N2-acetyl-9-(1,3-dihydroxy-2-propoxymethyl)guanine
ganciclovir
Conditions | Yield |
---|---|
With ammonium hydroxide In methanol at 20℃; for 17h; | 94% |
With ammonium hydroxide In methanol at 25℃; for 16h; Yield given; |
9-(1,3-diacetoxy-2-propoxymethyl)-N2-acetylguanine
ganciclovir
Conditions | Yield |
---|---|
With ammonium hydroxide for 72h; Ambient temperature; | 91% |
With acetic acid In water; methylamine | 87% |
With potassium hydroxide at 70℃; for 0.5h; Reagent/catalyst; Microwave irradiation; | 82.8% |
With methanol; potassium hydroxide at 20℃; for 12h; | 78% |
With acetic acid In methylamine |
9-<<2-(benzyloxy)-1-<(benzyloxy)methyl>ethoxy>methyl>guanine
ganciclovir
Conditions | Yield |
---|---|
palladium dichloride In ethanol; cyclohexene for 5h; Heating; | 90% |
With palladium; cyclohexene In ethanol | 87.7% |
With cyclohexene; palladium In ethanol for 24h; Heating; | 87.7% |
With cyclohexene; palladium In ethanol |
9-<<2-benzyloxy-1-(benzyloxymethyl)ethoxy>methyl>guanine
ganciclovir
Conditions | Yield |
---|---|
With ethanol; palladium In cyclohexene for 18h; Heating; | 84% |
N2-acetyl-9-((1,3-pivaloyloxy-2-propoxy)methyl)guanine
ganciclovir
Conditions | Yield |
---|---|
With sodium methylate In methanol for 40h; Heating; | 72% |
1-<(1,3-dihydroxy-2-propoxy)methyl>-5-<(thiocarbamoyl)amino>-1H-imidazole-4-carboxamide
ganciclovir
Conditions | Yield |
---|---|
With sodium hydroxide; copper(II) sulfate for 1h; Heating; | 61% |
2-(2-amino-1,6-dihydro-6-oxopurin-9-yl)methoxy-1,3-bis-1'-propyl-(2'S)-azido-3'-methylbutanoate
A
2-[(2-amino-1,6-dihydro-6-oxopurin-9-yl)methyloxy]-3-hydroxypropyl 2'-(S)-azido-3'-methylbutanoate
B
ganciclovir
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In methanol at 20℃; for 14h; | A 34.5% B 20 %Chromat. |
C23H21N5O6
ganciclovir
Conditions | Yield |
---|---|
With ammonia In methanol Yield given; |
9-<<2-hydroxy-1-(hydroxymethyl)ethoxy>methyl>-2,6-diamino-purine
ganciclovir
Conditions | Yield |
---|---|
at 25℃; for 18h; adenosine deaminase, pH = 7.5; |
9-<(1-acetoxy-2-hydroxymethyl)ethoxymethyl>guanine
A
ganciclovir
B
acetic acid
Conditions | Yield |
---|---|
With New Zealand albino male rabbit cornea homogenate In phosphate buffer at 37℃; for 24h; Kinetics; Further Variations:; Reagents; |
Conditions | Yield |
---|---|
With New Zealand albino male rabbit cornea homogenate In phosphate buffer at 37℃; for 24h; Kinetics; Further Variations:; Reagents; |
Conditions | Yield |
---|---|
With New Zealand albino male rabbit cornea homogenate In phosphate buffer at 37℃; for 24h; Kinetics; Further Variations:; Reagents; |
Conditions | Yield |
---|---|
With New Zealand albino male rabbit cornea homogenate In phosphate buffer at 37℃; for 24h; Kinetics; Further Variations:; Reagents; |
Conditions | Yield |
---|---|
With New Zealand albino male rabbit cornea homogenate In phosphate buffer at 37℃; for 24h; Kinetics; Further Variations:; Reagents; |
Conditions | Yield |
---|---|
With New Zealand albino male rabbit cornea homogenate In phosphate buffer at 37℃; for 24h; Kinetics; Further Variations:; Reagents; |
Conditions | Yield |
---|---|
With New Zealand albino male rabbit cornea homogenate In phosphate buffer at 37℃; for 24h; Kinetics; Further Variations:; Reagents; |
Conditions | Yield |
---|---|
With New Zealand albino male rabbit cornea homogenate In phosphate buffer at 37℃; for 24h; Kinetics; Further Variations:; Reagents; |
2-amino-1,9-dihydro-6H-purin-6-one
ganciclovir
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: (NH4)2SO4 2: Bu4NF / tetrahydrofuran 3: cyclohexene / Pd / ethanol View Scheme | |
