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CAS No. : | 550-33-4 | MDL No. : | MFCD00022819 |
Formula : | C10H12N4O4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | MRWXACSTFXYYMV-FDDDBJFASA-N |
M.W : | 252.23 | Pubchem ID : | 68368 |
Synonyms : |
Desaminoadenosine;Ribosylpurine;Purinosine;Purine riboside;NSC 65423
|
Num. heavy atoms : | 18 |
Num. arom. heavy atoms : | 9 |
Fraction Csp3 : | 0.5 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 7.0 |
Num. H-bond donors : | 3.0 |
Molar Refractivity : | 58.27 |
TPSA : | 113.52 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) : | -8.34 cm/s |
Log Po/w (iLOGP) : | 1.02 |
Log Po/w (XLOGP3) : | -0.7 |
Log Po/w (WLOGP) : | -1.89 |
Log Po/w (MLOGP) : | -2.21 |
Log Po/w (SILICOS-IT) : | -1.66 |
Consensus Log Po/w : | -1.09 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.2 |
Solubility : | 15.9 mg/ml ; 0.063 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.21 |
Solubility : | 15.6 mg/ml ; 0.0618 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | 0.05 |
Solubility : | 281.0 mg/ml ; 1.11 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 3.69 |
Signal Word: | Warning | Class: | |
Precautionary Statements: | P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313 | UN#: | |
Hazard Statements: | H315-H319 | Packing Group: | |
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 palladium on activated charcoal; water; magnesium oxide Hydrogenation; | ||
With palladium 10% on activated carbon; hydrogen; potassium carbonate In tetrahydrofuran at 20℃; | 22.1 Step 1: preparation of compound 22b A solution of 6-chloropurine riboside 22a (10.0 g, 34.88 mmol, CAS 5399-87-1) in THF (200 mL) was hydrogenated under atmospheric pressure at room temperature on Pd/C (10% on carbon, 8 g) in the presence of K2CO3 (9.64 g, 69.77 mmol). The reaction mixture was filtered over diatomaceous earth, the diatomaceous earth was successively rinsed with THF and 5: 1 THF/MeOH. The combined filtrates were concentrated under reduced pressure to give crude compound 22b (6.3 g) which was used as such m the next step. ESI-MS: m/z 253.1 I M l i |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With palladium on activated charcoal; water Hydrogenation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76.7% | With ammonia In methanol at 4℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With ammonia In ethanol for 48h; Ambient temperature; | |
77% | With sodium methylate | |
76% | With ammonia In methanol at 0℃; for 30h; |
65% | With ammonia In methanol at -5 - 0℃; | |
31.5% | With Methanol-ammonia In methanol at 0℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 15% 2: 35% 3: 40% | With ammonia In methanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 60% 2: 20% | With ammonia In methanol at 80℃; for 10h; | |
1: 60% 2: 20% | With ammonia In methanol at 80℃; for 10h; also with 15N-labelled compounds, also with the 2',3'-O-isopropylidene derivative, deamination reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 74% 2: 3.3% 3: 7.5% | at 0 - 5℃; for 3h; Irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine for 2h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With trichlorophosphate In various solvent(s) at 0℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tris(p-nitrophenyl)phosphate at 37℃; for 24h; phosphotransferase from wheat, pH 4; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
33% | With sulfurous dibromide In N,N,N,N,N,N-hexamethylphosphoric triamide for 4h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | In dimethyl sulfoxide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | In water for 6h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84.7% | With pyridine at 20℃; for 7h; | |
