Structure of 721-04-0
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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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CAS No. : | 721-04-0 |
Formula : | C14H12O2 |
M.W : | 212.24 |
SMILES Code : | O=C(C1=CC=CC=C1)COC2=CC=CC=C2 |
MDL No. : | MFCD00156689 |
InChI Key : | KRSXGTAVHIDVPM-UHFFFAOYSA-N |
Pubchem ID : | 222171 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319 |
Precautionary Statements: | P261-P302+P352-P305+P351+P338 |
Num. heavy atoms | 16 |
Num. arom. heavy atoms | 12 |
Fraction Csp3 | 0.07 |
Num. rotatable bonds | 4 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 62.65 |
TPSA ? Topological Polar Surface Area: Calculated from |
26.3 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 |
2.7 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.95 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.6 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.29 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.75 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.15 |
Solubility | 0.151 mg/ml ; 0.000711 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.91 |
Solubility | 0.264 mg/ml ; 0.00124 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-5.01 |
Solubility | 0.00205 mg/ml ; 0.00000966 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) |
No |
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) |
Yes |
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) |
No |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-5.68 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 |
0.0 |
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) |
1.63 |
* 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 |
---|---|---|
67% | With copper(l) iodide; oxygen; In 1,2-dichloro-ethane; at 100℃; for 16h; | Take a clean 8mL sealed micro-reaction bottle, add a small magnet, dry, add<strong>[42182-27-4]2-aminoisonicotinonitrile</strong> (71.5 mg, 0.6 mmol),2-phenoxyacetophenone (42.5 mg, 0.2 mmol),Cuprous iodide (0.01 mmol),1,2-dichloroethane (1.0 mL),After heating at 100 ° C for 16 hours under oxygen,The reaction mixture was isolated by column chromatography to give the title compound (42.0 mg, yield 67percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With iodine; In 1,2-dichloro-ethane; at 100℃; for 0.5h; | General procedure: A dried glass reaction tube equipped with a magnetic stir bar was charged with 1 (106 mg, 0.5 mmol), 2 or 4 (141.2 mg, or 207 mg,1.5 mmol), I2 (254 mg, 1 mmol) in DCE (10 mL); stirred at 100 C for30 min. The solvent was evaporated under vacuum, and washed with saturated sodium thiosulfate solution, water, brine. The organic layer was dried over anhydrous Na2SO4, filtered, and concentrated to give the crude product, which was purified through flash column chromatography (ethyl acetate in petroleum ether) to give the desired product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With iodine; In 1,2-dichloro-ethane; at 100℃; for 0.5h; | General procedure: A dried glass reaction tube equipped with a magnetic stir bar was charged with 1 (106 mg, 0.5 mmol), 2 or 4 (141.2 mg, or 207 mg,1.5 mmol), I2 (254 mg, 1 mmol) in DCE (10 mL); stirred at 100 C for30 min. The solvent was evaporated under vacuum, and washed with saturated sodium thiosulfate solution, water, brine. The organic layer was dried over anhydrous Na2SO4, filtered, and concentrated to give the crude product, which was purified through flash column chromatography (ethyl acetate in petroleum ether) to give the desired product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In 2-methoxy-ethanol; at 120℃; for 24.0h;Sealed tube; | Put 0.1mmol oxidized lignin model substrate 1 in a 10mL pressure tube, add 0.01mmol HNO3, 1mL DMSO and 0.2mmol o-phenylenediamine 2,After tightening the cap, heat the resulting reaction solution (the concentration of oxidized lignin in the reaction solution is 0.1 mmol/mL) in an oil bath at 100C for 12 hours,The decomposition reaction is carried out. After the reaction is completed, the obtained product is taken out and the solvent is drained and separated by a column to obtain two nitrogen-containing heterocyclic products. |