Multi-step reaction with 3 steps 1: ammonium sulfate / 96 h / Heating 2: 17.8 percent / tetrabutylammonium fluoride / tetrahydrofuran / 22 h / Heating 3: 87.7 percent / cyclohexene / palladium black / ethanol / 24 h / Heating View Scheme | |
Multi-step reaction with 3 steps 1: (NH4)2SO4 2: Bu4NF / tetrahydrofuran 3: 87.7 percent / Pd black; cyclohexene / ethanol View Scheme |
2,6,9-tris(trimethylsilyl)guanine
ganciclovir
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: Bu4NF / tetrahydrofuran 2: cyclohexene / Pd / ethanol View Scheme | |
Multi-step reaction with 2 steps 1: 17.8 percent / tetrabutylammonium fluoride / tetrahydrofuran / 22 h / Heating 2: 87.7 percent / cyclohexene / palladium black / ethanol / 24 h / Heating View Scheme | |
Multi-step reaction with 2 steps 1: Bu4NF / tetrahydrofuran 2: 87.7 percent / Pd black; cyclohexene / ethanol View Scheme |
N2-acetyl-9-<<1,3-bis(benzyloxy)-2-propoxy>methyl>guanine
ganciclovir
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 90 percent / EtOH / Pd(OH)2/C / cyclohexane / 40 h / Heating 2: 94 percent / aq. ammonium hydroxide / methanol / 17 h / 20 °C View Scheme | |
Multi-step reaction with 2 steps 1: 20percent Pd(OH)2/C / cyclohexene; ethanol / 32 h / Heating 2: 56percent NH4OH / methanol / 16 h / 25 °C View Scheme | |
Multi-step reaction with 2 steps 1: 99 percent / conc. ammonium hydroxide, pyridine / 15 h / 55 °C 2: 84 percent / ethanol / palladium black / cyclohexene / 18 h / Heating View Scheme |
2,9-diacetylguanine
ganciclovir
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 31 percent / p-toluenesulfonic acid / tetrahydrothiophene 1,1-dioxide / 85 h / 95 °C 2: 90 percent / EtOH / Pd(OH)2/C / cyclohexane / 40 h / Heating 3: 94 percent / aq. ammonium hydroxide / methanol / 17 h / 20 °C View Scheme |
7-(1,3-diacetoxy-2-propoxymethyl)-N2-acetylguanine
ganciclovir
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 50 percent / 0.17 h / 230 °C 2: 91 percent / NH4OH / 72 h / Ambient temperature View Scheme |
N-(6-oxo-6,9-dihydro-1H-purin-2-yl)acetamide
ganciclovir
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 1.) HMDS, ammonium sulfate; 2.) TBAI; 3.)methanol, water 2: 99 percent / conc. ammonium hydroxide, pyridine / 15 h / 55 °C 3: 84 percent / ethanol / palladium black / cyclohexene / 18 h / Heating View Scheme | |
Multi-step reaction with 3 steps 1: potassium carbonate / N,N-dimethyl-formamide / 8 h / 20 °C 2: palladium diacetate; bis(tertbutylcarbonyloxy)iodobenzene / toluene / 24 h / 120 °C 3: methanol; potassium hydroxide / 12 h / 20 °C View Scheme |
2,6-bisacetamidopurine
ganciclovir
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 5.4 g / triethylamine / dimethylformamide / 1.) r.t. 60 h; 2.) 40 deg C, 1 h 2: 85 percent / Na / methanol / 1.) reflux, 2 h; 2.) r.t. 12 h 3: 80 percent / palladium oxide, cyclohexene / ethanol / 3 h / Heating 4: 18 h / 25 °C / adenosine deaminase, pH = 7.5 View Scheme |
9-(2-Benzyloxy-1-benzyloxymethyl-ethoxymethyl)-9H-purine-2,6-diamine
ganciclovir
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 80 percent / palladium oxide, cyclohexene / ethanol / 3 h / Heating 2: 18 h / 25 °C / adenosine deaminase, pH = 7.5 View Scheme |
N-[2-Acetylamino-9-(2-benzyloxy-1-benzyloxymethyl-ethoxymethyl)-9H-purin-6-yl]-acetamide
ganciclovir
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 85 percent / Na / methanol / 1.) reflux, 2 h; 2.) r.t. 12 h 2: 80 percent / palladium oxide, cyclohexene / ethanol / 3 h / Heating 3: 18 h / 25 °C / adenosine deaminase, pH = 7.5 View Scheme |
