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CAS No. : | 52522-49-3 | MDL No. : | MFCD00038477 |
Formula : | C33H31NO8 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | VBDBDZHLJKDSSB-UFRUDBOASA-N |
M.W : | 569.60 | Pubchem ID : | 97076 |
Synonyms : |
|
Num. heavy atoms : | 42 |
Num. arom. heavy atoms : | 24 |
Fraction Csp3 : | 0.24 |
Num. rotatable bonds : | 14 |
Num. H-bond acceptors : | 8.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 155.88 |
TPSA : | 109.04 Ų |
GI absorption : | Low |
BBB permeant : | No |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | Yes |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | Yes |
Log Kp (skin permeation) : | -5.78 cm/s |
Log Po/w (iLOGP) : | 4.32 |
Log Po/w (XLOGP3) : | 5.63 |
Log Po/w (WLOGP) : | 5.41 |
Log Po/w (MLOGP) : | 2.81 |
Log Po/w (SILICOS-IT) : | 3.67 |
Consensus Log Po/w : | 4.37 |
Lipinski : | 1.0 |
Ghose : | None |
Veber : | 1.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -6.42 |
Solubility : | 0.000218 mg/ml ; 0.000000383 mol/l |
Class : | Poorly soluble |
Log S (Ali) : | -7.68 |
Solubility : | 0.0000118 mg/ml ; 0.0000000207 mol/l |
Class : | Poorly soluble |
Log S (SILICOS-IT) : | -9.52 |
Solubility : | 0.000000171 mg/ml ; 0.0000000003 mol/l |
Class : | Poorly soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 3.0 |
Synthetic accessibility : | 5.31 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-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 |
---|---|---|
With sodium borohydrid; In methanol; dichloromethane; water; isopropyl alcohol; acetonitrile; | EXAMPLE 6 Synthesis of 9-beta-D-Arabinofuranosyl-2-fluoroadenine A solution of 2,3,5-tri-O-benzyl-1-alpha-D-arabinofuranosylchloride (freshly prepared from 1.9 g of 2,3,5-tri-O-benzyl-1-O-p-nitrobenzoyl-D-arabinofuranose) and 6-azido-2-fluoropurine (0.50 g) in anhydrous acetonitrile (30 mL) was stirred for 1 hour at room temperature and then 3 A molecular sieve (1.26 g, pellets) was added. The mixture was stirred under an inert atmosphere for 3 days and then filtered. The filtrate was concentrated under reduced pressure and the residue was dissolved in 2-propanol and methanol, and then sodium borohydride (0.13 g) was added. After stirring overnight at room temperature the resulting precipitate was collected by filtration. The precipitate was washed with 2-propanol followed by boiling water and then dried to obtain 0.14 g of the title compound. The organic filtrates were concentrated under reduced pressure and the residue was partitioned between dichloromethane and water. The dichloromethane solution was dried over MgSO4 and then filtered and placed on a silica gel column. Elution with 1% methanol in dichloromethane provided an additional 0.10 g of the title compound. Both samples were identical by IR and TLC to an authentic sample of the title compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-ethyl-N,N-diisopropylamine; In hexane; ethyl acetate; 1,2-dichloro-ethane; | EXAMPLE 3 Synthesis of 6-Azido-2-fluoro-9-(2,3,5-tri-O-benzyl-beta-D-arabinofuranosyl)purine A solution of 2,3,5-tri-O-benzyl-1-alpha-D-arabinofuranosylchloride (freshly prepared from 1.9 g of <strong>[52522-49-3]2,3,5-tri-O-benzyl-1-O-p-nitrobenzoyl-D-arabinofuranose</strong>), N,N-diisopropylethylamine (0.58 mL) and 6-azido-2-fluoropurine (0.50 g) in 10 mL of anhydrous 1,2-dichloroethane was heated at reflux overnight. Additional N,N-diisopropylethylamine (0.26 mL) was added and heating was continued for an additional 24 hours. The mixture was cooled to ambient temperature and diluted with