Structure of 1203578-65-7
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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. : | 1203578-65-7 |
Formula : | C15H10BrN |
M.W : | 284.15 |
SMILES Code : | BrC1=CC=C2C=CC(C3=CC=CC=C3)=NC2=C1 |
MDL No. : | MFCD14702481 |
InChI Key : | QRUXWUPPMOLJKM-UHFFFAOYSA-N |
Pubchem ID : | 17918062 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 17 |
Num. arom. heavy atoms | 16 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 1.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 74.88 |
TPSA ? Topological Polar Surface Area: Calculated from |
12.89 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.9 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
4.59 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
4.66 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
3.92 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
4.7 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
4.15 |
Log S (ESOL):? ESOL: Topological method implemented from |
-5.12 |
Solubility | 0.00214 mg/ml ; 0.00000752 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (Ali)? Ali: Topological method implemented from |
-4.58 |
Solubility | 0.00739 mg/ml ; 0.000026 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-7.07 |
Solubility | 0.0000245 mg/ml ; 0.0000000861 mol/l |
Class? Solubility class: Log S scale |
Poorly 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 |
-4.77 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) |
1.99 |
* 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 |
---|---|---|
94% | With [(η5-C5Me5)Ir(6,6'-dihydroxy-2,2'-bipyridine)(H2O)]OTf2; potassium hydroxide In water for 12 h; Reflux; Green chemistry | Acetophenone (144 mg, 1.2 mmol),[Cp * Ir (6,6 '- (OH) 2bpy) (H2O)] [OTf] 2 (8.3mg, 0.01mmol, 1molpercent), potassium hydroxide (56mg, 1.0mmol, 1.0 equiv.),2-Amino-4-bromobenzyl alcohol (201 mg, 1.0 mmol) and water (1 mL) were sequentially added to a 5 mL round bottom flask. After the reaction mixture was refluxed in air for 12 hours,Cool to room temperature. It was extracted with ethyl acetate, the solvent was removed by rotary evaporation and then purified by column chromatography (developing solvent: petroleum ether / acetic acidEthyl ester) to give the pure target compound in a yield of 94percent |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With sodium persulfate; silver nitrate; trifluoroacetic acid In dichloromethane; water at 25℃; for 0.5 h; | General procedure: A dried glass reaction tube equipped with a magnetic stir bar was charged with 1a (1.5 mmol, 3.0 equiv), Na2S2O8 (0.5 mmol, 1.0 equiv) and AgNO3 (0.15 mmol, 0.3 equiv), 2a (0.5 mmol, 1.0 equiv), DCM:H2O = 1:1 (4.0 mL). The resulting mixture was then stirred at 25°C for 0.5 h. The crude production was diluted with EA and Na2CO3 aqueous solution (1 mol/L) and then the resulting mixture was filtered through a pad of Celite. The filtrate was extracted with Na2CO3 aqueous solution (1 mol/L, 20 mL), and the aqueous layer was extracted with EA (3 × 10 mL). The combined organic layers dried over anhydrous Na2SO4, concentrated in vacuo, and purified by flash column chromatograph to give the pure products. The products were characterized by 1H NMR, 13C NMR, LC-MS. |
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