Structure of 3096-56-8
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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. : | 3096-56-8 |
Formula : | C13H7BrO |
M.W : | 259.10 |
SMILES Code : | O=C1C2=C(C3=C1C=CC=C3)C=CC(Br)=C2 |
MDL No. : | MFCD00010789 |
InChI Key : | MTCARZDHUIEYMB-UHFFFAOYSA-N |
Pubchem ID : | 725831 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 15 |
Num. arom. heavy atoms | 12 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 0 |
Num. H-bond acceptors | 1.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 63.01 |
TPSA ? Topological Polar Surface Area: Calculated from |
17.07 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.41 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
4.32 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
3.66 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
3.27 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
4.31 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
3.59 |
Log S (ESOL):? ESOL: Topological method implemented from |
-4.76 |
Solubility | 0.0045 mg/ml ; 0.0000174 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (Ali)? Ali: Topological method implemented from |
-4.39 |
Solubility | 0.0105 mg/ml ; 0.0000405 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-5.93 |
Solubility | 0.000304 mg/ml ; 0.00000117 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 |
-4.81 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) |
2.2 |
* 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 |
---|---|---|
equipped with a pressure-equalizing dropping funnel 2L three-necked flask, metal magnesium (5.1g, 0.21mol), <strong>[50548-45-3]1-bromo-dibenzofuran</strong> (49.1g, 0.2mol) was dissolved in 450g of tetrahydrofuran, and placed in a constant pressure funnel, a nitrogen, three bottles heated to an inner temperature reaches 65 , through a pressure-equalizing dropping funnel was added <strong>[50548-45-3]1-bromo-dibenzofuran</strong> tetrahydrofuran, was added 1-bromo-time first one fifth of tetrahydrofuran dibenzofuran, after the initiation of the reaction, the remaining portion was slowly added dropwise, for 1.5 h addition was complete, the reaction at the reflux temperature IH, stand.2-bromo-fluorenone (51.8g, 0.2mol) was dissolved in 220g of tetrahydrofuran, and then slowly poured into the above three bottles, the reflux temperature of the reaction 3h, after the completion of the reaction, was cooled to 25 , the above reaction solution was slowly the mass was poured into 200g of 10percent concentration diluted hydrochloric acid, stirred for 15min, liquid separation, the organic phase was collected, the solvent removed under reduced pressure to give a crude product of compound 1, 82.1 g viscous liquid, the crude product of the above compound no purified, was used directly in the next reaction. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | Into a solution of the intermediate a (4.19) in purified THF (50 ml), a 2.5 M hexane solution of n-butyllithium (4.8 ml) was added dropwise gradually at -78 C. After stirring at the same temperature for 45 min, 2-bromo-9-fluorenone (2.59 g) was added. After stirring at the same temperature for one hour and further stirring at ordinary temperature for 2 h, the reaction was terminated by adding an aqueous solution of ammonium chloride. After extracting the organic substances with ethyl ether, the extract was dried over anhydrous magnesium sulfate, and then the ethyl ether was removed to obtain a yellow solid. After dispersing the obtained solid in ethanol, the dispersion was stirred. The solid collected by filtration was vacuum-dried to obtain 4.5 g of an intermediate, which was then dispersed in 40 ml of acetic acid. After adding 12 drops of concentrated sulfuric acid, the dispersion was refluxed for 3 h and then cooled to ordinary temperature. The precipitated solid was collected by filtration, washed with ethanol, and vacuum-dried to obtain the intermediate A (3.98 g, 82% yield). MS: [M+H]+=484 | |
82% | Into a solution of the intermediate a (4.19) in purified THF (50 ml), a 2.5 M hexane solution of n-butyllithium (4.8 ml) was added dropwise gradually at -78 C. After stirring at the same temperature for 45 min, 2-bromo-9-fluorenone (2.59 g) was added. After stirring at the same temperature for one hour and further stirring at ordinary temperature for 2 h, the reaction was terminated by adding an aqueous solution of ammonium chloride. After extracting the organic substances with ethyl ether, the extract was dried over anhydrous magnesium sulfate, and then the ethyl ether was removed to obtain a yellow solid. After dispersing the obtained solid in ethanol, the dispersion was stirred. The solid collected by filtration was vacuum-dried to obtain 4.5 g of an intermediate, which was then dispersed in 40 ml of acetic acid. After adding 12 drops of concentrated sulfuric acid, the dispersion was refluxed for 3 h and then cooled to ordinary temperature. The precipitated solid was collected by filtration, washed with ethanol, and vacuum-dried to obtain the intermediate A (3.98 g, 82% yield). MS: [M+H]+=484 | |
82% | Intermediate a (4.19 g)Was dissolved in purified THF (50 ml)A solution of n-butyllithium in hexane (4.8 ml) was slowly added dropwise at -78 C.After stirring at the same temperature for 45 minutes,2-Bromo-9-fluorenone (2.59 g) was added.After stirring at the same temperature for 1 hour, the temperature was raised to room temperature and further stirred for 2 hours,An aqueous solution of ammonium chloride was added to terminate the reaction.After organic matter was extracted with ethyl ether, the extract was dried over anhydrous magnesium sulfate,The ethyl ether was then removed to give a yellow solid.After dispersing the obtained solid in ethanol,Followed by stirring. The solid separated by filtration was dried under vacuum to obtain 4.5 g of an intermediate.The obtained intermediate was dispersed in 40 ml of acetic acid, 12 drops of concentrated sulfuric acid was added thereto, and the mixture was refluxed for 3 hours. After cooling to ambient temperature, the obtained solid was filtered off, washed with ethanol, and dried under vacuum to obtain 3.98 g (82% yield) of Intermediate A. |