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CAS No. : | 69-89-6 | MDL No. : | MFCD00078453 |
Formula : | C5H4N4O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | LRFVTYWOQMYALW-UHFFFAOYSA-N |
M.W : | 152.11 | Pubchem ID : | 1188 |
Synonyms : |
2,6-Dihydroxypurine;NSC 14664
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 9 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 3.0 |
Molar Refractivity : | 37.34 |
TPSA : | 94.4 Ų |
GI absorption : | High |
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) : | -7.75 cm/s |
Log Po/w (iLOGP) : | 0.07 |
Log Po/w (XLOGP3) : | -0.73 |
Log Po/w (WLOGP) : | -1.06 |
Log Po/w (MLOGP) : | -1.25 |
Log Po/w (SILICOS-IT) : | 1.46 |
Consensus Log Po/w : | -0.3 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -0.93 |
Solubility : | 17.9 mg/ml ; 0.118 mol/l |
Class : | Very soluble |
Log S (Ali) : | -0.78 |
Solubility : | 25.5 mg/ml ; 0.167 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -1.96 |
Solubility : | 1.66 mg/ml ; 0.0109 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.71 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H317-H319 | 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 |
---|---|---|
18.4 g | With bromine In water at 100℃; | Take xanthine 15g, was added 250mL ofwater, 7.6mL bromine, and heated to 100 ° C, i.e. the bromine color disappearsto stop the reaction, washed with a small amount of water, the reaction mixturewas cooled to room temperature, suction filtered, the filter cake was dried invacuo , the products 18.4g; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.78 g (8.2%) | A. 1-(4-Chlorobenzyl)-3-ethyl-8-isopropyl-xanthine 3.17 g (28.2 mM) of potassium t-butoxide (t-BuOK) were added to a solution of 6.11 g (27.5 mM) of 6-amino-1-ethyl-5-isobutyrylamino-uracil. At 0 C., 4.90 g (30.4 mM) of 4-chlorobenzylclhloride were added. After 3 hours at 0-5 C., further 1.22 g t-BuOK and 2.45 g of 4-chloro-benzylchloride were added. After further 3 hours another 2.45 g of benzylchloride are supplemented. After 3 days, the solution was neutralized with 1N HCl and the solvents evaporated. The residue was suspended in water, the solid collected and washed. The crude intermediate amide was heated under reflux in 100 ml of 1N NaOH and 10 ml of 1-propanol. After 1 hour, the mixture was neutralized to pH 7 and extracted with chloroform. Crystallization from dichloromethane (mainly evaporated)--methanol gave 2.99 g (31.3%) of the title xanthine, mp 194-5 C. The mother liquors gave 6.33 g of impure material which was separated on 15 g of silica gel elutions with dichloromethane and gave additional 0.78 g (8.2%) of the xanthine. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
6.80 g (98.7%) | With diphosphorus pentasulfide; In pyridine; sodium hydroxide; water; isopropyl alcohol; | 6.59 g (19 mM) of <strong>[69-89-6]xanthin</strong>e and 5.07 g (22.8 mM) of phosphorus pentasulfide were heated under reflux in 102 ml of pyridine for 3 days. At 0 C., 25.1 ml of 2N NaOH were added. The solid was filtered off and washed with pyridine. The solvents were evaporated in vacuo, the residue suspended in water, collected, redissolved in 100 ml of 1N NaOH and 50 ml of isopropanol, treated twice with 0.3 g of charcoal, filtered and neutralized with 5N HCl to pH 7. The isopropanol was removed in vacuo and the solid collected, washed and dried to give 6.80 g (98.7%) of 6-thio<strong>[69-89-6]xanthin</strong>e, mp 188-9 C. Elemental analysis for C17 H19 Cl N4 OS: Calculated: C 56.27 H 5.28 N 15.44 0 4.41 Found: C 56.25 H 5.33 N 15.47 0 4.41 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
9.2 g (60%) | In sodium hydroxide; (CH2)3 COOEt; N,N-dimethyl-formamide; | EXAMPLE 2 1-(4-hydroxybutyl)-3-butyl xanthine (Method B, xanthine no. 21) 11.3 g (0. 05 mole) of 1-butyl-5-formylamino-6-aminouracil (II) (R1 =butyl, R8 =H) are dissolved under nitrogen in 200 ml of DMF. 10.6 ml (0.075 mole) of ethyl 4-bromobutyrate are added, after which 2 g (0.05 mole) of solid powder-form NaOH is added with thorough stirring in portions of 0.5 g at intervals of 1 hour. On completion of the addition, the mixture is left to react overnight. The solvent is then evaporated and the oily residue of (IV) (substituent in the 1-position=(CH2)3 COOEt) is dissolved in 100 ml of 10% NaOH. This solution is then heated under reflux for 0.5 hour and then cooled, neutralized to pH 5 with acetic acid and filtered. The precipitate formed is dried. Yield: 9.2 g (60%) of crude xanthine (V) (substituent in the 1-position=(CH2)3 COOH, R3 =butyl, R8 =H). |
