Structure of 103986-53-4
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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. : | 103986-53-4 |
Formula : | C11H11BO2 |
M.W : | 186.02 |
SMILES Code : | CC1=CC=C(B(O)O)C2=CC=CC=C12 |
MDL No. : | MFCD01632204 |
InChI Key : | JHVQEUGNYSVSDH-UHFFFAOYSA-N |
Pubchem ID : | 2773511 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 14 |
Num. arom. heavy atoms | 10 |
Fraction Csp3 | 0.09 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 2.0 |
Molar Refractivity | 58.74 |
TPSA ? Topological Polar Surface Area: Calculated from |
40.46 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 |
2.44 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
0.83 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.64 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
0.81 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.14 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.99 |
Solubility | 0.189 mg/ml ; 0.00102 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.93 |
Solubility | 0.217 mg/ml ; 0.00117 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.35 |
Solubility | 0.0827 mg/ml ; 0.000445 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 |
-5.7 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) |
1.57 |
* 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 |
---|---|---|
94.6% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; at 80℃; for 24h;Inert atmosphere; | A mixture of 4-methyl-naphthalene-1-boronic acid (5.00 g,26.8 mmol), <strong>[175205-81-9]2-bromo-4-(trifluoromethyl)pyridine</strong> (6.68 g,29.5 mmol), tetrakis(triphenylphosphine)palladium (0.31 g,0.26 mmol, 1 molpercent), potassium carbonate (75 ml, 2Maqueous solution), and tetrahydrofuran (150 mL) washeaded under a nitrogen atmosphere at 80 C for 24 h.This reaction is the Suzuki coupling reaction. After thereaction, the mixture was cooled to room temperatureand the flask was left in an ice bath for 2 h. The compoundwas extracted by liquid?liquid separation (water anddichloromethane). The compound was purified by a celitesilicagel filter (solvent: toluene) and column chromatographyon silica gel (eluent: hexane/ethyl acetate, 15:1).Yield: 94.6percent (7.306 g); 1H NMR (CDCl3, 500 MHz):H (ppm) 8.52 (d, 1H), 8.38 (d, 1H), 8.33 (d, 1H), 8.18(d, 1H), 8.06 (s, 1H), 7.54 (s, 1H), 7.52 (d, 1H), 7.15(d, 1H), 7.09 (s, 1H), 2.26 (s, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With palladium diacetate; potassium carbonate; triphenylphosphine; In 1,2-dichloro-benzene; at 180℃; for 48.0h; | General procedure: To a re-sealable pressure tube (13 x 100 mm) equipped with magnetic stir bar were added o-bromonitrobenzene 1 (0.25 mmol, 100 mol%), aryl boronic acid 2 (0.65 mmol, 260 mol%), Pd(OAc)2 (0.0125 mmol, 5 mol%), PPh3 (1.25 mmol, 500 mol %), K2CO3 (1 mmol, 400 mol%) and o-DCB (1.25 mL, 0.2 M concentration with respect to o-bromonitrobenzene 1. The mixture was heated at 180 C (oil bath temperature) for 48 h, at which point the reaction mixture was allowed to cool to ambient temperature. The reaction mixture was filtered through a pad of celite and the resulting liquor was concentrated in vacuo and purified by flash column chromatography (SiO2) under the conditions noted to furnish the corresponding product. |
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