9-<<2-benzyloxy-1-(benzyloxymethyl)ethoxy>-methyl>-6-chloroguanine
ganciclovir
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 70 percent / sodium, mercaptoethanol, water / methanol / 2.5 h / Heating 2: 84 percent / ethanol / palladium black / cyclohexene / 18 h / Heating View Scheme |
2-Amino-6-chloropurin
ganciclovir
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 1.) 1,1,1,3,3,3-hexamethyldisilazane, ammonium sulfate; 2.) mercuric cyanide / 1.) 2 h, reflux; 2.) benzene, 3 h, reflux 2: 70 percent / sodium, mercaptoethanol, water / methanol / 2.5 h / Heating 3: 84 percent / ethanol / palladium black / cyclohexene / 18 h / Heating View Scheme |
5-amino-1-<(1,3-dihydroxy-2-propoxy)methyl>-1H-imidazole-4-carboxamide
ganciclovir
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 2) K2CO3 / 1) acetone, reflux, 1 h, 2) methanol, reflux, 4 h 2: 61 percent / 3N aq. NaOH, copper(II) sulfate / 1 h / Heating View Scheme |
ganciclovir
2-Methylpropionic anhydride
Conditions | Yield |
---|---|
With pyridine; dmap for 1h; Acylation; Heating; | 99% |
ganciclovir
1-hexadecylcarboxylic acid
Conditions | Yield |
---|---|
With dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 50℃; for 50h; | 97% |
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 50℃; for 5h; Inert atmosphere; | 96.8% |
ganciclovir
tert-butyldimethylsilyl chloride
9-<(1,3-bis(tert-butyldimethylsilyloxy)-2-propoxy)methyl>guanine
Conditions | Yield |
---|---|
With 1H-imidazole In N,N-dimethyl-formamide for 1h; Ambient temperature; | 95% |
ganciclovir
Conditions | Yield |
---|---|
With phosphorus pentachloride In tetrahydrofuran at 0 - 10℃; for 1h; | 92.7% |
ganciclovir
acetic anhydride
9-(1,3-diacetoxy-2-propoxymethyl)guanine
Conditions | Yield |
---|---|
With dmap Ambient temperature; | 91% |
With dmap In N,N-dimethyl-formamide at 23℃; Acetylation; | 90% |
ganciclovir
tert-butylchlorodiphenylsilane
2-amino-9-[2-(tert-butyl-diphenyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxymethyl)-ethoxymethyl]-1,9-dihydro-purin-6-one
Conditions | Yield |
---|---|
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 24h; Substitution; silylation; | 91% |
trimethyl orthovalerate
ganciclovir
Conditions | Yield |
---|---|
Stage #1: trimethyl orthovalerate; ganciclovir With trifluoroacetic acid In N,N-dimethyl-formamide at 23℃; for 2h; Substitution; Stage #2: With water In N,N-dimethyl-formamide at 23℃; Hydrolysis; | A 90% B 5% |
ganciclovir
azidovaline
2-(2-amino-1,6-dihydro-6-oxopurin-9-yl)methoxy-1,3-bis-1'-propyl-(2'S)-azido-3'-methylbutanoate
Conditions | Yield |
---|---|
Stage #1: ganciclovir With benzotriazol-1-ol; triethylamine In dimethyl sulfoxide at 25 - 30℃; for 0.166667h; Stage #2: azidovaline In dimethyl sulfoxide at 25 - 30℃; Stage #3: With dicyclohexyl-carbodiimide In dimethyl sulfoxide at 25 - 30℃; for 2h; | 88.8% |
Stage #1: ganciclovir With triethanolamine; benzotriazol-1-ol In dimethyl sulfoxide at 25 - 30℃; Stage #2: azidovaline With dicyclohexyl-carbodiimide In dimethyl sulfoxide at 20 - 30℃; |
Conditions | Yield |
---|---|
With dmap In N,N-dimethyl-formamide at 23℃; Esterification; | 88% |
With dmap Ambient temperature; | 52% |
ganciclovir
1,1'-carbonyldiimidazole
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 50℃; for 18h; | 87% |
Conditions | Yield |
---|---|
Stage #1: trimethoxypropane; ganciclovir With trifluoroacetic acid In N,N-dimethyl-formamide at 23℃; for 2h; Substitution; Stage #2: With water In N,N-dimethyl-formamide at 23℃; Hydrolysis; | A 87% B 6% |
