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CAS No. : | 86357-14-4 | MDL No. : | MFCD08457700 |
Formula : | C15H19N5O7 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | PEZKHGVZZSQDPY-UHFFFAOYSA-N |
M.W : | 381.34 | Pubchem ID : | 135427290 |
Synonyms : |
|
Num. heavy atoms : | 27 |
Num. arom. heavy atoms : | 9 |
Fraction Csp3 : | 0.47 |
Num. rotatable bonds : | 11 |
Num. H-bond acceptors : | 9.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 91.03 |
TPSA : | 154.5 Ų |
GI absorption : | Low |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -9.26 cm/s |
Log Po/w (iLOGP) : | 0.69 |
Log Po/w (XLOGP3) : | -0.89 |
Log Po/w (WLOGP) : | -0.8 |
Log Po/w (MLOGP) : | -0.71 |
Log Po/w (SILICOS-IT) : | 0.31 |
Consensus Log Po/w : | -0.28 |
Lipinski : | 1.0 |
Ghose : | None |
Veber : | 2.0 |
Egan : | 1.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.16 |
Solubility : | 26.1 mg/ml ; 0.0685 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.87 |
Solubility : | 5.12 mg/ml ; 0.0134 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.73 |
Solubility : | 0.71 mg/ml ; 0.00186 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 3.2 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With acetic acid In water; methylamine | Example 8 Preparation of 9-(1,3-dihydroxy-2-propoxymethyl)guanine 12 and 7-(1,3-dihydroxy-2-propoxymethyl)guanine 11 Compound 9 (8.0 g) was dissolved in 100 ml of aqueous methylamine (40percent) and gently refluxed for 1.5 hours, and then was evaporated to dryness to give a white solid. The solid was crystallized from 50 ml of water and 10 drops of acetic acid (to neutralize amine and remove the color) to give a white crystalline product 12 (4.63 g, 87percent). mp>300° (dec.); Rf 0.62 (CH3 OH:CHCl3 =1:1); UV (H2 O) pH7 λmax 251.5 (ε 10180), 272.0 (sh, ε 7500), pH2 λmax 253.5 (ε9840), pH 11 λmax 265.6 (ε 8060); 1 H NMR (DMSO-d6) δ 10.64 (s, 1H, AcNH, D2 O exchangeable), 7.80 (s, 1H, 8-H), 6.49 (s, 2H, NH2 D2 O exchangeable), 5.43 (s, 2H, 1'-H), 4.61 (t, 2H, OH, D2 O exchangeable), 3.55-3.28 (m, 5H, 4'-H, 5'-H, 3'-H). |
82.8% | at 70℃; for 0.5 h; Microwave irradiation | In the second step, the above-mentioned triacetyl ganciclovir compound (2) 67.1 g and 10percent potassium hydroxide solution 200 g are put into a microwave reactor.The temperature was raised to 70 ° C for 0.5 hour, cooled to room temperature, sulfuric acid was added to adjust the pH to neutrality, 3.3 g of activated carbon was added, and then dissolved.The mixture was decolorized by reflux at elevated temperature for 1 hour, filtered, and the filtrate was cooled to 10 ° C for crystallization.Filtration and drying gave 37.5 g of crude ganciclovir, the yield was 84.2percent, and the purity was 97.1percent. In the third step, 37.5 g of crude ganciclovir and 187 g of DMF were added to the reaction flask, and the mixture was heated to 90 ° C until stirred.Then cooled to 40 ° C, added 561g of methanol, and continued to cool to 20 ° C for 5 hours.Filtration, methanol washing, drying to obtain pure ganciclovir 31.0g, yield 82.8percent, purity 99.0percent, |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85.3% | With boron trifluoride