Structure of 94839-07-3
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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. : | 94839-07-3 |
Formula : | C7H7BO4 |
M.W : | 165.94 |
SMILES Code : | OB(C1=CC=C(OCO2)C2=C1)O |
MDL No. : | MFCD01009695 |
InChI Key : | CMHPUBKZZPSUIQ-UHFFFAOYSA-N |
Pubchem ID : | 2734371 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 12 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.14 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 4.0 |
Num. H-bond donors | 2.0 |
Molar Refractivity | 42.33 |
TPSA ? Topological Polar Surface Area: Calculated from |
58.92 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 |
0.64 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
-0.9 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
-0.57 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
-0.69 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
-0.31 |
Log S (ESOL):? ESOL: Topological method implemented from |
-1.58 |
Solubility | 4.4 mg/ml ; 0.0265 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.45 |
Solubility | 5.85 mg/ml ; 0.0353 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-1.03 |
Solubility | 15.4 mg/ml ; 0.0927 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 |
-6.86 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) |
2.57 |
* 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 |
---|---|---|
99% | With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver trifluoroacetate; In methanol; at 60℃;Schlenk technique; Inert atmosphere; | General procedure: A mixture of N-pyrimidyl indoles 1 (0.20 mmol, 1.0 equiv.), arylboronicacids 2 (0.40 mmol, 2.0 equiv.),AgOOCF3 (0.80 mmol, 4.0 equiv.), and [RhCp*Cl2]2(0.002 mmol, 0.01 equiv.) were combined in MeOH (1.0 mL) in a dried Schlenk tubeunder a argon atmosphere. The resulting mixture was stirred at 60 C andmonitored by TLC. Uponcompletion or no further improvement of reaction, the reaction mixture wascooled to room temperature and added with Et3N (1 mL). Then themixture was filtered through a pad of silica gel eluting with 25 mL of CH2Cl2.The solvent was removed under reduced pressure and the residue was purified byflash chromatography on silica gel to afford the desired products. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
27.47% | With palladium diacetate; sodium carbonate; In 1,2-dimethoxyethane; water; at 120℃; for 3.33333h;Sonication; | Methyl 5-chlorothiophene-2-carboxylate (176 mg, 0.996 mmol), benzo[d][1,3]dioxol-5-ylboronic acid (248.03 mg, 1.495 mmol), sodium carbonate (633.70 mg, 5.979 mmol) and palladium (II) acetate (34.97 mg, 0.05 mmol) were added to 1,2-dimethoxyethane (4 mL) and double distilled water (1 mL), and the mixture was stirred at 120 C. for 200 minutes together with ultrasonic treatment and then extracted three times with dichloromethane. The extracted solution was dried over anhydrous magnesium sulfate. The organic solvent was concentrated under reduced pressure, purified by flash column chromatography (n-Hx: EtOAc=3:1) and then dried by a vacuum pump to give the title compound as a white solid (yield: 27.47%). 1H NMR (400 MHz, DMSO-d6) delta 7.74 (d, 1H, J=5.2 Hz), 7.48 (d, 1H, J=3.2 Hz), 7.35 (s, 1H), 7.23 (d, 1H, J=8.0 Hz), 6.97 (d, 1H, J=8.0 Hz), 6.07 (s, 2H), 3.81 (s, 3H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With [2,2]bipyridinyl; potassium fluoride; palladium diacetate; trifluoroacetic acid; In tetrahydrofuran; water; at 80℃; for 2h;Inert atmosphere; Schlenk technique; | General procedure: Under a nitrogen atmosphere, aryl acetonitrile 1 (3mmol), arylboronic acids 2 (6mmol), palladium acetate (5mol %), 2,2′-Bipyridine (10mol %), trifluoroacetic acid (30mmol), potassium fluoride (6mmol), tetrahydrofuran (20mL), and water (10mL) were successively added to a Schlenk reaction tube. The reaction mixture was stirred vigorously at 80C for 2h. After the reaction mixture was cooled to room temperature, saturated sodium bicarbonate (30mL) was added into the solution, and the mixture was extracted with ethyl acetate (10mL) for 3 times. The combined organic layer was concentrated in vacuo. The residue was purified by flash column chromatography to afford desired product 3. |
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