dichloromethane (60 mL) and washed sequentially with 10% aqueous sodium hydroxide (NaOH), water, 1N phosphoric acid (H3 PO4), saturated NaCl and then dried over MgSO4 along with decolorizing carbon. The dried solution was filtered through celite and concentrated in vacuo. The residue was purified by silica gel chromatography with gradient elution from 3:1 Hexane:ethyl acetate to 100% ethyl acetate to obtain 0.40 g of the title compound as a colorless oil; IR (neat) 3031, 2922, 2867, 2126, 1608 cm-1; 1 H NMR (DMSO-d6, 360 MHz) delta3.65-3.75 (m, 2H), 4.16 (q, J=5 Hz, 1H), 4.22 (d, J=11.8 Hz), 4.42 (t, J=5.5 Hz, 1H), 4.47 (d, J=11.8 Hz, 1H), 4.51 (s, 2H), 4.58 (t, J=5.5 Hz, 1H), 4.62 (d, J=12.0 Hz, 1H), 4.68 (d, J=12.0 Hz, 1H), 6.41 (d, J=5.5 Hz, 1H), 6.9-6.95 (m, 2H) 7.1-7.2 (m, 3H), 7.25-7.4 (m, 10H), 8.48 (s, 1H); UV (MeOH) lambdamax, 286 nm; MS (EI+, m/z) 582 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1.6 g (95.0%) | With NaH; In acetonitrile; | 2,5,6-Trichloro-1-(2,3,5-tri-O-benzyl-beta-D-arabinofuranosyl)benzimidazole (133) Compound 5 (598 mg 2.7 mmole) was dissolved in dry CH3 CN(60 ml) and 97% NaH (80 mg, 3 mmole) was added. The mixture was stirred under N2 for 1 hour at room temperature. Then 2,3,5-tri-O-benzyl-D-arabinofuranoxyl chloride (prepared from <strong>[52522-49-3]2,3,5-tri-O-benzyl-1-O-p-nitrobenzoyl-D-arabinofuranose</strong>) (1.83 g, 3 mmole)) dissolved in dry CH3 CN (20 ml) was added dropwise. The mixture was stirred under N2 for overnight at room temperature. The reaction solution was filtered through Celite. The filtrate was evaporated to give a syrup and this syrup was subjected to flash column chromatography on silica gel (Kieselgel 60, 230-400 mesh) and eluted with CH2 Cl2. The fractions containing 133 were combined and evaporated to give 1.6 g (95.0%) of 133. (IR KBr cm-1: 1140-1060 (C--O--C)). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1.6 g (95.0%) | With NaH; In acetonitrile; | 2,5,6-Trichloro-1-(2,3,5-tri-O-benzyl-beta-D-arabinofuranosyl)benzimidazole (133) Compound 5 (598 mg 2.7 mmole) was dissolved in dry CH3 CN (60 ml) and 97% NaH (80 mg, 3 mmole) was added. The mixture was stirred under N2 for 1 hour at room temperature. Then 2,3,5-tri-O-benzyl-D-arabinofuranosyl chloride (prepared from <strong>[52522-49-3]2,3,5-tri-O-benzyl-1-O-p-nitrobenzoyl-D-arabinofuranose</strong>) (1.83 g, 3 mmole)) dissolved in dry CH3 CN (20 ml) was added dropwise. The mixture was stirred under N2 for overnight at room temperature. The reaction solution was filtered through Celite. The filtrate was evaporated to give a syrup and this syrup was subjected to flash column chromatography on silica gel (Kieselgel 60, 230-400 mesh) and eluted with CH2 Cl2. The fractions containing 133 were combined and evaporated to give 1.6 g (95.0%) of 133. (IR KBr cm-1: 1140-1060 (C--O--C)). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
molecular sieve; In dichloromethane; 1,2-dichloro-ethane; benzene; | Dry hydrogen chloride gas was bubbled into a solution of <strong>[52522-49-3]2,3,5-tri-O-benzyl-1-O-p-nitrobenzoyl-D-arabinofuranose</strong> (121 g., 212 mmoles) in methylene chloride (1.33 l at -10 to 0 for 2.5 hours. The precipitated p-nitrobenzoic acid was removed by filtration and washed with methylene chloride. The methylene chloride solution was evaporated in vacuo. The residue, dissolved in 1 l. of ethylene chloride, was added to a mixture of 2,6-diacetamidopurine (50.0 g., 213 mmoles) and molecular sieve (Linde 4A, 630 g.) in 6 l. of ethylene chloride. This mixture was refluxed until all the chlorosugar was