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CAS No. : | 936-05-0 | MDL No. : | MFCD00159675 |
Formula : | C5H7N3O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | JSAQDPJIVQMBAY-UHFFFAOYSA-N |
M.W : | 157.13 | Pubchem ID : | 557356 |
Synonyms : |
Hydroxy Dimetridazole;2-Hydroxymethyl-1-methyl-5-Nitroimidazole
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 5 |
Fraction Csp3 : | 0.4 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 38.44 |
TPSA : | 83.87 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) : | -7.52 cm/s |
Log Po/w (iLOGP) : | 0.86 |
Log Po/w (XLOGP3) : | -0.37 |
Log Po/w (WLOGP) : | -0.33 |
Log Po/w (MLOGP) : | -1.16 |
Log Po/w (SILICOS-IT) : | -1.89 |
Consensus Log Po/w : | -0.58 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -0.79 |
Solubility : | 25.8 mg/ml ; 0.164 mol/l |
Class : | Very soluble |
Log S (Ali) : | -0.93 |
Solubility : | 18.5 mg/ml ; 0.118 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | 0.01 |
Solubility : | 159.0 mg/ml ; 1.01 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.29 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302 | 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 |
---|---|---|
62% | at 140℃; for 48 h; | In a sealed glass tube, formaldehyde (1 g, 33.54 mmol) and 1-Methyl-5-nitro-1H-imidazole (4a) (1 g, 7.8 mmol) solution were added in DMSO (5 mL). The tube was heated at 140 °C for 48 h. After that solution was poured into water (5 mL) and extracted with ethyl acetate (3 x 5 mL). Then mixture was dried (MgSO4) and solvent evaporation under vacuum, gave crude in the form of solid, which was recrystallized (THF/heptane, 1:1) and product (5a) was isolated (0.76 g, 62percent yield) as white powder; m.p. 117 °C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | With ammonia; potassium carbonate In methanol at 50℃; for 18 h; | Cytarabine (243 mg, 1.0 mmol), 2-Chlorocarbonyloxymethyl-l-methyl-5- nitroimidazole (439 mg, 2.0 mmol), sodium bicarbonate (336 mg, 4.0 mmol) and DMA (10 mL) were stirred for 7 days. The suspension was filtered and the filtrate concentrated in vacuo. The resultant oil was triturated with DCM; the suspension was filtered, and the solid was washed with DCM then dried at the pump. The solid was dissolved in methanol and then adsorbed on to flash silica. Column chromatography, eluting with 33percent then 50percent methanol / DCM, furnished an off-white wax (53 mg, 12percent); TLC Rf=0.3, 10percent methanol / ethyl acetate. NMR (500Mhz, DMSO-d6, δ)7.98 (IH, s, HarH), 7.35 (IH, bs, HarH), 5.99 (IH, s, NCHO), 5.86 (IH, bs, HarH), 5.65 (IH, bs, OH), 5.47 (IH, bs, OH), 5.26 (2H, m, HarCH2O), 5.05 (IH, s, OH), 4.08 (IH, bs, CHOH), 3.95 (3H, s, NCH3), 3.90 (IH, bs, OCHCH2OH), 3.73 (IH, bs, CHOH), 3.62 (2H, m, CH2OH) ppm.The 2-chlorocarbonyloxymethyl-l-methyl-5-nitroimidazole used in the above synthesis was prepared as follows: 2-Hydroxymethyl-l-methyl-5-nitroimidazole (314 mg, 2.0 mmol) in THF (10 mL) was added to phosgene (4 mL, 8.0 mmol) and THF EPO <DP n="37"/>(15 mL) at O0C. The reaction was stirred for 16 h then the solvent was removed in vacuo. The crude chloroformate was used without further purification.2-Hydroxymethyl-l-methyl-5-nitroiniidazole was prepared as follows: Methanolic ammonia (3.6 mL, 25 mmol) was added to a suspension of ronidazole (5 g, 25 mmol) and methanol (25 mL). Potassium carbonate (1.75 g, 12.5 mmol) was added and the reaction mixture heated to 5O0C for 18 h. The solution was cooled to ambient temperature then partitioned (ethyl acetate and brine), the aqueous phase was extracted (ethyl acetate); the organic phases were combined, washed (water then brine) then dried in vacuo. The desired product was obtained as an orange solid (2.3 g, 59percent) and was used without further purification. |
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