11.7 g | With pyridine at 20℃; for 2h; | 22.2 Step 2 : Preparation of compound 22c A solution of crude compound 22b (6.1 g) and DMTrCl (11.93 g, 35.20 mmol) in dry pyridine (300 mL) ws stirred at room temperature until complete conversion (ca. 2 h). The reaction mixture was diluted with DCM and washed with brine. The aqueous layer was re extracted with DCM. The combined organic layers were dried over anhydrous Na2S04, filtered, and concentrated under reduced pressure. Purification was done by column chromatography over silica gel (gradient elution; 1 - 5% MeOH in DCM) to give compound 22c as a white solid (11.7 g). 1H NMR (400 MHz, DMSO-r/ FontWeight="Bold" FontSize="10" ) 6 ppm 9.21 (s, 1 H), 8.89 (s, 1 H), 8.74 (s, 1 H), 7.33 (d, J= 6.8 Hz, 2 H), 7 15 - 7.26 (m, 7 1 1). 6.80 (t, ./ 9.3 Hz, 4 H), 6.07 (d, .7=4.5 Hz, 1 H), 5 62 (d, ,7=5.6 Hz, 1 1 1). 5.29 (d, ,7=5.8 Hz, 1 H), 4.78 (q, ,7=5.1 Hz, 1 1 1). 4 34 (q, .7=5.3 Hz, 1 1 1 ). 4.1 1 (q, .7=4 8 Hz, 1 H), 3.72 (s, 3 H), 3 71 (s, 3 H), 3.21 - 3.25 (m, 2 H); ESI-MS: m/z 555.1 | M 1 1 j . |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With water; nickel |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With xylene und Behandeln des Reaktionsprodukts mit methanol.NH3; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With Enterobacter gergoviae CECT 875 in agar In phosphate buffer at 60℃; for 3h; Enzymatic reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose; purine With N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate In acetonitrile at 130℃; for 0.0833333h; microwave irradiation; Stage #2: With ammonia In methanol at 50℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
35% | With pyridine; dmap at 80℃; for 15h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 90.4 percent / Lawesson's reagent / pyridine / 6 h / Heating 2: 85.4 percent / NaOH / pyridine; methanol / 0.08 h / 20 °C 3: 79 percent / Raney-Ni / H2O / 6 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 92.3 percent / pyridine / 4 h / 40 - 60 °C 2: 90.4 percent / Lawesson's reagent / pyridine / 6 h / Heating 3: 85.4 percent / NaOH / pyridine; methanol / 0.08 h / 20 °C 4: 79 percent / Raney-Ni / H2O / 6 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 85.4 percent / NaOH / pyridine; methanol / 0.08 h / 20 °C 2: 79 percent / Raney-Ni / H2O / 6 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 84.7 percent / pyridine / 7 h / 20 °C 2: 53.2 percent / AgNO3 / pyridine; tetrahydrofuran / 14 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 84.7 percent / pyridine / 7 h / 20 °C 2: 53.2 percent / AgNO3 / pyridine; tetrahydrofuran / 14 h 3: 79.3 percent / collidine; 1-methyl-1H-imidazole / acetonitrile / 2 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 33 percent / SOBr2 / hexamethylphosphoric acid triamide / 4 h / Ambient temperature 2: 44 percent / Na2S2O3*5H2O / aq. ethanol / 1 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: POCl3 / various solvent(s) / 1 h / 0 °C 2: 0.08 M KOH / acetonitrile; H2O / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 67.4 percent / H2 / MgO / 10percent Pd-C / methanol / 7 h / Ambient temperature 2: 76.7 percent / NH3 / methanol / 24 h / 4 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 67.3 percent / H2 / MgO / 10percent Pd-C / methanol / 4 h / Ambient temperature 2: 76 percent / NH3 / methanol / 30 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: pyridine / 2 h / Ambient temperature 2: p-toluenesulfonic acid monohydrate (pTSA) / CH2Cl2 / 12 h 3: triethylamine hydrofluoride (TEAHF) / tetrahydrofuran; dioxane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: pyridine / 2 h / Ambient temperature 2: p-toluenesulfonic acid monohydrate (pTSA) / CH2Cl2 / 12 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: pyridine / 2 h / Ambient temperature 2: p-toluenesulfonic acid monohydrate (pTSA) / CH2Cl2 / 12 h 3: triethylamine hydrofluoride (TEAHF) / tetrahydrofuran; dioxane 4: pyridine / 2 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: pyridine / 2 h / Ambient temperature 2: p-toluenesulfonic acid monohydrate (pTSA) / CH2Cl2 / 12 h 3: triethylamine hydrofluoride (TEAHF) / tetrahydrofuran; dioxane 4: pyridine / 2 h 5: diisopropylammonium tetrazolide / acetonitrile / 12 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: xylene / und Behandeln des Reaktionsprodukts mit methanol.NH3 2: palladium/charcoal; MgO; H2O / Hydrogenation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: