Structure of 3433-74-7
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 3433-74-7 |
Formula : | C13H11NO |
M.W : | 197.23 |
SMILES Code : | C1OC2=C(NC3=C1C=CC=C3)C=CC=C2 |
MDL No. : | MFCD04108301 |
InChI Key : | SLGIBJWUMUWIFH-UHFFFAOYSA-N |
Pubchem ID : | 11084798 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 15 |
Num. arom. heavy atoms | 12 |
Fraction Csp3 | 0.08 |
Num. rotatable bonds | 0 |
Num. H-bond acceptors | 1.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 63.46 |
TPSA ? Topological Polar Surface Area: Calculated from |
21.26 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.21 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
3.01 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.79 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.56 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.92 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.7 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.55 |
Solubility | 0.0554 mg/ml ; 0.000281 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.12 |
Solubility | 0.149 mg/ml ; 0.000757 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-4.98 |
Solubility | 0.00206 mg/ml ; 0.0000104 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
High |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg |
Yes |
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) |
Yes |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
Yes |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
No |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
No |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
Yes |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
Yes |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-5.37 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
0.0 |
Ghose? Ghose filter: implemented from |
None |
Veber? Veber (GSK) filter: implemented from |
0.0 |
Egan? Egan (Pharmacia) filter: implemented from |
0.0 |
Muegge? Muegge (Bayer) filter: implemented from |
1.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.55 |
PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
Brenk? Structural Alert: implemented from |
0.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
2.81 |
* 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 |
---|---|---|
4) An N,N-dimethylformamide (110 ml) solution of the compound (9.6 g) obtained in 3), potassium carbonate (8.7 g), and copper powder (710 mg) was stirred at 150 C. in a stream of argon air. After 3.5 hours, the mixture was filtered while it was still hot. The filtrate was washed with ethanol and concentrated under reduced pressure. The thus-obtained residue was dissolved in ethanol (80 ml) and treated with activated charcoal. After filtration, the filtrate was concentrated and dissolved in ethanol (80 ml). A 25% sodium hydroxide aqueous (17 ml) solution was added to the solution and heated under reflux for 1 hour with stirring. After the resulting reaction solution was concentrated under reduced pressure, water was added thereto, and the solution was extracted with ethyl acetate. The organic phase was washed with water and saturated brine, dried over sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure. The thus-obtained residue was purified by silica gel column chromatography (developing solvent, ethyl acetate:hexane=1:10) and recrystallized from hexane to obtain the desired compound (4.4 g; yield, 71%) as a white solid. |
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