Structure of 421553-62-0
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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. : | 421553-62-0 |
Formula : | C14H12O2 |
M.W : | 212.24 |
SMILES Code : | O=CC1=CC=C(C2=CC=CC=C2OC)C=C1 |
MDL No. : | MFCD01631913 |
InChI Key : | CFGCKFDEJVKBCY-UHFFFAOYSA-N |
Pubchem ID : | 2759543 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302 |
Precautionary Statements: | P280-P305+P351+P338 |
Num. heavy atoms | 16 |
Num. arom. heavy atoms | 12 |
Fraction Csp3 | 0.07 |
Num. rotatable bonds | 3 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 63.76 |
TPSA ? Topological Polar Surface Area: Calculated from |
26.3 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.26 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
3.27 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
3.17 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.6 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.7 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
3.0 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.57 |
Solubility | 0.0567 mg/ml ; 0.000267 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.5 |
Solubility | 0.0676 mg/ml ; 0.000319 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-5.0 |
Solubility | 0.00214 mg/ml ; 0.0000101 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 |
-5.27 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 |
1.0 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 |
---|---|---|
87% | With sodium carbonate; In methanol; at 20.0℃; for 3.0h;Sealed tube; Inert atmosphere; | General procedure: To a round bottom flask with stir bar were added phenylboronic acid (275 mmol), 1-bromo-4-nitrobenzene (250 mmol), base (375 mmol), 1.0 mol% catalyst 6 (9.2 mg), and solvent 4mL. The entrance was sealed with septum, and inside air was was exchanged with N2. After the mixture was stirred at room temperature for a certain period, the mixture was diluted with H2O (5ml) and Et2O (5 ml). Organic layer was concentrated in vacuo. |
81% | With sodium carbonate; at 90.0℃; for 1.0h; | General procedure: Suzuki-Miyaura coupling was carriedout in a batch reactor using Pd-RGO synthesized with amicroreactor. Aryl bromide (250 mumol), arylboronic acid(275 mumol), and Na2CO3 (0.38 mmol) together with the Pd-RGO synthesized above are added to a 5 mL round bottomflask and stirred at 90C for 1 h. After the reaction, the mixtureextracted with dichloromethane (3 × 5 mL) and impuritieswere removed using celite. MgSO4 was used to removethe remaining H2O, product was obtained from extractedDCM solution through rotary evaporator. We purified theextracted product by the thin-layer chromatography and liquidcolumn chromatography using hexane and ethyl acetate(9: 1). The analysis was carried out via 1H and 13C NMR. |
With tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate; In ethanol; water; toluene;Reflux; | General procedure: Tetrakis(triphenylphosphine)palladium(0) (0.0168 mmol) was added to a solution of 4-bromobenzaldehyde (50, 5.6 mmol) in ethanol-toluene (40 mL, 1:1). After 15 min, the appropriate boronic acid 51b-m (6.75 mmol) was added, followed by sodium hydrogen carbonate (22.4 mmol) and water (11 mL). The resulting mixture was heated under reflux for 9-15 hours. After cooling, the reaction mixture was filtered through Celite, the organic phase was separated, washed with brine (2x20 mL), dried and the solvent evaporated in vacuo. The residue thus obtained was purified by flash-chromatography. Elution by light petroleum-ethyl acetate mixtures afforded the desired compounds. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
EXAMPLE 18 3,4-Difluoro-N-(2'-methoxy-biphenyl-4-ylmethyl)-benzenesulfonamide 2'-Methoxy-biphenyl-4-carbaldehyde-O-methyl-oxime was prepared in a similar manner to 5'-fluoro-2,2'-dimethoxy-biphenyl-4-carbaldehyde-O-methyl-oxime (Example 6) using <strong>[421553-62-0]2'-methoxy-biphenyl-4-carbaldehyde</strong>. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In toluene;Reflux; | General procedure: The appropriate 1-substituted-3-methyl-5-aminopyrazole 46 (1.0 mmol) and the aldehyde 47 (1.0 mmol) were heated under reflux in toluene (50 mL) for 7-9 hours; during this period produced water was removed with the aid of a Dean-Stark apparatus. The reaction mixture was cooled, 2-mercaptopropanoic acid (1.0 mmol) was added and the mixture heated again at reflux for 12 hours. The solvent was removed in vacuo and the residue submitted to medium pressure liquid chromatography. Elution by light petroleum-ethyl acetate mixtures afforded the desired compounds. |
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