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CAS No. : | 892-48-8 | MDL No. : | MFCD00049038 |
Formula : | C10H12ClN5O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | IYSNPOMTKFZDHZ-KQYNXXCUSA-N |
M.W : | 285.69 | Pubchem ID : | 5327118 |
Synonyms : |
|
Num. heavy atoms : | 19 |
Num. arom. heavy atoms : | 9 |
Fraction Csp3 : | 0.5 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 6.0 |
Num. H-bond donors : | 3.0 |
Molar Refractivity : | 66.31 |
TPSA : | 119.31 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) : | -8.09 cm/s |
Log Po/w (iLOGP) : | 0.98 |
Log Po/w (XLOGP3) : | -0.06 |
Log Po/w (WLOGP) : | -1.05 |
Log Po/w (MLOGP) : | -1.65 |
Log Po/w (SILICOS-IT) : | -1.25 |
Consensus Log Po/w : | -0.61 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.79 |
Solubility : | 4.61 mg/ml ; 0.0161 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.99 |
Solubility : | 2.89 mg/ml ; 0.0101 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -0.78 |
Solubility : | 47.9 mg/ml ; 0.167 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 3.96 |
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 |
---|---|---|
89% | With thionyl chloride In N,N,N,N,N,N-hexamethylphosphoric triamide; water | EXAMPLE 2 Preparation of 5'-deoxy-5'-ethylthioadenosine 1 kg of adenosine is dissolved under a nitrogen atmosphere in 10 l of hexamethylphosphoramide, and 7.5 l of thionyl chloride are added under cooling. The mixture is left to react at ambient temperature for 20 hours. 10 l of water are added, and the mixture neutralised with 2 N NaOH. The 5'-deoxy-5'-chloroadenosine which thus forms is allowed to crystallise overnight at 3° C. It is filtered off. 0.950 kg of 5'-deoxy-5'-chloroadenosine are obtained (yield 89percent). |
86% | Stage #1: With pyridine; thionyl chloride In acetonitrile at 0 - 5℃; Stage #2: With ammonium hydroxide In methanol; water; acetonitrile at 20℃; for 0.5 h; |
Compound 308l-(3-((((2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2- yl)methyl)thio)propyl)-3-(4-(tert-butyI)phenyl)ureaStep 1. (2R,3R,4S,5S)-2-(6-amino-9H-purin-9-yl)-5- (chloromethyl)tetrahydrofuran-3,4-diol To a solution of (2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5- (hydroxymethyl)tetrahydrofuran-3,4-diol (1 g, 3.47 mmol) in pyridine (593 mg, 0.6 ml, 7.49 mmol) in acetonitrile (10ml) cooled in an ice bath was added SOCl2 (2.22g, 1.36ml,18.65mmol). Stirring was continued at 0-5° C for 3-4 h, and warning to ambient temperature for overnight. The resulting suspension was concentrated in vacuo. To the reaction mixture was added methanol (20 ml), water (2ml), and NH4OH (4 ml), followed by stirring for 0.5 h at room temperature. The reaction mixture was concentrated to dryness. The compound was dissolved in MeOH, silica gel (3g) was added and then solvent was removed. The residue was purified by SGC to elute with EA : MeOH (0percent-10percent) to obtain the title compound (0.915 g, yield 86percent) as yellowish solid. NMR (500 MHz, MeOD): δ 8.24 (s, 1H), 8.02 (s, 1H), 7.27-7.20 (m, 5H), 6.19 (d, J = 2.0 Hz, 1H), 5.48-5.46 (m, 1H), 5.08-5.06 (m, 1H), 4.43 (t, J = 4.0, Hz, 1H), 3.83- 3.81 (m, 2H). |