diethyl etherate In N,N-dimethyl-formamide at 100℃; for 10 h; Microwave irradiation | In the first step, 20.0-diacetylguanine 50.0 g (0.21 mol, 1.0 eq), 1,3-diacetoxy-2-(acetoxymethoxy)propane 104.2 g (0.42 mol, 2.0 eq ),3.0 g (0.021 mol, 0.1 eq) of boron trifluoride etherate and 200 g of N,N-dimethylformamide were placed in a microwave reactor, and the mixture was heated to 100 ° C for 10 hours.The solvent was distilled off under reduced pressure, and the mixture was cooled to room temperature. 450 g of ethyl acetate was added and refluxed for 1 hour, and the temperature was lowered to 0 to 5 ° C for 1 hour.After suction filtration and drying, the triacetyl ganciclovir compound (2) 68.3 g, the yield was 85.3percent,The purity was 95.6percent, and the compound (3) was 3.1percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
46.7% | With phosphoric acid In chloroform; N,N-dimethyl-formamide | Example 7 Preparation of 9-[2-Acetoxy-1-(acetoxymethyl)ethoxy]methyl}-2-acetamidopurine-6-one (9) and 7-[2-acetoxy-1-(acetoxymethyl)ethoxy]methyl}-2-acetaminopurine-6-one (10) A mixture of diacetylguanine (10.575 g, 45 mmol), 2-acetoxymethoxy-1,3-diacetoxypropane (22.32 g, 90 mmol) and phosphoric acid (0.3 ml) in DMF (45 ml) was heated for three hours at 120° (oil bath 135°) with stirring. The suspension gradually became homogeneous. When TLC indicated the reaction was complete, the reaction solution was evaporated in vacuo to remove solvents yielding a dark-brown syrup. The syrup was dissolved in small amount of CHCl3 and applied to a column (silica gel 60, φ4*27 cm), eluted with CH3 OH:CHCl3 (0-3percent) to give 9 (8.0 g, 46.7percent) and 10 (5.1 g, 29.8percent). Compound 9: mp 165°-7° (ethyl acetate); Rf 0.49 (CH3 OH--CHCl3 =1:9); UV (CH3 OH) λmax 254.5, 278.0 (sh); 1 H NMR (DMSO-d6) δ 12.07, 11.78 (NH, s, 2H, D2 O exchangeable), 8.14 (s, H, 8-H), 5.53 (s, 2H, OCH2 N), 4.11-3.94 (m, 5H, (OCH2 CH)2 CH), 2.18 (s, 3H, AcN), 1.88 (s, 6H, AcO). Compound 10: mp 176°-178°; Rf 0.61 (CH3 OH:CHCl3 =1:9); UV (CH3 OH) λmax 261.5 nm; 1 H NMR (DMSO-d6) δ 12.18, 11.63 (s, 2H, NH, D2 O exchangeable), 8.38 (s, 1H, 8-H), 5.73 (s, 2H, OCH2 N), 4.14-3.92 (m, 5H, (OCH2 CH)2 CH), 2.17 (s, 3H, AcN), 1.88 (s, 6H, AcO). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | for 6 h; Reflux | Ganciclovir (1.0 g, 4.0 mmol), acetic anhydride (5.0 ml, 53 mmol), and pyridine (10.0 ml) were heated together, under reflux, for 6 hours. Initially, the reaction mixture was not homogeneous but once reaction completed, all were in the solution. The reaction was cooled, treated with methanol (5.0 ml), stirred for 30 minutes at 25° C., and then concentrated under reduced pressure. The crude gummy product was purified by silica gel column chromatography using 4-6percent methanol/ dichloromethane 4 to provide tri-acetylated ganciclovir, 2 (1.2 g, 3.14 mmol, yield 80percent) as a colorless powdered. 1H NMR (CDCl3, 400 MHz): δ 12.02 (s, 1H), 9.49 (s, 1H), 7.84 (s, 1H), 5.55 (s, 2H), 4.19 (t, J=4.0 Hz, 4H), 4.12 (m, 1H), 2.35 (s, 3H), 2.05 (s, 6H). ESI-LC/MS: Expected [M+H]+ for C15H19N5O7 is 382.13, found m/z: 382.37 [M+H]+. |
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