Structure of 19014-29-0
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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. : | 19014-29-0 |
Formula : | C12H12B2O5 |
M.W : | 257.84 |
SMILES Code : | OB(C1=CC=C(OC2=CC=C(B(O)O)C=C2)C=C1)O |
MDL No. : | MFCD00433207 |
InChI Key : | DFPCWEXYGPRULG-UHFFFAOYSA-N |
Pubchem ID : | 2832120 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P264-P271-P280-P302+P352-P304+P340+P312-P305+P351+P338-P332+P313-P337+P313-P362-P403+P233-P405-P501 |
Num. heavy atoms | 19 |
Num. arom. heavy atoms | 12 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 4 |
Num. H-bond acceptors | 5.0 |
Num. H-bond donors | 4.0 |
Molar Refractivity | 72.61 |
TPSA ? Topological Polar Surface Area: Calculated from |
90.15 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
0.0 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.26 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
-1.16 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
-0.15 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
-2.18 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
-0.45 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.44 |
Solubility | 0.945 mg/ml ; 0.00367 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.75 |
Solubility | 0.457 mg/ml ; 0.00177 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.44 |
Solubility | 0.934 mg/ml ; 0.00362 mol/l |
Class? Solubility class: Log S scale |
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 |
No |
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) |
No |
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) |
No |
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 |
-6.98 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<0.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
2.32 |
* 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 |
---|---|---|
64% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; water; toluene; for 2.0h;Inert atmosphere; | Under the protection of nitrogen gas to a three-necked flask of 250ml 4,4'- diphenylether hypo-3-boric acid 5.7g (22mmol), M37-220g (44mmol), tetrakis triphenylphosphine palladium 2g, 100ml toluene, ethyl alcohol 60ml, water 80ml and 16g of sodium carbonate is added, and the progress Circulating react for 2 hours. After the results gamcheuk and shown by TLC to stop the reaction when the complete reaction was cooled to room temperature fraction ( ) and washed with water and extract the award and merges the organic phase, dry, rotating dewatering (Spin Dry) through a yellow oil It gained the material.Column chromatography (dichloromethane / petroleum ether) to proceed to a white solid 13.0g was obtained to be 64% yield. |
64% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; water; toluene; for 2.0h;Inert atmosphere; Reflux; | In a 250 ml three-necked bottle under nitrogen protection,(22 mmol) of 4,4'-diphenyl ether diboric acid, 2 g of borate (22 mmol), M37-2 20 g (44 mmol), 2 g of tetrakis (triphenylphosphine palladium), 100 ml of toluene, 60 ml of ethanol, 16 g of sodium carbonate, , Reflux reaction for 2 hours, TLC showed complete reaction. The reaction was stopped, cooled to room temperature, partitioned, washed with water, extracted with water, and the organic phases were combined, dried and dried to give a yellow oil. Column chromatography (dichloromethane / petroleum ether) gave 13.0 g of a white solid in 64% yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; water; toluene; for 2.0h;Inert atmosphere; | A 500ml three-necked flask equipped with a mechanical stirrer fitted under the protection of nitrogen gas4,4'-diphenylether hypo-boric acid 3-phenyl-carbazol--N-25.8g (100mmol),3-bromo-benzothiophene-51g (220mmol), tetrakistriphenylphosphinepalladium 3.5g, 150ml of toluene, ethyl alcohol 50ml, 100ml water and 53g of sodium carbonate for 2 hours dongan Circulating In response to the progress. TLC in gamcheuk and It presented the results to stop the reaction when the complete reaction and then cooled to room temperature, aliquots (Separated ), washed and extracted water with water, through the merging of the organic phase, dry, rotary dehydration (Spin dry) to obtain the oil-phase material as a yellow . a column chromatography (dichloromethane / petroleum ether), this 64% yield was obtained as a white solid 27.8g proceeds. |
64% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; water; toluene; for 2.0h;Inert atmosphere; Reflux; | To a 500 ml three-necked flask equipped with mechanical stirrer and nitrogen protection, 25.8 g (100 mmol) of 4,4'-diphenyl ether diboric acid, 3-boronic acid-N-phenylcarbazole, 51 g of 3-bromobenzothiophene (Toluene) palladium, 3.5 ml of toluene, 50 ml of ethanol, 53 ml of sodium carbonate and 100 ml of water were refluxed for 2 hours. TLC showed complete reaction. The reaction was stopped, cooled to room temperature, partitioned, washed with water, extracted with water, and the organic phases were combined, dried and dried to give a yellow oil. Column chromatography (dichloromethane / petroleum ether) gave 27.8 g of a white solid in 64% yield. |