9.2 g (60%) | In sodium hydroxide; N,N-dimethyl-formamide; | EXAMPLE 2 1-(4-Hydroxybutyl)-3-butylxanthine (Method B, compound No. 21) 11.3 g (0.05 mole) of 1-butyl-5-formylamino-6-aminouracil (II) (R3 =butyl, R2 =H) are dissolved under nitrogen in 200 ml of DMF. 10.6 ml (0.075 mole) of ethyl 4-bromobutyrate are added, followed, with good stirring, by 2 g of (0.05 mole) of powdered solid NaOH in hourly 0.5 g portions. When the addition has been completed, the mixture is left to react overnight again. The solvent is evaporated off and the oily residue of (IV) (substituent in the 1 position=--(CH2)3 COOEt) is dissolved in 100 ml of 10% NaOH. This solution is refluxed for 1/2 hour. It is cooled, neutralized with acetic acid to pH 5, and the precipitate formed is filtered off and dried. Yield: 9.2 g (60%) of crude xanthine (V) (substituent in the 1 position=--(CH2)3 COOH, R3 =butyl, R2 =H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In dichloromethane; | This is done for example by the following procedure: 0.2 g of 3-isobutyl-1-methylxanthine (IBMX), 3.6 g of soya lecithin and 0.4 g of beta-sitosterol are dissolved in 25 ml of methylene chloride. This organic solution is evaporated in a rotating round-bottomed flask at 45 C. under reduced pressure to give a lipidic film deposited on the inner wall of the flask. The film obtained is taken up in 95.8 g of distilled water or buffer solution to give a suspension of lipidic vesicles. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With bromine; In water; at 100℃; for 2h; | EXAMPLE 15 8-{4-[2-(Tnfluoromethyl')phenoxy]pphiendin-l-vU-3,9-dihvdro-lH-pu?ne-2,6-dione Step 1: 8-bromo-3,9-dihvdro-lH-purine-2,6-dione To a mixture of <strong>[69-89-6]xanthin</strong>e (100 mg, 0.66 mmol) in water (0.65 mL) was added bromine (0.05 mL, 0.99 mmol) m a 4-mL glass vial. The vial was capped and heated at 1000C. After 2 h, the mixture was cooled to room temperature, filtered and the solid washed with water and then Et2O. The product was dried under high vacuum to give the title product as a solid. leta NMR (500 MHz, DMSO-d6): delta 14.09 (1 H, s), 11.64 (1 H, s), 10.91 (1 H, s). MS (+ESI) m/z 232, 233 (MH+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Example 8 5-[8-(4-Acetylamino-benzyl)-1-benzyl-2,6-dioxo-1,2,6,7-tetrahydro-purin-3-ylmethyl]-furan-2-carboxylic acid; compound with trifluoro-acetic acid This compound was prepared by a method similar to that described in example 5 except that 5-chloromethyl-furan-2-carboxylic acid methyl ester was used in place of 3-bromomethylfuran. The methyl ester was hydrolyzed to the carboxylic acid during cyclization to form the xanthine. MS, m/z(M+)=513.1654. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
13.4% | (2,6-Dioxo-1,2,3,6-tetrahydro-purin-7-yl)-acetic acid (131) <strong>[69-89-6]Xanthin</strong>e (4.8 g, 31.5 mmol) was suspended in water and 2 M sodium hydroxide (50 mL) and the resulting suspension was stirred for 30 min. Chloroacetic acid (3 g, 31.5 mmol) was then added. The resulting solution was refluxed for 5 h, cooled to room temperature and stirred overnight. The precipitate was filtered and the aqueous solution was then acidified (pH 3) with 12 M HCl. The resulting precipitate was filtered and then washed with hot EtOH and then hot hexanes to yield a mixture of crude products 131 and 132. Water (65 mL) was added to these crude products and the resulting mixture was refluxed for 30 min. The solution was hot filtered and the precipitate was collected. The precipitate was then washed with hot ethanol and hexanes to yield 131 as a white solid (0.9 g, 13.4%). | |
Commercially available lH-purine-2,6(3H,7H)-dione (1 equiv.) in water (1.5 M) at room temperature was added 2M NaOH solution (0.65 M) and the resulting solution was stirred for 30 min and chloroacetic acid (1 equiv.) was added and resulting reaction mixture was refluxed for 5 h. The reaction mixture was cooled to room temperature and stirred for 16 h. The precipitated solid was removed by filtration and water was acidified with cone HC1 (pH 2). The solid collected by filtration, washed with hot ethanol to afford the intermediate 2-(2,6-dioxo-2,3- dihydro-lH-purin-7(6H)-yl)acetic acid as a white solid. 1H NMR (400 MHz, DMSO-d6) delta (ppm): 13.35 (brs, 1H), 11.59 (s, 1H), 10.88 (brs, 1H), 7.91(s, 1H), 5.0 (s, 2H). LC-MS: m/z +H) with a purity of 97%. |
Tags: 69-89-6 synthesis path| 69-89-6 SDS| 69-89-6 COA| 69-89-6 purity| 69-89-6 application| 69-89-6 NMR| 69-89-6 COA| 69-89-6 structure
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