Structure of 35578-47-3
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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. : | 35578-47-3 |
Formula : | C14H8Br2O2 |
M.W : | 368.02 |
SMILES Code : | O=C(C1=CC=C(Br)C=C1)C(C2=CC=C(Br)C=C2)=O |
MDL No. : | MFCD00000104 |
InChI Key : | NYCBYBDDECLFPE-UHFFFAOYSA-N |
Pubchem ID : | 96430 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 18 |
Num. arom. heavy atoms | 12 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 3 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 76.95 |
TPSA ? Topological Polar Surface Area: Calculated from |
34.14 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.62 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
4.76 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
4.28 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
3.54 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
4.62 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
3.96 |
Log S (ESOL):? ESOL: Topological method implemented from |
-5.42 |
Solubility | 0.00141 mg/ml ; 0.00000384 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (Ali)? Ali: Topological method implemented from |
-5.21 |
Solubility | 0.00228 mg/ml ; 0.0000062 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-6.46 |
Solubility | 0.000127 mg/ml ; 0.000000344 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) |
Yes |
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 |
-5.17 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 |
1.0 alert |
Brenk? Structural Alert: implemented from |
1.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<2.0 |
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 |
---|---|---|
68% | With potassium hydroxide; In ethanol; dichloromethane; water; | Preparative Example 11 2,3,4,5-Tetra(4-bromophenyl)cyclopentadienone (14) A solution of potassium hydroxide (230 mg, 4.1 mmol) in ethanol (5 cm3) was added to a solution of (13) (3.01 g, 8.2 mmol) and 4,4'-dibromobenzil (3.01 g, 8.2 mmol) in ethanol (45 cm3) at 70 C., and the reaction was stirred at 70 C. for 4 hours. Water (200 cm3) and dichloromethane (200 cm3) were added, and the layers were separated. The organic layer was washed with brine (200 cm3) and dried over magnesium sulfate. The solvent was removed to leave a dark purple solid. The crude product was passed through a plug of silica, and then recrystallized from a dichloromethane/ethanol mixture to give (14) as a dark purple crystalline solid (3.87 g, 68%). |
62% | With potassium hydroxide; In ethanol; for 0.666667h;Reflux; | To a solution of 056 (310 mg, 0.84 mmol, 1 equiv) and 101 (310 mg, 0.84 mmol, 1 equiv) in ethanol (3 mL) was added a solution of KOH (47 mg, 0.84 mmol, 1 equiv) in ethanol (0.5 mL). The reaction mixture was stirred at reflux for 40 mm. The dark redsolution was then cooled down to 0 00. The resulting dark red precipitate was filtered and washed with cold ethanol, affording 102 as dark red crystals (365 mg, 62 %). |
After 4,4v-dibromobenzyl (9.8 g, 27 mmol) and di(4-bromophenyl)acetone (2.0 g,5.4 mmol) were dissolved in 40 mL of ethanol and heated, the mixture was refluxed under stirring for 1 hour. KOH (0.3 g, 5.4 mmol) dissolved in 10 mL of ethanol was slowly added dropwise thereto, and then refluxed under stirring for 30 minutes. The resultant was slowly cooled to give a dark red solid powder. The obtained dark red <n="35"/>solid powder was filtered under reduced pressure, and then dried under vacuum to obtain a starting material represented by Formula k. [114] MS [M+H] 700 |
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