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CAS No. : | 3759-28-2 | MDL No. : | MFCD00001895 |
Formula : | C9H6N2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | GKHSEDFDYXZGCG-UHFFFAOYSA-N |
M.W : | 142.16 | Pubchem ID : | 77368 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.11 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 40.68 |
TPSA : | 47.58 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.1 cm/s |
Log Po/w (iLOGP) : | 1.42 |
Log Po/w (XLOGP3) : | 1.5 |
Log Po/w (WLOGP) : | 1.62 |
Log Po/w (MLOGP) : | 1.08 |
Log Po/w (SILICOS-IT) : | 2.11 |
Consensus Log Po/w : | 1.55 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.0 |
Solubility : | 1.41 mg/ml ; 0.00991 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.11 |
Solubility : | 1.11 mg/ml ; 0.00782 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.95 |
Solubility : | 0.16 mg/ml ; 0.00112 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.28 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280 | UN#: | N/A |
Hazard Statements: | H302-H312-H332 | 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 |
---|---|---|
33% | for 1.5 h; Reflux | The synthesis procedure of (E)-2-(2-(1-phenyl-4,5-dihydro-1H-pyrazol-3-yl)vinyl)benzonitrile (PY-oCN) was performed by the following steps (Fig. 3). At first 2-(bromomethyl)benzonitrile was synthesized also as an intermediate for the next pyrazoline derivative (PY-oCNCN). First 2-methylbenzonitrile (25 g, 0.21 mol) was dissolved in 150 cm3 of CCl4. Equimolar amount of NBS and 0.3 g of AIBN were added. The reaction mixture was refluxed for 5 h and after cooling to 40 °C it was filtered and the solvent was evaporated. The residue was chromatographed on silica gel with DCM as eluent. Only the first fraction was collected. The yield of reaction was 25 g (57 percent). According to the following procedure final compound – (E)-2-(2-(1-phenyl-4,5-dihydro-1H-pyrazol-3-yl)vinyl)benzonitrile was obtained. The 2-(bromomethyl)benzonitrile from the first step of synthesis described above (0.4 g, 2 mmol) and triphenylphosphine (0.524 g, 2 mmol) were dissolved and boiled in dry benzene overnight. The resulting salt was filtered, washed with hot benzene and used without further purification. To the suspension of phosphonium salt in dry THF (25 cm3), under inert atmosphere at room temperature, sodium ethanolate (0.108 g, 2 mmol) was added. The color of the mixture became deep red and after that the solution was stirred for another 30min. After that time the solution of 1-phenyl-4,5-dihydro-1H-pyrazole-3-carbaldehyde (0.348 g, 2 mmol) in dry THF (10 cm3) was added drop wise and was stirred overnight at 50 °C. Next the solvent was evaporated and DCM was added to the orange residue until it became homogenous. The product was purified on silica gel with DCM as eluent. It was crystallized from heptane with yield of reaction 0.325 g (59.5 percent). To obtain – (E)-2-(1-cyano-2-(1-phenyl-4,5-dihydro-1H-pyrazol-3-yl)vinyl)benzonitrile, which is a derivative of PY-oCN, it was necessary to synthesize another intermediate. The 2-(bromomethyl)benzonitrile (5 g, 25.5 mmol), which was obtained before, was dissolved in a mixture of ethanol (50 cm3) and water (10 cm3). Potassium cyanide (2.6 g, 40 mmol) was added to this solution. Then it was refluxed for 1.5 h and subsequently poured onto ice. Deep green-blue solution was extracted with DCM. The extract was dried with MgSO4 and passed on alumina (neutral) in DCM to give yellowish solution. The eluent was evaporated and the residue crystallized from methanol. The yield of the intermediate was 1.2 g (33 percent). The last step of (E)-2-(1-cyano-2-(1-phenyl-4,5-dihydro-1H-pyrazol-3-yl)vinyl)benzonitrilesynthesis was as follows (cf. Fig. 3). Anhydrous sodium acetate was added (0.05 g) to the solution of 2-(cyanomethyl)benzonitrile (0.4 g, 2.8 mmol) and 1-phenyl-4,5-dihydro-1H-pyrazole-3-carbaldehyde (0.490 g, 2.8 mmol), in dry ethanol. Then it was stirred and refluxed overnight. The solvent was evaporated and oily residue was chromatographed on silica gel with DCM as eluent. After evaporation of DCM the oil was dissolved in boiling heptane. After cooling below 0 °C the orange solid precipitated from the solution and then it was filtered. The yield of this synthesis was 0.216 g (efficiency: 26 percent). |
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