Structure of 19006-81-6
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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. : | 19006-81-6 |
Formula : | C11H9NO |
M.W : | 171.20 |
SMILES Code : | C1(=CC=CC=C1)C2=CC(=NC=C2)O |
MDL No. : | MFCD07437954 |
InChI Key : | DNUDULSSNHKPHP-UHFFFAOYSA-N |
Pubchem ID : | 598786 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H332-H335 |
Precautionary Statements: | P261-P280-P305+P351+P338 |
Num. heavy atoms | 13 |
Num. arom. heavy atoms | 12 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 51.7 |
TPSA ? Topological Polar Surface Area: Calculated from |
33.12 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.79 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.46 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.45 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.88 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.54 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.23 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.07 |
Solubility | 0.146 mg/ml ; 0.000855 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.8 |
Solubility | 0.272 mg/ml ; 0.00159 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.96 |
Solubility | 0.0187 mg/ml ; 0.000109 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 |
-5.6 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) |
1.55 |
* 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 |
---|---|---|
5-Fluoro-3-[2-(4-phenyl-2-oxo-2H-pyridin-1-yl)-acetylamino]-4-oxo-pentanoic acid (1A-4) was prepared from 4-phenylpyrimin-2-one (Iwasaki et al, J. Med. Chem. 1996, 39, 2696) in a manner similar to that described in Example 2 to provide a colorless solid: IR (solid) 3307.5, 3216.5, 1787.8, 1659.7, 1582.9, 1567.6, 1219.4, 1055.5, 927.5, 763.6 cm-1; 1H NMR (400 MHz, DMSO) delta 2.66 (1H, m), 2.85 (1H, m), 4.31-4.72 (3H, m), 5.28 (2H, m), 6.59 (1H, m), 6.69 (1H, m), 7.51 (3H, m), 7.70 (3H, m), 8.50-8.95 (1H, br); 13C NMR (100 MHz, DMSO) delta 33.2, 34.7, 47.6, 50.8, 51.4, 52.3, 83.6, 85.4, 103.8, 104.0, 104.2 104.3, 115.3, 127.0, 129.4, 129.9, 137.1, 140.7, 151.4, 151.6, 161.9, 162.0, 167.8, 168.2, 172.1, 173.1, 202.7, 202.9; 19F (376 MHz, DMSO) delta -226.8 (t), -231.8 (t), -233.27 (t). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol; acetic anhydride; ethyl acetate; | 4-Phenyl-2-pyridone (D1) A solution of 4-phenylpyridine-N-oxide (8.55 g, 50 mmol) in acetic anhydride (250 ml) was heated under reflux for sixteen hours. Acetic anhydride was then removed under vacuum and the residue was dissolved in absolute ethanol (200 ml) and 80% sodium hydride (1.5 g, 50 mmol) was added in small portions. The mixture was stirred for 2 hours under nitrogen, then evaporated and the residue was dissolved in ethyl acetate and dilute hydrochloric acid. The phases were separated and the aqueous phase was basified (sodium bicarbonate) and re-extracted (ethyl acetate). The aqueous phase was filtered to give the solid product which was recrystallized from ethyl acetate/methanol to give pure product, 3.76 g, Mp 226-230 C. The combined organic extracts were evaporated to give a further quantity (1.58 g) of impure product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
25% | With 6-hydroxyquinoline; potassium carbonate;copper(l) iodide; In N,N-dimethyl-formamide; at 130℃; for 18h; | Synthesis of Lambda/-benzyl-2-(2-oxo-4-phenylpyridin-1 (2H)-yl)isonicotinamide <n="130"/>A degassed mixture of Lambda/-benzyl-2-chloroisonicotinamide (0.25 g, 1.01 mmol), 4- phenylpyridin-2(1 H)-one (0.17 g, 0.91 mmol), potassium carbonate (0.20 g, 1.44 mmol), 8-hydroxyquiniline (0.02 g, 0.14 mmol) and copper(l) iodide (0.03 g, 0.14 mmol) in N, N- dimethylformamide (3.0 ml.) was heated at 130 C for 18 hours. The resulting solution was cooled to ambient temperature, quenched with ammonium hydroxide solution (10 ml.) and extracted with ethyl acetate (2 x 25 ml_). The organic solution was dried over anhydrous sodium sulphate, filtered and concentrated in vacuo. The residue was purified by column chromatography to give Lambda/-benzyl-2-(2-oxo-4-phenylpyridin-1 (2H)- yl)isonicotinamide as a colorless solid (0.10 g, 25%): mp 162-163 0C; 1H NMR (300 MHz, DMSO-cfe) delta 9.43 (t, J = 5.1 Hz, 1 H), 8.73 (d, J = 5.1 Hz, 1 H), 8.24, (s, 1 H), 7.99 (d, J = 7.3 Hz, 1 H), 7.89 (d, J = 5.1 Hz, 1 H), 7.79-7.76 (m, 2H), 7.54-7.45 (m, 3H), 7.36-7.18 (m, 5H), 6,82 (s, 1 H), 6.76 (d, J = 7.3 Hz, 1 H), 4.48 (d, J = 5.7 Hz, 2H); 13C NMR (75 MHz, DMSO-CZ6) delta 164.2, 161.6, 152.7, 152.0, 150.2, 143.6, 139.4, 137.4, 136.6, 130.5, 129.6, 128.8, 127.9, 127.4, 127.3, 121.6, 119.9, 116.8, 105.6, 43.3; MS (ES+) m/z 382.6 (M +1 ). |
A142447 [187392-96-7]
(5-Phenylpyridin-3-yl)methanol
Similarity: 0.78