und Behandeln des Reaktionsprodukts mit methanol.NH3 2: palladium/charcoal; H2O / Hydrogenation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide In nitric acid addn. of nucleoside to soln. of aquated Pt(II) diamine, pH adjusted to 4 with NaOH, reaction time 15 to 120 min (depending on the amine); chromy.; ratio of N1 and N7 bound 1:1 complexes: 0.95; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide In nitric acid addn. of nucleoside to soln. of aquated Pt(II) diamine, pH adjusted to 4 with NaOH, reaction time 15 to 120 min (depending on the amine); chromy.; ratio of N1 and N7 bound 1:1 complexes: 0.75; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide In nitric acid addn. of nucleoside to soln. of aquated Pt(II) diamine, pH adjusted to 4 with NaOH, reaction time 15 to 120 min (depending on the amine); chromy.; ratio of N1 and N7 bound 1:1 complexes: 0.65; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide In nitric acid addn. of nucleoside to soln. of aquated Pt(II) diamine, pH adjusted to 4 with NaOH, reaction time 15 to 120 min (depending on the amine); chromy.; ratio of N1 and N7 bound 1:1 complexes: 0.63; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: pyridine 2: dihydrogen peroxide; methyltrioxorhenium(VII) / methanol; water / 20 °C 3: 1,4-dioxane / 4 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: pyridine 2: dihydrogen peroxide; methyltrioxorhenium(VII) / methanol; water / 20 °C 3: 1,4-dioxane; toluene / 5 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: pyridine 2: dihydrogen peroxide; methyltrioxorhenium(VII) / methanol; water / 20 °C 3: tetrahydrofuran / 2 h / 20 °C 4: ammonium hydroxide / methanol; water / 0.5 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: pyridine 2: dihydrogen peroxide; methyltrioxorhenium(VII) / methanol; water / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With water; oxygen; copper(II) sulfate at 80℃; for 6h; Green chemistry; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47% | With pyridine; water; trichlorophosphate at 2℃; for 4h; | Nebularine 5'-monophosphate [9-(5-O-phosphono-β-d-ribofunanosyl)purine]. To a mixture of freshly distilled phosphoryl trichloride (1.74 mmol, 267 mg, 162 μl) water (1.10 mmol, 20 μl), pyridine (1.9 mmol, 150 mg, 153 μl) and MeCN (7.48 mmol, 307 mg, 390 μl), nebularine (0.396 mmol, 100 mg) was added at 2 ºC added. The reaction mixture was maintained at this temperature for 4 h, poured into ice water, stirred for additional 1 h and neutralized with 25% aq ammonia. The volatiles were removed under reduced pressure, and the residue was purified by HPLC on a LiCroCART 250-10 column eluting with a 97:3 (v/v) mixture of aq. AcONH4 and MeCN. The buffer constituents were removed under reduced pressure. Nebularine 5'-monophosphate obtained as an ammonium salt was dissolved in water and passed through an ion exchange column (Dowex 50WX8). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With nitric acid; In water; at 50℃; for 1h; | 1a(0.142 g, 0.5 mmol) was slowly added to a stirred solution ofHNO3(50%, 5 mL). The mixture was heated to 50Candkeptat this temperature for 1 hour. The solvent was neutralized by1 mol/L NaOH and was concentratedin vacuo.Thesaltswerefiltered and washed with EtOH (5 mL). The mother liquor wasevaporated to dryness and was recrystallized from H2Otogive2aas a white solid (0.103 g, 82% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61 mg | With (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile; trifluoroacetic acid In dimethyl sulfoxide at 40 - 48℃; for 3h; Irradiation; Sealed tube; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With trimethylsilylazide; bis-[(trifluoroacetoxy)iodo]benzene at 20℃; for 0.166667h; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 20℃; |
Tags: 550-33-4 synthesis path| 550-33-4 SDS| 550-33-4 COA| 550-33-4 purity| 550-33-4 application| 550-33-4 NMR| 550-33-4 COA| 550-33-4 structure
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H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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