionyl chloride In N,N-dimethyl-formamide for 16h; Ambient temperature; | 57% |
Conditions | Yield |
---|---|
With thionyl chloride In N,N-dimethyl-formamide for 16h; Ambient temperature; | 56% |
Adefovir
3-Hydroxypropionitrile
Conditions | Yield |
---|---|
With thionyl chloride In N,N-dimethyl-formamide for 4h; Ambient temperature; | 51% |
Adefovir
glycine ethyl ester hydrochloride
9-(bis(N,N'-(methoxycarbonylmethyl)phosphonamido)methoxyethyl)adenine
Conditions | Yield |
---|---|
With 2,2'-dipyridyldisulphide; triethylamine; triphenylphosphine In pyridine at 90℃; for 24h; Mukaiyama reaction; Inert atmosphere; | 51% |
Adefovir
9-[2-(phosphonomethoxy)ethyl]adenine bis(3,6,9,12,15,18-hexaoxaeicosyl) ester
Conditions | Yield |
---|---|
Stage #1: Adefovir With tetra(n-butyl)ammonium hydroxide In methanol Stage #2: 3,6,9,12,15,1 8-hexaoxaicosyl p-toluensulfonate In N,N-dimethyl-formamide at 100℃; | 50% |
Adefovir
Conditions | Yield |
---|---|
With aq. HNO3 In water aq. soln. of org. compd. slowly added to soln. of complex (pH= 1.3 adjusted with 1 M HNO3) during 3 h, stirred for 24 h at 35°C; volatiles evapd. at room temp. in N2 stream, treated twice with MeOH (12 h, ambient temp.), foltered, elem. anal.; | 49% |
(S)-(-)-1-(3'-Chlorophenyl)-1,3-Propanediol
Adefovir
Conditions | Yield |
---|---|
With pyridine; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 100℃; | A 48% B n/a |
With pyridine; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 100℃; |
Adefovir
Conditions | Yield |
---|---|
With thionyl chloride In N,N-dimethyl-formamide for 16h; Ambient temperature; | 47% |
Conditions | Yield |
---|---|
With thionyl chloride In N,N-dimethyl-formamide for 16h; Ambient temperature; | 46% |
Molecular Structure of 9-(2-Phosphonylmethoxyethyl)adenine (CAS NO.106941-25-7):
Molecular Formula: C8H12N5O4P
Molecular Weight: 273.1857
IUPAC Name: 2-(6-Aminopurin-9-yl)ethoxymethylphosphonic acid
Synonyms of 9-(2-Phosphonylmethoxyethyl)adenine (CAS NO.106941-25-7): Adefovir [USAN:INN] ; ((2-(6-Amino-9H-purin-9-yl)ethoxy)methyl)phosphonic acid ; 9-(2-(Phosphonomethoxy)ethyl)adenine ; Adefovir ; BRN 3561094 ; DRG-0156 ; GS 0393 ; GS 393 ; GS-0393 ; N-(2-Phophonomethoxyethyl-2,6-diaminopurine) ; N-(2-Phosphonylmethoxyethyl)adenine ; PMEA ; Phosphonic acid, ((2-(6-amino-9H-purin-9-yl)ethoxy)methyl)- ; UNII-6GQP90I798
CAS NO: 106941-25-7
Classification Code: Anti-Infective Agents ; Anti-Retroviral Agents ; Antiviral ; Antiviral agents ; Enzyme Inhibitors ; Mutation data ; Nucleic Acid Synthesis Inhibitors ; Reverse Transcriptase Inhibitors
Melting point: >260°C
Index of Refraction: 1.768
Molar Refractivity: 60.14 cm3
Molar Volume: 144.9 cm3
Surface Tension: 103.8 dyne/cm
Density: 1.88 g/cm3
Flash Point: 336.3 °C
Enthalpy of Vaporization: 98.29 kJ/mol
Boiling Point: 632.5 °C at 760 mmHg
Vapour Pressure: 7.24E-17 mmHg at 25°C
9-(2-Phosphonylmethoxyethyl)adenine (CAS NO.106941-25-7) can be used for antiviral.
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD | intravenous | > 1gm/kg (1000mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | Antimicrobial Agents and Chemotherapy. Vol. 40, Pg. 1072, 1996. |
mouse | LDLo | intraperitoneal | 1600mg/kg (1600mg/kg) | Antimicrobial Agents and Chemotherapy. Vol. 40, Pg. 1072, 1996. |
Mutation data reported. When heated to decomposition it emits toxic vapors of NOx and POx.
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