Conditions | Yield |
---|---|
With dmap Ambient temperature; | 86% |
With dmap In N,N-dimethyl-formamide at 23℃; Esterification; | 80% |
ganciclovir
4-isobutyryloxyphenacyl bromide
isobutyric acid 4-[3-(2-hydroxy-1-hydroxymethyl-ethoxymethyl)-8-oxo-5,8-dihydro-3H-1,3,4,5,7a-pentaaza-s-indacen-6-yl]-phenyl ester
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide | 86% |
Stage #1: ganciclovir With sodium hydride In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: 4-isobutyryloxyphenacyl bromide In N,N-dimethyl-formamide at 20℃; for 4h; Further stages.; | 55% |
With sodium hydride In N,N-dimethyl-formamide at 20℃; for 4h; |
ganciclovir
2,2-dimethylpropanoic anhydride
Conditions | Yield |
---|---|
With dmap In N,N-dimethyl-formamide for 48h; Ambient temperature; | 84% |
ganciclovir
N,N-dimethyl-formamide dimethyl acetal
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 20℃; for 29h; | 84% |
Conditions | Yield |
---|---|
Stage #1: 1,1,1-trimethoxybutane; ganciclovir With trifluoroacetic acid In N,N-dimethyl-formamide at 23℃; for 2h; Substitution; Stage #2: With water In N,N-dimethyl-formamide at 23℃; Hydrolysis; | A 83% B 15% |
ganciclovir
N-(Benzyloxycarbonyl)glycine
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 20℃; for 48h; Acylation; | 81% |
Conditions | Yield |
---|---|
With dmap In N,N-dimethyl-formamide at 23℃; Esterification; | 80% |
ganciclovir
acetic anhydride
9-(1,3-diacetoxy-2-propoxymethyl)-N2-acetylguanine
Conditions | Yield |
---|---|
With pyridine for 6h; Reflux; | 80% |
undecylenic acid
ganciclovir
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 23℃; for 48h; Esterification; | 78% |
benzaldehyde dimethyl acetal
ganciclovir
Conditions | Yield |
---|---|
Stage #1: benzaldehyde dimethyl acetal; ganciclovir With toluene-4-sulfonic acid In dimethyl sulfoxide at 25 - 80℃; Stage #2: With triethylamine In water; dimethyl sulfoxide; ethyl acetate at 25 - 35℃; | 78% |
Isovaleric anhydride
ganciclovir
Conditions | Yield |
---|---|
Stage #1: ganciclovir With pyridine; chloro-trimethyl-silane at 20℃; for 0.25h; Stage #2: Isovaleric anhydride at 20℃; for 3h; Stage #3: With ammonia In water | 76.8% |
N-Acetylimidazole
ganciclovir
9-<(1-acetoxy-2-hydroxymethyl)ethoxymethyl>guanine
Conditions | Yield |
---|---|
Stage #1: ganciclovir With Trimethyl borate In toluene for 5h; Reflux; Large scale; Stage #2: N-Acetylimidazole With triethylamine at 20℃; for 6h; Large scale; Stage #3: In methanol at 0 - 20℃; for 2h; Reagent/catalyst; Solvent; Large scale; | 75.7% |
Stage #1: ganciclovir With Trimethyl borate In toluene for 5h; Reflux; Stage #2: N-Acetylimidazole With triethylamine In toluene at 20℃; for 6h; Stage #3: With methanol In toluene at 0 - 20℃; for 2h; Reagent/catalyst; Solvent; | 75.7% |
Stage #1: ganciclovir With Trimethyl borate In toluene for 5h; Reflux; Stage #2: N-Acetylimidazole With triethylamine In toluene at 20℃; for 6h; Stage #3: With methanol In toluene at 0 - 20℃; for 2h; Reagent/catalyst; Solvent; | 75.7% |
Stage #1: ganciclovir With Trimethyl borate In toluene for 5h; Reflux; Stage #2: N-Acetylimidazole With triethylamine In toluene at 20℃; for 6h; Reagent/catalyst; Solvent; | 75.7% |
vinyl acetate
ganciclovir
9-<(1-acetoxy-2-hydroxymethyl)ethoxymethyl>guanine
Conditions | Yield |
---|---|
Stage #1: ganciclovir With triethyl borate In 2-methyltetrahydrofuran for 3h; Reflux; Large scale; Stage #2: vinyl acetate With triethylamine at 20℃; for 6h; Large scale; Stage #3: In ethanol at 0 - 20℃; for 3h; Reagent/catalyst; Solvent; Large scale; | 75.2% |
