Structure of 170489-16-4
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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. : | 170489-16-4 |
Formula : | C11H11NO |
M.W : | 173.21 |
SMILES Code : | O=CC1=CN(C)C2=C1C(C)=CC=C2 |
MDL No. : | MFCD11505328 |
InChI Key : | QGFBNIAKXKURCE-UHFFFAOYSA-N |
Pubchem ID : | 22139042 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 13 |
Num. arom. heavy atoms | 9 |
Fraction Csp3 | 0.18 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 1.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 53.55 |
TPSA ? Topological Polar Surface Area: Calculated from |
22.0 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.95 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.83 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.3 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.47 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.55 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.02 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.51 |
Solubility | 0.531 mg/ml ; 0.00307 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.91 |
Solubility | 2.12 mg/ml ; 0.0122 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.18 |
Solubility | 0.115 mg/ml ; 0.000665 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 |
-6.06 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) |
1.38 |
* 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 |
---|---|---|
General procedure: To a cooled solution of DMF (5 mL, 3 mL per 1 mL of POCl3) at 0 C was added phosphorus oxychloride (1.6 mL, 18 mmol) drop-wise, and then the mixture was stirred at the same temperature for 1 h. Then N-methyl indole (ca. 12 mmol) was added as a DMF solution (10 mL), forming a heavy suspension that required vigorous stirring. The mixture was then allowed to warm to room temperature and stirred for 5 hours. Then 2M NaOH (27 mL) was added slowly with vigorous stirring. The mixture was heated to reflux for 20 minutes. Then the reaction was cooled to room temperature and diluted with EtOAc (15 mL) and water (15 mL). The organic layer was separated and the aqueous layer was extracted with EtOAc (2×15 mL). The combined organic layers were washed with water (4×15 mL) and brine, dried over anhydrous Na2SO4 and concentrated in vacuo to furnish the desired aldehyde as yellowish solid that required no further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
EXAMPLE 16 (E)-3-(1,4-Dimethylindol-3-yl)-1-(3,4,5-trimethoxy-phenyl)-2-propen-1-one (Compound 16) Process 1 Compound III-1 (38 mg) obtained in Process 1 of Example 15 was reacted according to the same method in Example 2. The insoluble matters were filtered off, and the filtrate was concentrated under reduced pressure. The residue was subjected to partitioning between ethyl acetate and water, and the organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give 1,4-dimethylindole-3-carboxaldehyde (28.5 mg). 1 H-NMR (90 MHz, CDCl3) δ2.82 (s, 3H), 3.81 (s, 3H), 6.89-7.29 (m, 3H), 7.73 (s, 1H), 10.06 (s, 1H) EI-MS m/z=173 (M+) | ||
Process 2 Substantially the same procedure as in Process 4 of Example 13 was repeated using Compound IIc-1 (83 mg) obtained in Process 2 of Example 13 and 1,4-dimethylindole-3-carboxaldehyde (28 mg) obtained in the above Process 1 except that the reaction product was purified by silica gel column chromatography, to give Compound 16 (13.1 mg). 1 H-NMR (270 MHz, CDCl3) δ2.80 (s, 3H), 3.86 (s, 3H), 3.94 (s, 3H), 3.96 (s, 6H), 7.00 (m, 1H), 7.15-7.30 (m, 5H), 7.69 (s, 1H), 8.48 (d, J=15.3 Hz, 1H) EI-MS m/z=365 (M+) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | With C48H39N3; oxygen; potassium iodide; In water; acetonitrile; for 48h;Irradiation; | Compound 1 (1 mmol) was weighed and dissolved in 5 mL of acetonitrile to dissolve KI (664 mg, 4 mmol) in 1 mL of water and 20 mg. CMP-CSU1, Add to a 25 mL reaction flask and add 300 μl of 2 with a pipette. The LED lamp was continuously illuminated for 48 hours under continuous oxygen supply. The solvent was evaporated to dryness and purified to give the corresponding product 3a (yield: 90%), 3b (yield: 66%), 3c (yield: 72%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With ammonium acetate; for 1h;Reflux; Inert atmosphere; | General procedure: Aldehyde (4 mmol) and ammonium acetate (12 mmol) were refluxed in nitromethane (12 mL) for 1 hour. The solvent was removed in vacuo and the residue washed with water and filtered, furnishing the desired nitro olefin as yellowish solid that required no further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With N,N,N,N,-tetramethylethylenediamine; Eosin; potassium iodide; In water monomer; acetonitrile; at 20℃; for 52h;Irradiation; | General procedure: A 10 mL reaction bottle was charged with 1 (0.5 mmol), TMEDA (2 equiv, 1 mmol), EY (0.1 equiv, 0.05mmol), KI (4 equiv, 2 mmol), MeCN (5 mL) and H2O (1 mL). Under the condition of air, the reaction wasirradiated by two 450 nm blue LED lamps and detected by TLC. After complete reaction, the product 3 wasconcentrated under vacuum and purified by silica gel chromatography with petroleum ether / ethyl acetate. |
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