Structure of 38493-59-3
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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. : | 38493-59-3 |
Formula : | C8H9BrO2 |
M.W : | 217.06 |
SMILES Code : | OCC1=CC=C(OC)C(Br)=C1 |
MDL No. : | MFCD01861398 |
InChI Key : | QOUYJSKYVZRGCV-UHFFFAOYSA-N |
Pubchem ID : | 13551346 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319 |
Precautionary Statements: | P305+P351+P338 |
Num. heavy atoms | 11 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.25 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 46.76 |
TPSA ? Topological Polar Surface Area: Calculated from |
29.46 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.27 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.7 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.8 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.95 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.34 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.01 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.53 |
Solubility | 0.643 mg/ml ; 0.00296 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.93 |
Solubility | 2.53 mg/ml ; 0.0116 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.21 |
Solubility | 0.133 mg/ml ; 0.000611 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 |
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) |
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 |
-6.42 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 |
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) |
1.32 |
* 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 |
---|---|---|
98% | With diisobutylaluminium hydride In tetrahydrofuran; hexane at -78 - 0℃; for 1 h; Inert atmosphere | To a solution of methyl 3-bromo-4-methoxybenzoate (12, 2.00 g, 8.16 mmol) in THF (20 mL) was added DIBAL–H (1.00 M in hexane, 20.4 mL) at −78 °C. The mixture was stirred at −78 °C for 30 min and 0 °C for 30 min. To the reaction mixture at −78 °C was added methanol (10 mL) dropwisely followed by saturated aqueous Rochelle salt solution (16 mL) and EtOAc (20 mL). After being stirred at room temperature for 2 h, the aqueous layer was extracted with EtOAc. The combined organic layers were dried over Na2SO4, and then concentrated in vacuo. Purification on silica gel column chromatography (hexane/EtOAc=2:1) gave 13 (1.73 g, 7.96 mmol, 98percent) as a colorless solid; Rf 0.17 (hexane/EtOAc=3:1); 1H NMR (300 MHz, CDCl3) δ 7.57 (1H, d, J=2.2 Hz, H18), 7.27 (1H, dd, J=8.6, 2.2 Hz, H15), 6.88 (1H, d, J=8.6 Hz, H16), 4.61 (2H, s, H13), 3.90 (3H, s, OMe); 13C NMR (75 MHz, CDCl3) δ 55.5, 134.6, 132.4, 112.0, 111.8, 64.4, 56.4; EIMS (m/z) calcd for C8H9BrO2 [M]+ 215.98, found 216.05 |
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