consumed (tlc) (5 days). The mixture was then stirred with Celite and filtered. The solid was washed with chloroform and the combined filtrates were evaporated to dryness in vacuo. The residue was dissolved in benzene and filtered (to remove unreacted 2,6-diacetamidopurine). The filtrate was again evaporated to dryness in vacuo, producing 2,6-diacetamido-9-(2,3,5-tri-O-benzyl-beta-D-arabinofuranosyl)adenine (4). The residue dissolved in 700 ml. of 1 N methanolic sodium methoxide. After a 3-hour reflux period, the solution was chilled, neutralized with acetic acid, and refrigerated overnight. The solid that precipitated was removed by filtration, washed with methanol, and dried in vacuo; yield 47 g. (40%); m.p. 160-163; tlc homogeneous (19:1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
4-Amino-6-fluoro-1(2,3,5-tri-O-benzyl-beta-D-arabinoffiinosyl)imidazo[4,5-c]pyridine (41) and 4-amino-6-fluoro-1-(2,3,5-tri-O-benzyl-alpha-D-arabinofuranosyl)imidazo[4,5-c]pyridine (42). A mixture of 4,6-difluoroimidazo[4,5-c]pyridine (34, 0.5 g, 3.2 mmol) and ammonium sulfate (a catalytic amount) in hexamethyldisilazane (15 mL) was refluxed for 2 h. The resulting clear solution was cooled and concentrated in vacuo under anhydrous conditions to dryness. The residue was dissolved in 15 mL of dichloroethane, followed by addition of <strong>[52522-49-3]1-O-(4-nitrobenzoyl)-2,3,5-tri-O-benzyl-D-arabinofuranose</strong> (2 g, 3.6 mmol) and TMSOTf (1 mL) and the reaction mixture was refluxed with stirring under nitrogen for 2 h. The reaction mixture was cooled and stirred with saturated sodium bicarbonate solution (15 mL) for 10 min at room temperature. The organic layer was separated and the aqueous layer was extracted with methylene chloride (30 mL×2). The combined organic layer was washed with saturated sodium bicarbonate solution, then water and dried (anhydrous MgSO4). After filtration, the filtrate was concentrated in vacuo and the residue was purified by silica gel column chromatography (CH2Cl2/EtOAc, 20:1, v/v) to yield 40 (1.2 g, 67%) as a syrup. NMR showed it to be a mixture of alpha- and beta-anomers. Compound 40 (1.1 g, 2.0 mmol) was dissolved in 60 mL of ethanol, saturated with anhydrous ammonia and heated in a stainless steel bomb at 100-105 C. overnight. The reaction mixture was cooled, evaporated to dryness and separated by silica gel column chromatography (CH2Cl2/EtOH, 20:1, v/v) to yield 41 (0.30 g, 27%), 42 (0.34 g, 31%) and a mixture of 41 and 42 (0.17 g, 15%). [0173] Compound 41 was isolated as a white foam: TLC, Rf 0.63 (CH2Cl2/EtOH, 20:1, v/v); 1H NMR (CDCl3) delta 3.70 (m, 2H, 5'-H), 4.10 (m, 1H, 4'-H), 4.25 (m, 2H, 2'- and 3'-H), 4.65 (s, 6H, ArCH2), 5.75 (br s, 2H, NH2, D2O exchangeable), 5.96 (d, 1H, 1'-H, J=5 Hz), 6.14 (s, 1H, 7-H), 6.80-7.40 (m, 15H, ArH), 8.01 (s, 1H, 2-H). Analysis calculated for C32H31FN4O4: C, 69.28; H, 5.63; N, 10.10. Found: C, 69.10; H, 5.40; N, 9.96. [0174] Compound 42 was isolated as a white foam: TLC, Rf 0.53 (CH2Cl2/EtOH, 20:1, v/v); 1H NMR (CDCl3) delta 3.58 (m, 2H, 5'-H), 4.25 (m, 1H, 4'-H), 4.30 (m, 2H, 2'- and 3'-H), 4.50 (s, 6H, ArCH2), 5.60 (br s, 2H, NH2, D2O exchangeable), 5.85 (d, 1H, 1'-H, J=5.2 Hz), 6.20 (s, 1H, 7-H), 7.00-7.40 (m, 15H, ArH), 7.84 (s, 1H, 2-H). Analysis calculated for C32H31FN4O40.05EtOH: C, 69.01; H, 5.67; N, 10.06. Found: C, 68.87; H, 5.30; N, 9.98. |
Tags: 52522-49-3 synthesis path| 52522-49-3 SDS| 52522-49-3 COA| 52522-49-3 purity| 52522-49-3 application| 52522-49-3 NMR| 52522-49-3 COA| 52522-49-3 structure
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