Stage #1: ganciclovir With triethyl borate In 2-methyltetrahydrofuran for 3h; Reflux; Stage #2: vinyl acetate With triethylamine In 2-methyltetrahydrofuran at 20℃; for 6h; Stage #3: With ethanol In 2-methyltetrahydrofuran at 0 - 20℃; for 2h; Reagent/catalyst; Solvent; | 75.2% |
Stage #1: ganciclovir With triethyl borate In 2-methyltetrahydrofuran for 3h; Reflux; Stage #2: vinyl acetate With triethylamine In tetrahydrofuran at 20℃; for 6h; Stage #3: With ethanol In tetrahydrofuran at 0 - 20℃; for 3h; Reagent/catalyst; Solvent; | 75.2% |
Stage #1: ganciclovir With triethyl borate In 2-methyltetrahydrofuran for 3h; Reflux; Stage #2: vinyl acetate With triethylamine In 2-methyltetrahydrofuran at 20℃; for 6h; Reagent/catalyst; Solvent; | 75.2% |
1. Introduction of Ganciclovir
Ganciclovir, with the IUPAC Name of 2-Amino-9-(1,3-dihydroxypropan-2-yloxymethyl)-3H-purin-6-one, is one kind of white powder. This chemical has the Classification Code which include Anti-Infective Agents; Antiviral; Antiviral agents; Drug / Therapeutic Agent; Mutation data. Besides, it belongs to the Product Categories which include Bases & Related Reagents; Intermediates & Fine Chemicals; Nucleotides; Pharmaceuticals; API's; Antiviral.
2. Properties of Ganciclovir
Ganciclovir has the following properties: (1)Index of Refraction: 1.76; (2)Molar Refractivity: 57.9 cm3; (3)Molar Volume: 140.5 cm3; (4)Polarizability: 22.95×10-24 cm3; (5)Surface Tension: 86.6 dyne/cm; (6)Density: 1.81 g/cm3; (7)Flash Point: 362 °C; (8)Enthalpy of Vaporization: 104.13 kJ/mol; (9)Boiling Point: 675 °C at 760 mmHg; (10)Melting Point: 250 °C; (11)storage temperature: 2-8 °C; (12)solubility: 0.1 M HCl: 10 mg/mL; (13)Vapour Pressure: 3.82E-19 mmHg at 25 °C.
3. Structure Descriptors of Ganciclovir
You could convert the following datas into the molecular structure:
(1).Canonical SMILES: c12c(ncn1COC(CO)CO)c([nH]c(n2)N)=O
(2).InChI: InChI=1/C9H13N5O4/c10-9-12-7-6(8(17)13-9)11-3-14(7)4-18-5(1-15)2-16/h3,5,15-16H,1-2,4H2,(H3,10,12,13,17)
4. Toxicity of Ganciclovir
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
dog | LD50 | intravenous | > 150mg/kg (150mg/kg) | Drugs in Japan Vol. -, Pg. 291, 1990. | |
dog | LD50 | oral | > 1gm/kg (1000mg/kg) | Drugs in Japan Vol. -, Pg. 291, 1990. | |
mouse | LD50 | intraperitoneal | 1gm/kg (1000mg/kg) | Journal of Medicinal Chemistry. Vol. 26, Pg. 759, 1983. | |
mouse | LD50 | intravenous | 900mg/kg (900mg/kg) | Drugs in Japan Vol. -, Pg. 291, 1990. | |
mouse | LD50 | oral | > 2gm/kg (2000mg/kg) | Drugs in Japan Vol. -, Pg. 291, 1990. |
5. Safety Information of Ganciclovir
Common adverse drug reactions >=1% of patients) include: neutropenia, granulocytopenia, thrombocytopenia, fever, nausea, vomiting, dyspepsia, diarrhoea, abdominal pain, flatulence, anorexia, raised liver enzymes, headache, confusion, hallucination, anaemia, pain and phlebitis at injection site (due to high pH), sweating, rash.
Hazard Codes: T
Risk Statements: 46-60-61
R46:May cause heritable genetic damage.
R60:May impair fertility.
R61:May cause harm to the unborn child.
Safety Statements: 53-36/37/39-45
S53:Avoid exposure - obtain special instructions before use.
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
WGK Germany: 3
RTECS of Ganciclovir (CAS NO.82410-32-0): MF8407000
6. Use of Ganciclovir
Ganciclovir (CAS NO.82410-32-0) is an antiviral medication used to treat or prevent cytomegalovirus (CMV) infections.
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