86% | Stage #1: With pyridine; thionyl chloride In acetonitrile at 0 - 5℃; Stage #2: With ammonium hydroxide In methanol; water; acetonitrile at 20℃; for 0.5 h; |
((3aS,4S,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2 dimethyltetrahydro furo[3,4- d][l,3]dioxol-4-yl)methanethiolStep 1. Preparation of (2R,3R,4S,5S)-2-(6-amino-9H-purin-9-yl)-5- (chloromethyl) tetrahydrofuran-3,4-diolTo a solution of (2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5- (hydroxymethyl)tetrahydrofuran-3,4-diol (1 g, 3.47 mmol) in pyridine (593 mg, 0.6 ml, 7.49 mmol) in acetonitrile (10ml) cooled in an ice bath was added SOCl2 (2.22g, 1.36ml,18.65mmol). Stirring was continued at 0-5° C for 3-4 h, and warning to ambient temperature for overnight. The resulting suspension was concentrated in vacuo. To this reaction mixture was added methanol (20 ml), water (2ml), and NH4OH (4 ml), followed by stirring for 0.5 h at room temperature. The reaction mixture was concentrated to dryness. The compound was dissolved in MeOH, silica gel (3g) was added and then solvent was removed. The residue was purified by SGC to elute with EA : MeOH (0percent-10 ) to obtain the target compound (0.915 g, yield 86percent) as yellowish solid. NMR (500 MHz, MeOD): δ 8.24 (s, IH), 8.02 (s, IH), 7.27-7.20 (m, 5H), 6.19 (d, / = 2.0 Hz, IH), 5.48-5.46 (m, IH), 5.08-5.06 (m, IH), 4.43 (t, J = 4.0, Hz, IH), 3.83- 3.81 (m, 2H), 3.01-2.99 (br s, 2H), 1.60 (s, 3H), 1.38 (s, 3H) ppm, LCMS (m/z): 395.8 [M+H]+. |
60% | Stage #1: With pyridine; thionyl chloride In acetonitrile at 0 - 20℃; Stage #2: With ammonium hydroxide In methanol; water at 20℃; for 0.5 h; |
To a cold suspension (0°С) of adenosine (3.0 g, 11.2 mmol) in acetonitrile (35 ml) and pyridine (22.4 mmol, 1.8 ml), thionyl chloride (4.1 ml, 56.1 mmol) was slowly added and the mixture was stirred 4 h under 0°С. The resulting solution was kept at ambient temperature overnight. The precipitate was filtered and dissolved in H2O/MeOH (5:50 ml) and 25percent aqueous ammonia (4.7 ml) was added to the mixture. The reaction mixture was kept at ambient temperature for 30 min and evaporated in vacuum. The residue was transferred to a glass filter, washed with cold water (2 * 20 ml) and dried in vacuum desiccator over P2O5. Yield 1.92 g (60percent) as white crystals. Rf 0.15 (CH2Cl2-EtOH, 9:1 v/v). 1H NMR (DMSO-d6): δ = 3.84 (dd, 1H, J5'b-4' = 6.3 Hz, J5'ba = -11.6 Hz, H5'b), 3.94 (dd, 1H, J5'a-4' = 5.1 Hz, J5'ab = -11.6 Hz, H5'a), 4.10 (ddd, 1H, J4'-5'b = 6.3 Hz, J4'-5'a = 5.1 Hz, J4'-3' = 4 Hz, H4'), 4.23 (ddd, 1H, J3'-4' = 4 Hz, J3'-OH = 5.1 Hz, J3'-2' = 5 Hz, H3'), 4.75 (dd, 1H, J2'-3' = 5 Hz, J2'-1' = 5.6 Hz, H2'), 5.41 (d, 1H, JOH-3' = 5.1 Hz, 3'OH), 5.56 (d, 1H, JOH-2' = 6.03 Hz, 2'OH), 5.93 (d, 1H, J1'-2' = 5.6 Hz, H1'), 7.26 (s, 2H, NH2), 8.15 (s, 1H, H8), 8.33 (s, 1H, H2). |