Structure of 229009-41-0
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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. : | 229009-41-0 |
Formula : | C10H14BNO2 |
M.W : | 191.03 |
SMILES Code : | OB(C1=CC=C(N2CCCC2)C=C1)O |
MDL No. : | MFCD03095137 |
InChI Key : | HNEBXPPPIFWGHH-UHFFFAOYSA-N |
Pubchem ID : | 4192670 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 14 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.4 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 2.0 |
Molar Refractivity | 60.91 |
TPSA ? Topological Polar Surface Area: Calculated from |
43.7 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 |
1.44 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
-0.41 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.56 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
-0.32 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
0.25 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.12 |
Solubility | 1.46 mg/ml ; 0.00764 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.96 |
Solubility | 2.08 mg/ml ; 0.0109 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-1.74 |
Solubility | 3.51 mg/ml ; 0.0184 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) |
No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-6.44 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 |
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) |
1.61 |
* 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 |
---|---|---|
92.78% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In water; toluene; at 80℃; for 10.0h; | 2- (1-Naphthylmethoxy)-6-bromo-3-iodoquinoline(100 mg, 0.21 mmol) was dissolved in 3 mL of toluene,Followed by addingPd (PPh3) 4 (13 mg, 0.01 mmol),Sodium carbonate (43 mg, 0.41 mmol) in 1 mL of water,(4- (pyrrolidin-1-yl) phenyl) boronic acid (48 mg, 0.25 mmol)The reaction mixture was stirred at 80 ° C for 10 hours. 5 mL of water was added and the mixture was extracted three times with dichloromethane. The organic phase was combined and purified by column chromatography (petroleum ether / ethyl acetate 15: 1) to give 99 mg of a yellow solid in 92.78percent yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate; In tetrahydrofuran; water; for 12.0h;Inert atmosphere; Reflux; | 7-Bromo-10- (4-bromophenyl) -5- (4-butylphenyl) -11hydro- benzofluorenone (120 mg, 0.2 mmol)4- (1-pyrrolidinyl) phenylboronic acid pinacol ester,(73 mg, 0.18 mmol), potassium carbonate (276 mg, 20 mmol) and bistriphenylphosphinepalladium dichloride (24 mg, 0.02 mmol) were placed in a 30 mL reaction flask,Under an inert gas atmosphere, a mixed solvent (tetrahydrofuran / water = 4: 1, V / V) sufficient to dissolve the reactant was added and the temperature was slowly raised to the reflux temperature. The reaction was stopped after 12 hours.The reaction mixture was poured into water and extracted with dichloromethane. After several times of washing with distilled water, the resulting organic phase was dried over anhydrous sodium sulfate, filtered and concentrated.After removing the solvent, the resulting mixture was subjected to column chromatography using petroleum ether / dichloromethane as the eluent to obtain the target product in a yield of 63percent. |
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